If there’s one thing that can ruin a first date and ensure a woman’s first impression of you is a bad one, it’s crappy conversation. You need ice breakers, light-hearted queries, questions that provoke banter, laughter, and thought, as well as questions that dig a bit deeper and go beyond the superficial. To save you from endless awkward silences, we’ve compiled 50 first date conversation starters that do all of these things. Plus, they’re backed by professionals who know what they’re talking about. 

Meet the experts: Sarah Jones is a relationship expert, and founder and CEO of coaching website Introverted Alpha, and Sameera Sullivan is the CEO of Lasting Connections, an elite matchmaking service. Read on. Your future dates depend on it.

1. If you could hop on a plane right now, where would you go?

Who doesn’t love to travel? Hermits, that’s who. If she hates planes, road trips, or has no desire to leave her hometown ever, that’s a good indicator of her ambitions and desires (or lackthereof). Otherwise, this question will excite her and you’ll learn what’s most appealing to her, Jones says. It promotes a good back-and-forth between the two of you.

2. What’s something I wouldn’t guess about you?

“This is a great ice-breaker because it’s a little mischievous and flirtatious,” Jones says. “It’s a sign you’d like to know her beyond surface level, while still giving her the freedom to reveal what she wants to share—and doesn’t.” 

3. What are you most passionate about?

This question lets you get a sense of what she feels strongly about and whether she’s spirited and heartfelt. It’s also the perfect way to gauge whether her level of passion is compatible with yours, Jones says.

4. What’s your dream job?

“This is a great query because a dream job merges meaning, passion, and lifestyle,” Jones explains. Better yet, her reason will be incredibly telling. Is it the money, the impact, the enjoyment? Each of these explanations reveals something about her character.

5. What sort of things make you laugh out loud?

If things get a bit awkward or serious, divert to a more carefree topic. Everyone loves to laugh, and talking about the things that make you both fall into a fit—cheesy pickup lines, dad jokes, a particular YouTube flick—gets the conversation flowing… and both of you laughing. Lots of laughter on a first date is a great sign, Jones says.

6. If work was no longer an option and you had plenty of money, what would you do all day?

This conversation starter can bring a light, playful, untethered feeling into your mix of questions, Jones says. “It’s also fascinating to hear anyone’s answer,” she adds. If she’d watch every television series ever created, and you’re an active guy who can’t stand to be indoors, well, that shows you might not be super compatible. 

7. What do you like most about living here?

This question rocks whether you’re new to a city or you’ve lived there for years. “You get to talk about local places she likes, see what you have in common, bond over the people, culture, and why you moved to the area in the first place,” Jones says. Better yet: “Many second date ideas can be born from this question.”

8. What’s been the most significant or best year of your life so far?

If you want the conversation to become a bit reflective, thoughtful, and meaningful, this is a great fall-back. “Not only do you get to hear about her life story, but the snippet that’s most meaningful and important to her,” Jones explains.

9. What’s one thing you did as a kid that you miss most today?

She’ll get a little reminiscent with this conversation starter. It’s playful. And who knows, maybe you went to the same camp or vacation spot each summer. “It’s fun to see what you might have had in common as kids,” Jones says.

Who do you talk to the most?

You’ll learn about the people closest to her in life. Good: You can see if she has a tight bond with her parents or siblings. Bad: You can see if she’s still hung up on an ex. “The five people we’re around the most, shape us the most; her relationship to any one of her closest friends and family members tell you a lot about her,” Jones says

How did you spend your day?

Waiting to be seated at your table or for your waiter to arrive? Break the ice with a simple, straight-forward question like this. “You get a glimpse into her day, her job responsibilities, how she deals with stress, her energy level, tone, and how she spends her time,” Jones says. Those small details and what she chooses to focus on—whether good or bad—clue you in on her personality big time.

Would you go on a cross-country road trip?

This may seem a bit odd and specific, but how she likes to travel is sometimes even more telling than where she likes to travel. Does she only stay in five-star resorts? Is she into sustainable locales? Is she a bargain traveler? Is she up for camping and RVing? All these alternatives offer “insight into her lifestyle, taste, and knowledge about other cultures.” Sullivan says.

In a new city, what attraction do you have to visit first?

Some say you never truly know someone until you travel with them. Odds are you won’t be traveling on a first date, but this question (paired with the above) can offer a ton of clues about her persona. “This opens the door for conversation relating to history, religious perspectives, art, and culture,” Sullivan says. If she’s crazy about museums and monuments, you can infer she’s a history buff—or better yet, ask her if she’s a history buff. Let one question lead to another.

What are 5 things you want to accomplish before you die?

You’ll get major insight on her goals and priorities in life. You can gauge whether she’s philanthropic, an outdoor buff with a killer bucket list, and everything in between.

What is your favorite dish to cook?

“Learn about her culinary skills, what food she likes, if she’s into healthy cooking, and has any favorite restaurants, Sullivan says. Food is always a safe topic of conversation—and an endless one, too.

What are your favorite sports?

“If sports are big in your life, this will take you into a ton of subtopics,” Sullivan says. Ask what sports she’s interested in, what teams she roots for, and if she played sports in college. Depending on her answer, you can see whether you’re up for some healthy competition or standing behind the same teams. And if she doesn’t care, then you can decide whether it’s a slight turn off or a deal breaker.

What are some of your favorite TV shows?

Her interests are reflected in what she likes to watch on a daily basis. Does she only watch educational shows? Is she all about news or talk shows? Is she an absolute reality show junkie? You’ll also find out how much time she spends on the couch.

What did you do last weekend?

If you’re going to be compatible with a woman, you need to have common habits and hobbies. Ask her how she spends her free time! From this, you get a sense of whether she enjoys relaxing or letting loose when she’s away from work.

What kind of books do you like to read?

Is she on the road to self-improvement and solely reads to better herself and her career, or does she read for pleasure? Get into a conversation about what inspires her. “This is a good way to know what her intellectual interests and passions are,” Sullivan says.

Who has been the most influential person in your life?

“Instead of asking how close she is with her family, ask: ‘Who’s the most influential person in your life?'” Sullivan says. “This will tell you more about her family dynamics and close relationships she has with friends.”

Do you still keep in touch with childhood friends?

Unless she moved around a lot as a kid (this should spark questions, too), asking whether she still talks to friends from childhood will reveal how she values relationships and loyalty.

If you were stranded on an island and could take three things with you, what would they be?

Catching her off guard is a good thing so long as your intentions are innocent and playful. Despite the quirkiness of this question, you’ll find out what’s most valuable to her and the significance of those items.

What’s your favorite animal?

Light-hearted questions like this one can stir up memories from her childhood. It’ll also let you know if she’s a pet lover. It may seem silly, but if she hates dogs and your Husky is part of the family, or she’s got two cats and you’re allergic, things might not work out.

What’s the most spontaneous thing you’ve ever done?

Is she a thrill-seeker or a free spirit? You’ll find out if she’s been running with bulls or scaled a mountain. “This is a great question to see how flexible she is,” Sullivan explains. You can see if your personalities and interests jive, too.

What is your biggest pet peeve?

Ask about the little things that drive her nuts. “Obviously you’ll get an insight on her temperament,” Sullivan says. But you’ll also be able to reign in any bad habits that might prevent you from nabbing a second date.

What’s your all-time favorite movie?

“Her answer will reveal whether she has a dark, goofy, nerdy, romantic, sappy, or quirky side,” Sullivan says. Plus, you won’t be blind-sided if you make a movie date and you’re stuck sitting through a rom-com. 

How do you like to spend your mornings?

It might seem super particular, but her morning routine is hugely revealing. Does she wake up, get ready, and rush to work with minutes to spare? Does she wake up, lounge around, read a newspaper, then get ready for work? Or does she meditate, go for a six-mile run, shower, and make a gourmet breakfast before heading out the door? These scenarios are snapshots of three incredibly different people and personality types.

How do you like to spend your nights?

