44 Interesting Questions To Ask a Guy You’re Crushing On

couple discussing questions at cafe

The butterflies that come with a new crush can be exhilarating. You’re in the first blush of what could be love, and you want to learn everything you can about him. What’s his favorite color? Does he like pets? Where does he see himself in 10 years? These questions will help you learn more about your new guy, but if you’re looking to dig deeper, here are 44 Interesting questions to ask a guy you’re crushing on.

You don’t need to be tongue-tied when chatting with your date. There are many different questions to ask a guy that’ll help you both feel more comfortable. So, keep these in your back pocket the next time you’re looking for interesting questions to ask to keep the conversation flowing and the good times going.

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What Are Interesting Questions to Ask a Guy?

After the first date, you’ve likely covered many of the fundamental good questions. You know what he does, what some of his favorite hobbies are, and maybe even a little bit about his family life. Now, you want to keep the conversation going on date night. You’re trying to keep his interest, so you’ll want to start asking more profound questions, listening, and following up with new questions based on his answers.

Interesting questions to ask a guy can be fun and quirky, like, if you were an animal, which would you be and why? Or they can be more serious, hinting at their future aspirations and past experiences. No matter how you’re approaching questions to ask a guy, pay attention to what he’s saying and ask thoughtful follow-up questions. Listen more than you talk. You’ll get to know so much more about the guy you’re crushing on during small talk.

If you find any of the answers troubling, you’ll want to dig deeper without prying too much to understand the why behind the answer. It could be that you’re not compatible on specific personality issues, but you agree to disagree. In some cases, you’ll find that your values don’t align. If this is the case, don’t try to force it. Neither of you can change your fundamental truth, so you’ll have to learn to agree to disagree or move on.

Interesting Questions to Ask a Guy

It may be hard to know exactly where to start a conversation, but there are great questions for every scenario. Whether you’re looking for fun, flirty, or juicy questions, here are 44 questions to ask a guy.

Flirty questions

You’re on a date, so it’s clear you’re into each other, but how much? Fun, flirty questions can help you keep the spark going, and make sure to lean in, touch, and laugh at your crush’s jokes to encourage your date. Dating can be tricky, so these extra cues will help you both feel more comfortable.

1) What Was The First Thing You Noticed About Me?

Interesting questions to ask can include things about you but cover other questions too. When he answers, offer what attracted you to him, so you’re even.

2) What’s The One Trait That Can Make Someone Irresistible?

Keep this answer in your back pocket for the next date! If it’s something you can do, say, or wear, he’ll notice you paid attention.

3) What’s The Craziest Thing That You’ve Ever Done?

Spontaneity can be fun! Questions to ask a guy like these can see if you’re compatible. After all, if he stole a cop car when he was drunk, and all you’ve done is returned a library book late, you may not be on the same level.

4) What Body Part Are You Most Proud Of and Why?

Everyone has one feature they’re most proud of on their body. Some will say their eyes, lips, or even their arms if they’re working out.

5) What’s the Best Kiss You’ve Ever Had, and How Can We Top It?

Let your competitive nature shine with this question, which will help you see where the past stands and how you can top it.

6) What Are The Best Ways to Make You Smile?

How to make your crush happy early on will only benefit you in the long run!

7) What’s Your Biggest Turn-On?

Be as safe or kinky as you like with questions to ask a guy. If you want to be extra flirty, lean into his answer, touch your shirt to draw attention to your cleavage, and say, “I can see why” in a husky voice. He’ll eat it up.

8) What Do You Look For in a Partner?

Interesting questions to ask will get you more information about your partner as a person, so, questions to ask a guy like these can help you see if you have core traits that you’re each looking for in a relationship.

9) Have You Ever Been in Love?

Maybe the most invasive flirty question to ask a guy, but you can tone it down by joking afterward, “Do you want to be?” It’s good to know what the starting line is when your crushing. If they’re still hung up on their ex, and you want something more serious, it’s better to know sooner than later.

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Funny Questions

Funny questions are a great way to lighten the mood and see if you have similar senses of humor. They can be general questions to help to break any awkwardness, so make sure to have some fun questions ready to go.

10) What’s The Best Pick-Pp Line You’ve Ever Used or Worked on You?

You can tell a lot about someone based on what type of lines work on them. Do they prefer charm or humor? Are they into more direct approaches? You can learn how to interact through these interesting questions to ask.

11) What’s The Most Embarrassing Thing That’s Happened to You?

Don’t ask this question if your date takes themselves too seriously. They’ll likely clam up. Your date has to be okay with laughing at themselves to answer this one and confident enough to share stories that won’t paint them in the best light.

12) If You Suddenly Turned Invisible, What Would You Do?

Encourage your crush to be honest, no matter how bad it may be. It’s one of the cute, PG, interesting questions to ask.

13) Who Was Your Celebrity Crush Growing Up? Has Your Type Changed?

We all had embarrassing crushes as a kid – sometimes our type stays the same while other times it drastically changes.

14) If You Were in a TV Show, Which One and What Character Would You Be?

Bonus points because you’ll get to see if your TV watching tastes are compatible, and if you don’t know the show he references, you can always promise to watch and report back.

15) What’s Your Go-To Karaoke Song?

They sing this song at the top of their lungs in the shower, in the car, or wherever. You’ll learn more about his music taste with these questions to ask a guy.

16) If Your Life Was a Movie, What Would be its Title?

Like TV, questions to ask a guy like this can tell you more about his movie tastes and if they will gel with yours.

17) What’s The One Thing Guaranteed to Make You Laugh?

We all have a comfort show, video, song, or something else that can put a smile on our face no matter how bad our day is. Interesting questions to ask a guy can help you learn more and be the person who makes him smile.

Intimate Questions

Sexy questions can help you understand if you and your crush are sexually compatible right off the bat. They’re a fun way to take the dirty talk up another notch if you’re both ready to take it to the next level.

18) Is There Anything You’ve