Like the previous question, this one clues you in on how she spends most of her time and whether you’ll enjoy the same activities. You may love going out to bars and clubs for karaoke on a Saturday night while she’d rather binge-watch the latest Netflix series. You’ll see early on whether you’ll clash.

What are your quirks?

Maybe she leaves the TV on when she sleeps or likes to eat ice cream with a fork. This gives you a chance to see if she has any quirks that are endearing… or a turn off. 

What’s you all-time favorite song/artist/band/genre?

“Asking about her favorite song, band, or artist of course tells you about her taste in music,” Sullivan says. But you can branch off and find out what her first concert was, who she’s dying to go see, and if the cards work in your favor, these bits of information can turn into a phenomenal future date or surprise.

What are you most afraid of?

This question can go the trivial or serious route. Try both. See what childhood fear she still has: Maybe she’s terrified of spiders, darkness, and basements. And ask what she’s most afraid of in life: Is she afraid of failing in her job, never getting the opportunity to travel, mending a particular relationship? You’ll see a vulnerable side of her without being too forward.

Tell me about your family.

Yes, this is a popular first-date question, but for good reason. Go ahead and ask the basic questions about how many siblings she has and how big her extended family is and let the answers lead to deeper, more meaningful ones. It shows you care and are invested in learning who she is from her roots and where she came from.

Who’s your best friend?

This may or may not be the same person she spends the most time with, but both people are obviously key to who she is. If her best friend is someone she grew up with or someone she’s close with because of a particular incidence (good or bad), ask her about it. This is someone she cherishes in life, so it’s a sweet gesture to show a genuine interest in that person, too.

Are there misconceptions about yourself you wish people wouldn’t make?

This is a ballsy question, so use your discretion. In the right context, though, it can let her clear the air or dispel any frustrating assumptions people make about her. Let her take this question where she wants, and don’t be too pushy.

If you were to patent an idea or thing, what would it be?

This question gives you major brownie points for being clever. You can see how her brain works and how clever she is, too! 

What do you wish you were better at?

Ask her what skills she wants to acquire or hone in her career and life in general. If she’s ambitious, that can be a major turn on. It’ll also show you she’s humble and doesn’t hold herself too high if she points out some areas she wants to improve.

What’s been your biggest regret in life?

Like some of the other questions on this list, feel out the conversation and only ask this one if the moment feels right as it could make her feel uncomfortable. Try to slip it in to conversation if she mentions a career path she could have gone down or a trip of a lifetime she never took. Just tread lightly.

What would you be doing if you weren’t in your current job?

This is a twist on the “dream career” question, but will result in an answer like “lawyer” rather than “movie star.” What she went to school for may not be the field she’s in now. Likewise, what she studied in school may not be her dream career anymore. This is a fun way to pick her brain and get her talking about what her interests and passions are.

What did you want to be growing up?

You can use this question as a preface or follow up to No. Both of you get the floor to speak about your childhood. You’ll have endless stories… chock-full of embarrassing confessions and lofty dreams.

What was your yearbook quote?

High school is a time of awkward stages and thinking you’re funny when you’re really not. Ask her what her yearbook quote was. If she didn’t have one, ask what it would have been, or what she would make it now?

What’s the worst pickup line you’ve ever heard/dished out?

The experts agree: There’s nothing wrong with getting a little flirtacious on a first date. Ask her for some of the worst pickup lines she’s heard. You’ll get some laughs and can try some cheesy ones out on one another. A little banter is a good sign that your humor is in sync.

What’s the last event you bought a ticket for?

If she’s going to dish out $+ on tickets for a Broadway show, sporting event, or concert, it shows it’s important to her and something she thoroughly enjoys doing. It’s a roundabout way of seeing what her interests are in detail without straight out asking.

What’s your favorite childhood memory?

You want positive vibes only on a date. By posing this question, you get her thinking about some of the best times in her life. You’ll also get a peek into family traditions and dynamics.

Are you closer to one of your siblings?*

You’ll find out how close or far in age she is with her siblings, how many brothers and sisters she has, and how they interact with one another. If you’re big on family, this question is a must.

*Of course, this only applies if you’ve already asked about her family and she does, in fact, have more than one sibling!

Did you have any nicknames growing up? Now?

You’ll get her laughing with this one. Sure, it might be a little embarrassing, but the stories behind the nickname will make for perfect, light-hearted conversation.

What’s the most embarrassing thing that’s ever happened t

Share a funny story at your own expense first. It’ll show her you have a sense of humor and can laugh at yourself. Then, she’ll be more inclined to do the same.

Do you have any hidden talents?

Maybe she’s a classically trained pianist or was a champion cup stacker in her youth. When you ask the right questions—even ones as simple as this—it can unveil a goldmine of information.

What talent do you wish you had?

See what talents she admires. If she’s always yearning to learn something new, it shows she’s inquisitive. It can also open the idea of trying something new together—like cooking—on a second date.

Where can you see yourself living?

This question is more revealing than you’d think. If she has plans to move to Toronto next year, she might not be in a place in her life where a long-term relationship is feasible. Likewise, if you’re deadset on living in a city, whereas she’s dying to live on a farm, there are going to be conflicting desires that can spell disaster for a relationship.

What’s your favorite way to get active?

If you’re on this website, fitness and health are obviosuly important to you. Instead of asking her if she works out, see what her favorite physical activities are instead.

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This list of questions to ask a girl over text is just what you need.

I have written countless blogs about questions to ask a girl, so if you want to know how to text a girl you like, you're in luck. This list has all the best questions to ask to keep a good talk interesting. Trust me.

Let's dive right in!

Contents

7 Conversation Starters For Her Online

Most of the time, it seems like finding the right way to start a text message exchange can be the hardest part. If you're already in a relationship, conversation starters for couples can focus on what you already know about each other – but what if you've only just met the woman you're thinking about texting?

Here's the deal: If you've only recently got a girl's number, your conversation starters have to take a different tone. After you've said a friendly hello, start with easy questions with the widest variety of possible answers.

1. What's the best thing that's happened to you today?

Keep it positive! Instead of asking, "how's your day?", lead the discussion in a better direction right from the start. This is a good question to ask when you want to make a good day a better one. This is also the right question to ask after a date because you're ending it on a good note by reminding her of the good things that happened that day.

2. What kinds of things really make you laugh?

Even just thinking about funny things puts her in a better mood, which starts the chat warmly and positively. This is a fun question to ask because you'll know about her sense of humor and if you laugh at the same things she does. Who knows? It may even be the start of true love.

3. What's your favorite place in the entire world?

This is one of the cute ways to hint at asking her out. Use this conversation starter to start planning where you might be able to meet up together later. If she says her favorite place in Italy, well, then maybe it's time to plan a good old romantic gesture and surprise her. It might be the craziest thing, but if you pull it off, good for you!

4. Favorite movie of all time?

Remember that movie you just couldn't get enough of as a kid? Bring back those nostalgic memories by starting an exchange with this question. It's always an interesting conversation when you talk about a favorite thing or a favorite memory. It lets you get to know the other person more.

5. What’s your biggest goal in life right now?

This opens the door to talking about similarities between things you're working on in your lives. This is a great question to ask when you want to know if she's a good fit for your future. Often, a romantic relationship doesn't work out because a couple doesn't talk about their goals. When what they want doesn't match, it creates problems. Avoid that by asking this early on.

6. What is your favorite way to spend a Saturday?

I know some people hate small talk, but this might actually help you plan a good date for her. Planning ahead to the weekend gives you time to prepare for the things she likes. It also builds excitement for the date, so make sure to live up to the hype.

7. What kind of music do you listen to?

Look for shared passions in music or an opportunity to share new music with each other down the road. It's actually an interesting question to ask because learning about someone's taste in music lets you peek into their mind. What kind of artists does she like, and what kind of music do they make? Knowing these helps you get to know her better.

8 Topics To Talk With Her Through Messages

These questions are our go-to favorites. If you're ever at a loss as to how to continue texting a girl, choose one of these to inject new life into the conversation.

8. What kind of trouble are you getting into today?

Playful and cheeky, this text leaves it up to her to imagine what you mean by "trouble." A flirty text like this can be the start of a fun conversation between you two. Keep it going with more flirty questions, and who knows? Maybe she'll be getting in trouble with you next time.

9. If you could travel the world, where would you go?

This may seem like a random question, but whatever her answer is, you can easily build on it by asking what interests her about that place. Share your travel goals and see if you have the same ones. You might even end up making plans to go there together.

When was the last time you got into trouble?

The subtext of this text asks whether she's willing to take risks (even if she gets caught!). Plus, you'll get to know how much of a rebel she is. You'll know if she's spontaneous and courageous enough to actually get in trouble.

What's the most perfect dipping sauce?

Rick and Morty know the importance of the perfect dipping sauce Does she? This may be a random question, but it's good to ask for future reference. Once you know this, the next time you get some fries for her, you'll know to get her mayo instead of ketchup.

If a genie appeared to grant you one wish, what would you wish for?

What does she want most in her life right now, and how does that relate to you? If she answers that her wish is to be your girlfriend, that certainly is the biggest turn of events ever. If it's not that profound, maybe she'll just wish for her celebrity crush to take her out on a date. Either way, it makes a great conversation starter.

If you could be any animal, which would you choose to be? Why?

Her answer will reveal how she thinks of herself, giving you more info on how to make a connection with her. She'll definitely ask you this back, so be prepared with a witty answer to keep the talk going. Don't go with the usual. Think of rare animals like a panther or a stingray. I don't know what kind of conversation this will lead to, but it's going to be an interesting one.

What sport would you never want to play?

Even if your dream girl is amazing at a lot of things, she's always going to have weaknesses. Knowing a girl's limits can help you understand what's most appropriate to talk about. You can also ask her the reason for not wanting to play that particular sport.

If you could have one superpower, what would it be and why?

Her choice will reveal something about what she would most like to change about herself right now. Ask her what she will first do with the superpower she chose. If she wanted to fly, ask where she'd go. If she wanted to have super strength, ask what she'd try to lift first. When she asks you what superpower you want to have, say that you want the ability to have super speed so you can be there for her whenever she needs you. If that doesn't make her smile, I don't know what will.

What is something that is popular now that annoys you?

You can bond over mutual annoyances with this text. Get her talking about all the overrated and overhyped trends the kids are doing nowadays. Share your pet peeves as well, and see if she hates the same things you do. She'll feel comfortable sharing her thoughts with you if she knows you like listening to her rant about stupid things.

7 Flirty Phone Messages That Will Catch Her Attention

After you've broken the ice with a conversation starter, it's time to start flirting with her over text. First, take these tips (from her), and start using and second:

If you could be invisible for the day, what's the first thing you would do?

The subtext of this asks: "What would you do if you could get away with it?" It says a lot about her when she'd do something illegal or downright disturbing. But, it wouldn't be the worst thing to know what things she would do if she could get away with it.

Have you ever been caught doing something you weren't supposed to?

If she answers "yes," she may not want to tell you what – making for a fun guessing game of trying to figure it out. A flirty question like this invites a follow-up question of: "Would you do it again with me?" Try it out, and let's see what kind of response she gives.

via: Pexels / Pixabay

When was the last time you did something outside of your comfort zone?

This might be one of my favorites because it lets you gauge where you're at as far as her comfort levels go. Sometimes, conquering your biggest fear starts with taking steps outside your comfort zone. Get her talking about her little wins and praise her for them.

Ever been in love with two people at the same time?

It carries a powerful subtext: What has her love life been like? Find out what she did to resolve her feelings. If it involved letting one person go, ask how she did it. You'll see how she values people who value her and how she makes decisions.

Have you ever broken someone's heart?

You'll find out whether she has a little bit of "bad girl" in her with this personal question. You can also ask her how she felt about it and if it's something she still thinks about to this day. You can even ask her why she felt the need to break that person's heart. That way, you can avoid doing the same thing.

Can you wiggle your nose or your ears?

This is a cute question to ask since she'll automatically laugh when you ask. Strictly because it's cute, and she'll probably have to try and do it (for you). Pair it with a comment like, "I know it's supposed to be funny, but you just look so cute when you try." You won't see it, but her heart will do a little flutter, I guarantee it.

What do you think of tattoos? Do you have any?

This is a sly way of asking her about her body without it being obviously sexual. Dirty questions only become dirty if you're creepy. So, ask her respectfully and don't pressure her to answer if she doesn't want to. If she does respond, make sure that she's comfortable talking about it. If she looks a little queasy, change the subject and find another topic that she's okay with.

 6 Funny Things To Tell The Woman You Like

Mark Twain once said that "humor is mankind's greatest blessing." Having a good selection of funny questions to ask can instantly brighten an otherwise dreary day.

Being willing to put yourself out there and try to make someone laugh is a huge sign of confidence and a big turn-on for women. Equipping yourself with a few funny questions to ask is a sure way to keep your chat going smoothly.

If you had to make out with a friend of the same sex to save the world from aliens, whom would you pick?

This is a funny but high-risk question. Save this one for when the talking is already going very well. Ask carefully because she may think this is the weirdest thing she has ever been asked. You can even share your pick to make her feel comfortable about sharing hers.

Who would you want to be tied to for 24 hours?

And how would you want to be tied? The funny (and flirtatious) scenarios you can make up out of this are nearly endless. You can even act it out as if you're tied to each other. Say things like, "If we never get out of this, I want you to know that your dog peed on me the other day, and I never said anything." If that doesn't make her laugh, I don't know what will.

Do one-legged ducks swim in circles?

If the conversation is getting a little boring, you should try this one out. There's still a place for good one-liners and rhetorical jokes, too! You could never go wrong with a good old funny question. Try asking this in a serious face and see if she can answer without laughing.

Would you consider yourself obsessed with anything/anyone?

Does she have a collection of Pusheen stuffed animals? A complete Pokedex? No matter what it is, you can kind-heartedly poke fun at her obsession. A guilty pleasure here and there never hurt anyone, so make sure not to make fun of her too much. Do it just enough to keep the texting going.

Do you like to sing in the shower or the car when no one is around?

Follow-up: What do you sing? Find out her favorite song to sing when she's alone. Bonus points if you can get her to voice-record it! The next time you get into a car with her, play a great dance tune and turn that volume up. And don't forget to sing along with her!

Do you still wear a piece of clothing you wore during your childhood?

Like Linus's comfort blanket, there's something inherently funny about juvenile habits. Plus, if she does have something like this from her childhood, getting her to talk about this will open up a good conversation. You can also show up in a small t-shirt you've had since you were a boy to make her laugh.

7 Conversation Lines That Will Help You Know Her Better

By knowing the right questions to ask to get to know a girl, you open the door for building more comfort and connection. With a good introduction, and after a little bit of funny and flirty conversation, you can begin to build the comfort that will lead to a face-to-face date.

Essentially, all of these get to know you questions are made with a goal in mind of learning her preferences, positive and negative, so that you can better plan what sort of activities you can do together.

Which bad habits of people drive you crazy?

Getting to know a woman means asking what she likes and what she dislikes. You can also ask her why those particular habits get her all worked up.  It will give you an advantage because you'll know the things to do and the things to avoid.

Who was the last person you hugged?

Don't let a non-consensual hug be your biggest regret. Some girls are huggers, and some aren't – either way, it's important to know for the next time you see her. Make sure she's always comfortable with you. That's the only way she'll keep entertaining your company.

How would you change the world if you were to play God for a day?

Learn what she's passionate about with this question. Does she want to change any laws? Does she want to change how countries are divided? Whatever it may be, make sure to keep an open mind and really discuss this with her. It may be the start of a deep conversation, especially when she starts talking about what she's passionate about.

If you had to eat 1 thing for the rest of your life, what would it be?

You are what you eat - meaning that the type of food a woman chooses says a lot about her personality. A person's favorite food may be as simple as bread or mashed potato. But, if you had to eat it every day for the rest of your life, would it still be your favorite? Probably not.

Name three things you have never done and don't want to do?

To really get to know her, it's important to know her preferences and her limitations. You can also ask her why she's never done those things. She'll most probably talk about her childhood or her past experiences. These will certainly help you get to know her better.

What are the 3 most important things in a kitchen and why?

Because let's face it: Anyone who knows their way around a kitchen instantly becomes more attractive. And anyone who can make a great meal is a godsend. Find out if she's got what it takes to be a master around the kitchen.

What are you allergic to?

Maybe not the most creative question, but it is essential to know if you plan to ask her out to eat. It's also good to know this so that when you plan to make her some dinner, you'll know what things to avoid. You don't want to end your date in the emergency room, right?

7 Worthy Things To Talk About With Your Girlfriend

So what happens to texting once you're in a relationship?

Well, to tell you the truth a lot of guys make a big mistake. They stop texting their girlfriend like they did when they were first getting to know each other, and that makes text conversations go stale.

You know what, though? I don't think you're that type of guy. So let's keep finding exciting and worthwhile questions to ask a girlfriend over text, whether you've been dating for 2 months or 2 years.

Tell me the truth…how many selfies do you have on your phone?

Being lighthearted and playful with texts like this helps to keep that spark in your relationship. She might be a little embarrassed at first. But sometimes, you just have to share some embarrassing stuff about you so she'll feel comfortable opening up to you.

What is (or was) your least favorite class/teacher?

It's just as important to know what your girlfriend dislikes as it is to know what she likes. Ask her why she didn't like that class or teacher and what she would have changed about them. Often, people know how to complain but not how to solve what they're complaining about. See if she's one of those people.

What do you do when you're bored?

Up next: Invite her to text you funny pictures when she's bored! Or, do one better and send her funny memes when you know she's having an uneventful day. You might just be what turns her boring day into a memorable one. It's always good to make your girlfriend smile, even if it's just through a text message.

If you find $ on the floor right now, what would you do with it?

It's not winning the lottery, and that's a good thing: this gives you an attainable goal of something that would make her happier. To keep the conversation going, tell her that if that happened to you, you'd be taking her out on a fancy date.

Do you think you could give up technology for a week?

Because how often do you get to spend time together without being on your phones or computers? You could even turn this into one of the best dare questions ever. Challenge her to do this with you and see who can't resist being on their phone.

What's the most played song on your iPod?

Knowing what your girlfriend listens to in the privacy of her headphones is a special sort of intimacy. If she tells you, try listening to it to get a feel of what she likes. If this is the most played song, it's probably one that gets her feeling calm or relaxed.

What's the lamest joke you've ever heard?

I always say no joke is too lame when you can deliver it well. Ask her to bring out her best dad jokes! All the better if this starts an awful joke text contest between you. It will get her laughing and smiling, too. She might even tell her friends about it because of how much she enjoyed it with you. Win-win!

7 Personal Things To Talk About With Her

It's surprisingly easy to make a text conversation more personal. You just have to have the right personal questions to ask.

We've compiled a list of personal questions to ask a girl that work great over text.

Below you'll find the best of them.

What is the best/worst/embarrassing/weirdest text message you've received?

She probably has a hilarious screenshot of it. Let her tell you what she felt when she received it and ask how fast she sent it to her friends. Be wary if she mentions a text you've sent. Her friends might have already stalked you way too much on your socials if she's already sent them a screenshot of your weird text.

Have you ever dropped a phone in the toilet?

Not exactly a romantic question, but it's good enough to keep a conversation going. If your phone gets wet, they say to place it in rice. It might absorb the moisture. Also, don't plug it in immediately after it dries up in the rice. Wait another couple of hours before you do to make sure that it doesn't electrocute you.

Which app do you suggest I install on my phone?

We all have our favorite apps that not all people know of. Some of them may be for food deliveries, games, and anything that may interest her. There are millions of apps out there you haven't heard of. I recommend ours.

What is the best selfie you've taken with your phone? Send it to me.

She won't send you photos if you don't ask. Don't be creepy, though! If she shows any form of discomfort at all, immediately tell her that it's fine if she doesn't want to send you photos. Gentlemen, be respectful even when you're trying to poke fun or keep a conversation going. It's important that she feels safe with you.

What is the current wallpaper on your phone?

If it's something artsy, you can get an idea of her aesthetic. If you're at that point, you can even try matching wallpapers with her. Some couples have matching shirts or shoes, but try this out first if you want to start with something small.

What was your last watched YouTube video? Send it to me.

You can spend hours sending silly videos back and forth. It's hilarious and tons of fun. Plus, it gives you something to talk about that you're sure she's interested in. Otherwise, she wouldn't have watched it.

What is the first thing you do with your phone after you wake up in the morning?

This opens up the topic of morning routines. Find out the things she prioritizes in the morning. She'll probably check emails or messages first to see if anything from work popped up. Or, if she's the type to work only during her time of duty, she'll probably scroll through her social media first. Either way, you'll know more about her when you find out the first things she checks when she wakes up.

8 Personal and Deep Topics To Talk About With a Woman Through Messages

It's like this: Whether it's a woman that you've just met or your girlfriend that you've been seeing for a while, you always need to be learning more deeply about them.

Having deep questions to ask a girl will bring you two closer together – just like choosing deep questions to ask your girlfriend will solidify the connection that you've already been making.

By removing the necessity for an immediate response, having a few deep questions to ask over text can lessen the tension of being put "on the spot." This gives her more time to come up with a thoughtful answer. How much you share is up to you, but it's essential to test the waters.

If you choose any 3 people to be stranded on a desert island with, who would you choose and why?

The people we choose to spend time around deeply influence who we become. This question will let you know who she is most deeply influenced by. If she chooses you, then sit down and relax. You're doing a good job as her boyfriend.

If you were guaranteed honest responses to three questions, whom would you question, and what would you ask?

Is there anyone in her life who she hasn't been able to trust? This will tell you what it is that she questions most deeply in her own life. If she says she'd like to ask you something, be the bigger man and don't make an issue about it. Tell her frankly that she doesn't need to include you because you'll tell her the truth every time.

If you were walking through the forest and you suddenly saw a tiger, what would you do?

Run, freeze, or fight – whichever route she chooses says a lot about how she reacts to life's stresses. Her answer will also help guide you when it comes to solving her problems. Follow it up with, "If you run or freeze, would you like me to fight for you?" Sometimes, women don't want to feel helpless, so asking them what you can do for them is important to do.

Who had the biggest impact on the person you have become?

Mentors are critical to our growth – who has helped her become who she is today? Ask her how they have made that kind of impact on her. When you find out what they did, it will help guide you on making a significant impact on her life.

Do you think the future will be better than the present? Why?

This question asks her whether she thinks her own life will get better, as well. To steer the conversation into your future together, follow it up with a comment like, "I am certain the future will be better than the present because I know we'll still be together."

What lies do you most often tell yourself?

Everyone deceives themselves to a certain degree, but being aware of this is what helps us grow. Is she aware of her own little lies? Also, we sometimes tell lies to ourselves because we're afraid to face reality. Asking this question may help her realize the lies she tells herself and try to avoid them from now on.

What are the most common roadblocks that stop people from achieving their dreams?

Sharing your goals and dreams and what is preventing you from them helps develop a closer and deeper relationship. Talking about this will also help you steer clear of the roadblocks to reaching your goals.

What keeps you up at night?

Sharing her worries will let her open up more intimately with you. Plus, when she answers this honestly, you'll know that she's good at sharing her weaknesses with you. It's a good thing to know because you'll be able to ask her even more personal questions without hesitating.

Downloadable and Printable List of Questions to Ask a Girl Over Text

Here is a downloadable and printable jpg/pdf list of questions to ask a girl over text (right-click the image and select Save Image As):

Frequently Asked Questions

If you have more questions, we have answers. We answer your deepest questions about questions here, so that we can clear everything up.

If a girl I like dodged my questions over text, am I friendzoned?

I know it can be frustrating when your jokes or lines don't get recognized over text, and sometimes, that's just the way it is. It doesn't automatically mean you're friendzoned. You'll have a good sense of being in the friendzone if she shows no interest at all.

Knowing how to get out of the friendzone is tricky, but possible. Just make sure you're absolutely clear that you like her and you want it to lead to something more.

How can I ask a girl for her number?

Meeting a girl for the first time can be nerve-wracking. Getting her number may be the goal but before that, you should get her to feel comfortable around you. If she feels the conversation is something she wants to continue, I bet she'd give you her number without you needing to ask. But, if you really want to know how to get a girl's number, asking politely and directly is the best way to go.

How do you know if a girl is interested in you over text?

Knowing if a girl is interested over text is easy. If she responds to you all the time, even when the topic is boring or going nowhere, you're good. Plus, if she thinks of weird ideas and topics to share with you, you know she wants to continue the conversation.

Should I retry messaging her if she ignores my messages?

Wondering what to do if she didn't text back? Sending one more probing text is okay. But, if she doesn't text you back for a few hours or days, maybe it's time to move on. Find a girl who does respond.

How can I make a girl like me over text?

Making a girl like you over text is easy if you follow a good timeline. You can text her for a few days, making little hints about meeting up with her. But, make sure that you're texting her to get her to go out with you. Then, she'll know that you're not just texting her for fun. When she knows that you're interested to meet with her, she'll admire your confidence and honesty. You've got a good chance when she knows your intentions.

How to Start a Conversation with a Girl Over Text

Here are four powerful tips for how to start a conversation with a girl over text:

1. Greet Her Warmly and Politely

Before you start asking a girl questions over text, say "hello" in whatever polite way you'd like. Not only does this show that you have manners, but it also lets you know that she is actively on her phone when you receive a message from her. This way, she will see your message and be more likely to continue the conversation with you when you ask your question.

2. Have a Goal in Mind

What is it that you're looking for out of the conversation? If you start with a goal in mind, then you can plan ahead for how to continue the conversation.

Whether you're looking to build her interest in you or ask her out on a date with you this weekend, having a clear idea of what you're looking for will help you plan how to get there.

3. Ask Questions That Make Her Think

While "how is your day?" may look good on paper,  it's not specific enough to develop an ongoing conversation. Basically, if she can answer the question without thinking, she is less likely to be interested enough to keep texting.

So here's the deal: Asking her questions that make her think will capture her interest. And you want to be interesting to her, right? This article has great tips from her on how to keep a conversation going.

4. Gauge the Tone of the Conversation

via: Unsplash / Sam Balye

If she's replying with one-word answers, don't try to force the conversation. Instead, wait for another time and try again later. It may just be that she's too busy to have a meaningful conversation.

Look for signs that she's interested and engaged, like longer responses or happy emoticons, before trying to move on to new questions in your conversation, and that's how to start a conversation with a girl over text.

Looking for More Questions to Ask a Girl Over Text?

With all of these questions at your disposal, you should be totally set to start texting any woman that you're interested in getting to know better. If you've used some of these successfully and are looking for more, we've got you covered:

1. A lot of questions to ask your girlfriend are just as applicable to a woman that you're not dating (yet!).
2. Need a few questions to throw out there anytime? Check out these random questions to ask a girl.
3. Is she hard to impress? Bring out your most interesting questions to ask a girl and break through her hard shell.

In Conclusion

Now, you're all set with the best questions to ask a girl over text. You won't have to wonder how to text a girl you like. With all these great questions to ask, it's time to pick up your phone and text the girl that you haven't known how to talk to yet!

These exciting and engaging questions to ask a girl will get you half of the way there. The other half is up to you and your unique personality, so don't be afraid to adjust and improvise these questions as well!

Have you been pondering for ten minutes about what you can write to your crush? Well you have made the right choice and arrived here! In this guide, I am going to give you practical examples of messages you can send to your dream girl through WhatsApp, Facebook Messenger, or any other messaging platform you might use.

Hello, I’m Frankie Caruso and I welcome you to my blog.

The idea of making a guide to help those discover what messages to write (and topics to talk about) to a girl, came from multiple questions that I was asked after I created an article called 10 tips to get a girl on WhatsApp.

Here are some examples:

Steve

Frankie, I like this girl but I don’t know how to start a conversation with her. Please help.

Ted

Frankie, I just started dating this girl and I don’t know what to write. I don’t want to lose her. What questions should I ask?

Donex

I want to have a chat with a girl in my college, but she has no idea who I am. How do I get started?

Nick

What questions can I ask a girl so I don’t look stupid? What questions is she sure to answer? Thanks.

This list could continue for a while…

But I tell you now, Brother I speak the truth! Have you ever asked yourself one of these questions? If you are here, the answer is likely yes.

First off, I want to tell you that you should not feel stupid because you don’t know what the right to a girl. It is actually a very common problem, especially when it is a girl that you really like. It is normal to fear making a mistake.

Unfortunately, in this digital age, knowing what to say to a girl in a chat is pretty fundamental for the earliest stages of dating. Most of the interactions that occur these days happen through chat, SMS, messages, and various social media platforms.

As I stated earlier, I intend to give you practical examples of phrases and messages that you can write to a girl in one of these chats. This will include the very first message, and even step into more complicated correspondence like asking her out.

I simplified this guide by breaking it down into more digestible topics:

• The First Message (Starting the Conversation)
• Best Questions to Ask
• Questions to Get to Know Her Better
• Flirting Messages
• Romantic Messages
• Friendly Messages
• Serious Messages

Ready to get started?

Let’s go!

The First Message (Conversation Starters)

The first message is always the most difficult to send. You don’t get a second chance at a first impression, and the fear of making a mistake or saying something stupid and never getting reply is a significant stress.

But not to worry, as I always say: never miss an opportunity.

So be brave and throw yourself out there.

Within this section, I collected 15 questions that you could ask a girl via text to start a conversation. These are questions I’ve personally tested and know to work % of the time.

Ready to get started? Good.

1 – What’s the best thing that happened to you today?

This is a very good alternative to asking what someone did. It already starts out your conversation on a positive tone.

2 – What’s the scariest situation you’ve ever experienced?

there’s no doubt that everyone has had a situation that has scared them, or some circumstance that made us almost piss our pants. this is a good opportunity to share your experience and hear hers, hopefully starting a longer conversation.

3 – What’s something weird that you find attractive in a person?

Initially, this question might seem pushy, but it isn’t. In fact, many girls find it funny. As well as hoping you find out what she finds attractive, it allows you to get to know her a little better at the same time.

4 – What was your favorite show when you were a kid?

In a way, this is an easy way to segue into your current favorite shows, something that can allow you to find some common ground.

5 – If you could change your life with any celebrity, which would it be?

This actually allows you to do several follow up questions that keeps her engaged in the conversation. Some examples maybe: Would you feel comfortable being stalked by paparazzi? What would you do with all the money?  As you can see, there are many approaches that you could use.

6 – What is the first thing that you would do if you won the lottery?

You will find that a question like this can actually take you on a rather lengthy conversation, but also divulge many of her interests at the same time.

7 – Do you have any favorite songs on Spotify/iTunes/YouTube etc?

You can ask her if she will share them with you or let you listen to some. You might find that there are some things that you both enjoy.

8 – Did you do any after school activities in high school?

Being involved in after school activities can share common interests, and is a way to make connections aside from school.

9 – If you could live anywhere in the world, where would it be?

This gives you an idea of where she sees herself in the future, her current interests, and allows you some very interesting lead-in secondary questions, such as: Japan for its food? Italy for its art? Australia because it has kangaroos?

10 – Do you have a favorite place to have lunch?

You should really pay attention to the answer here, because when you ask her out, you already know someplace that she likes to eat.

11 – What is the craziest thing that you’ve ever eaten?

This is an intriguing question that can open up a lengthier conversation, especially when you both have things to share. You also have the possibility of follow-up questions including what it tasted like, why it was eaten, and if they would do it again.

12 – How frequently would you say you try new things?

Actively search for any new and exciting experiences that help her to grow.

13 – What is the maximum distance that you could reach with a paper plane?

This is a question designed to initially make her laugh. If a girl is laughing, you are on the right track. Challenge her to an airplane race where each contestant gets a dollar bill. Whoever flies the airplane the farthest gets to keep both dollars. It’s a fun little game that puts you in a good light, makes you seem fun, and allows you to spend some physical time with her.

14 – What would you say is the best part about being a woman?

This allows you to inadvertently introduce sex into your conversation.

15 – Do you know any songs by heart?

Listening to a song with somebody is always a nice way to spend some time. Listening to the songs that she knows by heart allows you to get to know her better without being overly pushy.

The Best Questions to Ask the Girl You Like

This section is all about the realest questions. These are foolproof strategies. I won’t lie, at first I didn’t want to share then with anyone, but then I said to myself: why wouldn’t I want to help my readers?

But enough chitchat, let’s get right into the meat…

16 – When was your last pleasurable experience?

Was it her eating a container of Häagen-Dazs ice cream all by herself? Was it the last time she ran through a wheat field? Don’t just have her tell you, have her explain the experience.

17 – Do you have an unexplored secret passion that many people do not know about?

It might be a good door opener to help her follow through on some of her passions. Perhaps she wants to learn how to paint. this might be a good excuse to try one of those “Paint and Wine” evenings at a local establishment. You both get the fun of playing with paint and get a little tipsy on the wine.

18 – Do you prefer group dinners or one on one intimate meetings?

Once you have that answer, you have an open door to ask her to dinner with her friends or to take her out to dinner by herself.

19 – What is the strangest situation that you’ve ever been in?

For your sake, let’s hope she hasn’t seen her parents having sex lol. I’m kidding of course, but it is a good question that can start a long conversation.

20 – Is there a place that you usually go for inspiration? Why is that?

If the girl you like enjoys traveling, hiking, or just taking long walks, this question might just amaze her.

21 – Do you have a favorite seasoning?

You are quickly going to find out if she is somebody that puts ketchup on everything that she eats. Beware.

22 – Do you have a story that you like to tell the most?

We all have a certain story or two that have left the mark on us in a very positive way, or might just be really funny to share. Let her tell you one of those stories, and then respond with your own.

23 – Is there something that he would regret not doing or trying in your life?

There are plenty of things that can end up on a bucket list, including seeing an eclipse, experiencing the Northern Lights, or traveling to Paris. Try to be engaged in her responses to encourage her that anything is possible in her life.

24 – What was the last book that you really liked?

This is a pretty good way to find out if you have similar literary tastes. However, if neither of you is a reader, audiobooks are not too different. I myself listen to audiobooks all the time when I’m making dinner.

25 – If you had to choose one, which of your five senses would you prefer to lose?

You can discuss each of these individually, though some will yield longer conversations than others.

26 – What do you consider your greatest achievement so far? What would you like your greatest accomplishment to be for your whole life?

You might also take the moment to ask her what she’s most proud of. One of the keys to getting a girl and having a positive relationship is supporting their interests and goals. Helping her and encouraging her to achieve these goals makes you a valuable part of her life.

27 – What do you have in your purse right now?

While you should never be the one to go through a woman’s purse, this is a question that can catch her by surprise in a positive way. And, you can learn some of the secrets of her daily life.

28 – Where and when did you see the most beautiful sunset?

Watching the sunset or rise are unique experiences that each of us can remember.

Asking her what the most beautiful sunrise or son said that she’s seen it gives you an image of a hopeless romantic. Girls just love that.

29 – What’s the worst place that you’ve been trapped for a long time?

Airports are in nightmare when your flight gets delayed or canceled, for example. ask her what situations would make her go crazy.

Questions to Get to Know Her Better

Have you gotten past the introductions and know you are ready to get to know her a little better? Have you now become curious about her passions, hobbies, and interests?

It is important to keep the conversation rolling if you broke the ice.

I have put together a list of targeted questions that keep you in a positive light, and keep her talking as well.

And here they are!

30 – What is a cause that you feel close to?

If she is volunteering or devoting her time to something she considers important, it might be something you guys can do together. Talk about a memorable first date for her.

This strategy is great because you get to help out someone or something in need, you meet new people, and it’s a free way to make you look caring and compassionate.

31 – Are there any circumstances where you feel shy?

If you keep this information in mind when you’re with her, you can do more to make her feel comfortable in situations where she would not be. She will realize this as it’s happening and appreciate it.

32 – Is there a special talent or skill that you’ve always wanted to have?

Learning something new can be both challenging and daunting, but it’s a lot easier if somebody is helping you to persevere.

Show that you are willing to help her get started and stick with it.

33 – Which of your family members do you most admire and why?

Let’s have for your sake that she has a family member that she admires at all.

This is a good exploratory question to learn about both her family life and her childhood.

34 – What is your best talent?

You would assume that there is at least one thing that she’s proud of. Ask her what this is, and give her an opportunity to demonstrate.

35 – What made you choose (the current University she is attending)?

This conversation could go in multiple directions, but can give you an idea of her general interests.

36 – What is the most beautiful or traumatic thing that happened to you on a date?

and it’s no great surprise that she likely has a bad history of dating, as you likely do as well. And it’s always good to look back and laugh at times.

37 – Does your family have a strange tradition?

This is a question that can get you a foot in the door about her family life without feeling invasive.

38 – Have you ever had your future predicted by a psychic? If so, what did they tell you?

No matter what you think about fortunetellers or tarot cards, they can be a lot of fun if not taken too seriously. This can also be a chance opening for you to ask her out.

39 – Which event of your teenage years puts you to shame?

better explain some of the stories of these formative years of her life, even bringing out some pictures, and laugh together about your childhood mistakes.

40 – What is the best gift that you’ve ever received?

This is a casual way for you to find out if she prefers experiences or material goods as gifts.

41 – If you could change one thing about yourself, what would it be?

Improving yourself is the key to becoming a better human being. if she is always looking for ways to improve herself, you want to keep her close.

42 – Who was your best friend in elementary school?

We change as we grow, and it’s interesting to see the different paths that we have followed. Have her share with you not only who her best friend was during this time, but why and some of the things that they did.

43 – Do you still follow your friends’ advice?

Some people genuinely learn from their mistakes, while others prefer to follow advice they’ve received. Try to figure out which type of girl she is with this question.

44 – What good do you bring to the group when you hang out with your friends?

This is a question designed to help her see where she fits in with her group of friends. Is she the lonely one? Is she the leader of the group? Is she the fun one? Ask her these type of questions.

45 – Did you follow any specific trends when you were younger?

Introducing some nostalgia into the conversation it was a great way to connect and help her feel closer to you.

46 – What do you think lies in the dark?

This is a probing question because the darkness tends to hide our deepest fears. Find out what monsters haunt her at night.

Sometimes, the monsters aren’t really monsters at all.

47 – What’s your worst habit?

Be sure to share yours too, it is OK to be a little self-critical.

48 – What is something about you that might surprise your parents?

Another great question to make a conversation take a more sexual, hotter turn.

49 – What do you consider to be your weirdest problem?

Asking her about her issues is an ironic way that helps her open up and talk more openly about herself to you.

50 – When you talk about me to other people, what do you say?

Women tell their girlfriends everything – especially about the guys that they’re chatting up and hanging out with. Take a second to make sure that what she’s sharing are all the nice things.

51 – Do you have any nightmares? What happened in them?

This is a great opportunity to turn a serious topic into a joke. If you can make her laugh about things that have made her uncomfortable, you are well on your way to success.

Flirting Messages

As much as it might make you nervous, it’s time to start flirting with the girl that you like.

Pay close attention to the topics that you choose. If you are good at it and you play this situation well, the conversation might take a much hotter turn.

Here are some great topics for flirting with a girl over text.

52 – What is your guilty pleasure?

This is absolutely one of my favorite questions.

It often makes the girl think hard about how to answer. In fact, if she does not have an immediate response you should not worry. Give her time to think about it don’t pressure her with more questions on top of the one.

53 – When was the last time that you stayed up all night?

Everyone at some point in their life has stayed awake all night. Let her tell you about the experience, and if you are skilled, you can direct this conversation towards something hotter.

54 – If I asked you to dress sexy, what would you wear?

Most girls are vain enough to want to talk about themselves constantly. Talking about their outfits and clothes will make her feel more comfortable.

55 – What is the first thing that you look at in a guy?

This helps you to understand what attracts her both physically and intellectually.

56 – How would you define a good sexual relationship?

My definition: a relationship with a LOT of communication, mutual desire to satisfy the other person, and openness. If these things are not present, problems are bound to emerge.

If you tell her this, she is going to fall in love with you.

57 – Would you stay with me if you found out that… I had a criminal record?

If you take a moment to pretend that you’re a serial killer or something equally ridiculous, you’re sure to make her laugh.

58 – Can you describe your idea of a perfect night together?

Take notes here. In the future, you will want to organize this evening exactly how she described it.

59 – When did you lose your virginity? How did that happen?

Your first time is something special. It is OK to look back on it with some tenderness and talk about it with other people. There’s nothing wrong with this conversation even if the experience wasn’t the best.

60 – What do you fantasize about?

Do you have a particular fantasy that you’d like to make come true?

61 – What is the first thing that you would do if you were the opposite sex for one whole day?

Obviously, her answer will be something like swing her penis like a helicopter. Isn’t that what all guys do every morning when they get up?

62 – If you were a ghost for just one day, what is the first thing that you would do?

Basically, this question is more about being given the gift of invisibility. Have her tell you what she would do if she were invisible for a day.

Romantic Questions

Here is a secret that almost everyone knows: girls are into romantic boys. There is a line however. You can get too sappy.

To avoid making this mistake, I prepared some questions that should help you to navigate this conversation in text with the girl that you like.

63 – How important is marriage to you?

Once you find out this you can also ask neighboring questions like the importance of children and family. Do you find out when in her life she hopes to have them.

64 – What do you like most about me?

If she is maintained a chat with you, there’s definitely something that she likes about you. There’s nothing wrong with asking her what her favorite things are when it comes to you.

65 – What can I do to make you understand that I really like you?

Make sure you pay close attention to her answer and never forget to give her some sincere praise for being honest with you.

66 – Is there anything that you would like to tell me?

You can help smooth this over by first sharing something that you’ve never told anyone.

67 – Do you think you still have feelings for someone in your past?

Honestly, you never forget your first love. Don’t get too jealous if she says yes. Talk about it with her. It is actually a great opening to a deep conversation.

68 – What about me is attractive to you?

Perhaps at first, she thought you were a bit silly, but gradually it started to grow into deeper feelings.

69 – If you could change something about me, what would it be?

You need to remember not to take the answer personally. If she is honest enough to share something with you, then you should remember that change is necessary to overall improvement.

70 – How would you define love?

To love is to live. This is a little tip so that you can answer if you find yourself tongue-tied and unable to define it for yourself.

71 – Is there anything in particular that you don’t know about me that you would like to?

There’s probably something she’s been dying to ask you, but she’s been too nervous to do it. Open up now and answer truthfully.

72 – If you are sad or angry, how would you like it to be treated? More specifically, what makes you feel like somebody is actually taking care of you?

You can impress her here by really focusing on her emotions.

73 – What are some of the most truly romantic dates? What are some sexy ones?

Everyone has a different idea of romance. Going to a sex shop and finding new toys is % worth it. Also, I heard the strip club can put you in a good mood for the rest of the night if you’re into that sort of thing.

74 – What gourmet restaurant have you always wanted to try? Do you have a homemade food that you adore?

Spare a bit and surprise her with a couple of dishes that you cannot normally afford or that you’ve never tried. Set up a candlelit dinner for her.

Honestly, you CANNOT go wrong here unless you burn something down.

75 – Do you believe in marriage? Or do you prefer just staying in a serious relationship?

You can learn a lot about the type of girl she is with this question.

Funny Questions

If there is one thing that I have learned in my 30 years, it is that the way to a woman’s heart is through her laughter.

You do not have to be handsome like Brad Pitt. You can be ugly like Chewbacca – you just have to make her laugh.

That’s great advice and all you say, but how can I do that?

Just start sending her nice messages that can put her in a positive mood, like some of these:

76 – What is your favorite video or GIF that makes you laugh?

It is possible that she has already shown you some of her favorite ones by now.

78 – What is your favorite joke?

Q: How much tickling does it take to make an octopus laugh?

A: Tentacles!

Q: Where does a king keep his armies?

A: Up his sleevies!

Silly, stupid – but sure to make her chuckle.

78 – What is the (cutest/most shocking/weirdest/etc.) message you have ever received?

If it was strange enough, she’s probably already got a screenshot of it. Ask her to show it to you.

79 – What is the best picture that you feel you’ve ever taken?

If you need an example, you can always send a picture of her for extra bonus points.

80 – What’s the worst message that you sent by mistake?

Everyone has sent one of these types of messages by mistake.

Allow her to explain this experience and make sure that you don’t miss opportunities to tastefully rib her.

81 – What would you really like to buy right now?

Start this discussion as a playful hypothetical, but try to remember it as something you might consider giving her on your first date.

82 – What is the nicest thing you can buy on the Internet?

For one, there’s a Donald Trump inflatable doll. Imagine her laughing if you tried to give that to her.

83 – What silly phrases do you know for flirting?

“Did it hurt?

What, when I fell from the sky?

No, when you fell down the stairs the other day.”

Now, I told my girlfriend this, and though it was not accepted greatly, we both laughed like idiots. Mission accomplished.

84 – What strange/useless talent do you have?

We all have some talents – some are incredibly useful while others are utterly useless.

Serious Questions

Beyond being funny and likable, you also have to show that you are a deep and serious person as well.

This will keep the girl interested.

I can help you with some interesting topics that you can use during your longer conversations.

85 – What is it that is not real, but you desperately wish would be?

Some examples might be hidden places.

86 – What’s the smell that brings you good memories?

Perfumes and other aromas can take us back in time. What are your favorite scents from your past? Find them and share them so these smells are now connected with you.

87 – What are you best at?

She is likely to have skills of her own and she will appreciate that you’ve taken an interest in them.

88 – What makes you nervous?

For some people it is crowds or absolute silence, but we all have something that makes us uncomfortable. Ask her how you can help her feel more comfortable when she gets nervous.

89 – Are there needs in your life that have not been fulfilled? Is there anything I can do to help you?

Every one of us has different needs. If it is OK with her, help her with what she needs. If she likes you, she will want to do the same. Just don’t be clingy.

So far, I have shown you questions for the girl that you like. But what if you’re already dating this girl?

I have been thinking a lot about that too, so I decided to select some questions that you can ask to keep the conversation going with your girlfriend. As usual, you can copy and paste them into whatever messaging app that you use to chat with her.

90 – If you could change one thing about yourself, what would it be?

If it is something about herself that she can change, offer your help in creating a plan and putting it into action.

91 – Did you feel closer to your mom or your dad when you were growing up?

Our parents always have a favorite child, so naturally, we can have a favorite parent too.

92 – Who do you trust the most?

This might divulge who your girlfriend’s best friend in the world is.

93 – Have you ever left someone you still love?

There are many instances that you have to leave a relationship because it is unhealthy.

Be as nice as you can be, and hope that she does not have to do this to you.

94 – When was the last time you were really disappointed?

Have you been in a bad mood lately? Has the moment passed or is there something I can still do to help?

95 – When was the last time that you failed at something?

Be understanding and work hard to find a positive aspect of the story.

96 – What is it that always makes you smile?

What is a consistent something that always brightens your day.

97 – If you could up and change jobs without worrying about money, what would you rather be doing?

It does not have to be some crazy change. You can always keep you day job and devote some of your free time to your passions. For example, like I do with my blog.

98 – Which of your past relationships have made you happiest? Why did they end?

Many people might tell you it’s a bad idea to talk about someone’s exes. I disagree. You can learn a lot from the most things her exes made and not make them yourself.

99 – Have you ever forgiven yourself for bad things that you did?

Everyone is done something that they regret. We have to forgive ourselves if we want to move on and lead happier lives.

– In the ideal intimate relationship? How often would you have sexual relations?

Communicate your own needs and find the happy medium you both can agree on.

Bonus: Starting a Conversation with the Girl You Like: 4 Great Tips

In recent years, I’ve had the chance to have many long talks with you on my Instagram profile. (@carusino – follow me if you like!)

I have found that there are fears common to everyone approaching a girl for the first time. You might fear not knowing how to manage the situation, a fear of being dumped, or a fear of not knowing what to say.

That is why I have decided as a bonus to throw out these 4 tips:

Tip #1: Relax

If she is texting you back, some part of her is attracted to you. It is easy to give loss the negative thoughts. Instead, let things happen naturally.

Tip #2: Listen

Really pay attention and don’t forget what she says. Girls like to tell their feelings, how they spent their day, etc. If you really like her, she deserves your full attention.

Tip #3: Ask the Right Questions

I might have already provided you with a virtually endless list of questions here, but you should take the opportunity to probe each of these more deeply. Show her that you’re really listening and are interested in what she has to say.

Tip #4: Be Yourself and Try to Have Fun

You know you don’t want to lose her. If you are hiding your real self, she’s going to find that out eventually.

Conclusion

OK, we have finally come to the end of this gigantic guide.

I’m not going to hide that I’ve worked a long time on it, and that it has not been easy to put together. In the end I am happy because I know this will help you.

Before we say goodbye, let me briefly recap the types of questions that you can find on this list.

First, I have included several icebreaking phrases. I would consider these the first messages you would send to a girl that you like.

I then put together the best 20 questions that you can ask a girl that makes a good first impression.

And the third part, you find a section devoted to personal questions to help you get to know the girl better. These help you gain her trust.

In the fourth part, I picked 10 questions devoted exclusively to flirting. Flirting with a girl is very important because that is the direct way to show her you’re interested.

The fifth section shows you some romantic questions. These are the questions you can ask if you’ve already dated her (or started dating her recently), or if you have not had the chance yet. Girls enjoy seeing a romantic side.

Sections six and seven are dedicated to fun and serious topics that keep the conversation going.

Finally, I took a moment to give you 4 tips that should help you through this whole process:

• Relax
• Listen
• Ask the Right Questions
• Be Yourself

That’s really it.

Come back and see me – I will anxiously await some feedback on how these questions worked for you.

A big hug (and a bit of luck),

PS – Here are some tips to bring the conversation out of messaging apps and get a real date.

About Frankie Caruso

Starting the conversation off right is often the toughest struggle when texting the girl you fancy. The following are some texting conversation starters that should steer you in the right direction.

The key to starting a lasting conversation is to keep your questions open-ended. Make her reply with more than yes or no.

These texts will pique her interest and set you up for engaging conversation.

20 Conversation Starters To Ask A Girl Over Text

1. What are your plans for this weekend?
2. What was the highlight of your day?
3. What’s your schedule like today?
4. Did you watch the last episode of (relevant TV show)?
5. What did you eat today?
6. What is something funny that happened to you today? [1]
7. Are you going to (party, bar, etc.) this weekend?
8. Working on anything exciting?
9. What was the highlight of your week?
10. Having fun?
11. Have you been to (restaurant, store, etc.) yet?
12. What’s your new year&#;s resolution?
13. Are you going home for the holidays?
14. What’s your ideal Sunday?
15. Where do you want to be right now?
16. Would you rather go out for sushi or for pizza?
17. When can I see you again?
18. Looking for an adventure?
19. When are you free?
20. What three things would you bring on a desert island?

20 Funny Questions to Ask a Girl Over Text

1. What did you ask santa for last christmas?
2. What’s your greatest fashion disaster? [2]
3. Are you tired from running through my dreams last night?
4. You’ve heard of Netflix and chill, but have you heard of Disney plus and Thrust.
5. I think your hotness might be the cause of global warming.
6. You’re making my face hurt from smiling all the time.
7. Stop sending mixed signals and send memes instead.
8. Would you rather be abducted by aliens or go out with me?
9. If I could rearrange the alphabet, I&#;d put U and I together.
10. God was feeling himself when he made you.
11. I got you some flowers! (send flower emojis)
12. You’re like a tornado… you blow me away.
13. I’m using my last 3% to text you right now
14. So.. I have this big problem. I can’t stop thinking about you.
15. Do your parents like to bake? Because they made a cutie pie.
16. How do you like your eggs? Scrambled or fertilized?
17. I hope you see my willingness to text first as attractive.
18. Here I am, the guy of your dreams.
19. You’re my favorite distraction.
20. Fuck, Marry, Kill with Guy Fieri, Peter Dinklage, and Danny Devito. What are your choices?

Recommended: 82 Dark Humor Jokes

20 Get to Know Her Questions to Ask a Girl Over Text

1. Where’s your hometown?
2. Do you have siblings?
3. Where are the places you want to live/ see?
4. Where’s the coolest place you’ve been?
5. A genie gives you a wish. What do you wish for?
6. Do you prefer a night out or a night in?
7. What were you into as a kid?
8. What’s on your bucket list?
9. What’s your favorite movie?
10. What was your favorite movie as a kid?
11. What’s your favorite song?
12. Who are your favorite artists?
13. What’s your favorite TV show?
14. What do you think about tattoos? [3]
15. What are you obsessed with?
16. Do you sing outside of the shower?
17. What’s your go-to dirty joke?
18. If you were only allowed to eat one thing for the rest of your life what would that be?
19. What is something you did once and will never do again?
20. What are your favorite things to do in your free time?

20 Flirty Questions to Ask a Girl Over Text

1. What would you do if I was with you right now?
2. I don’t remember the last time we spoke, let&#;s change that.
3. Did you smile when I texted you just now?
4. What are you wearing right now?
5. I wish I woke up to your smile this morning.
6. I’m just trying to get to the part when we’re eating pizza in your bed in our underwear.
7. What are you doing tonight? Let&#;s get brunch in the morning
8. Has anyone told you that you look stunning today?
9. Wish I could kiss you right now.
10. Include me in your “to-do” list today.
11. It’s chilly out… come warm me up
12. What would you ask if you knew the answer was “yes.”
13. Missing me?
14. You were in my dreams last night; I didn’t want to wake up.
15. Out of all of your sexy curves, your smile is my favorite.
16. I’m jealous of your bedsheets.
17. Can I have you for my midnight snack?
18. Don’t work too hard today. I need you to have energy later.
19. Facetime me. I need your smile to brighten my day.
20. Just say the word, and I’m by your side.

Recommended: 20 Topics To Talk About With A Girl

20 Personal / Deep Questions to Ask a Girl Over Text

1. What’s your relationship like with your mom?
2. What’s your relationship like with your dad?
3. What excites you most?
4. What’s a good day for you?
5. What is your most embarrassing moment?
6. Who brings you the most joy in your life?
7. Where would you want to start your family?
8. What book changed your life?
9. Who are the biggest influences on who you are?
10. What’s your defining moment?
11. What keeps you up at night?
12. When was your first time?
13. What’s the thing you most want to tell me?
14. Send me your favorite selfie on your phone.
15. What songs do you want me to listen to?
16. What’s your most irrational fear? [4]
17. What would make your day, right now?
18. What are your biggest turn-ons?
19. What are your biggest turn-offs?
20. What do you notice in a guy first?

Dating for Guys :

How to Talk to Girls Online &#; What REALLY Works
How To Tell If A Girl Likes You Over Text 
How to Ask a Girl Out over Text
20 Topics To Talk About With A Girl
21 Questions To Ask a Girl
50 Great Compliments for Girls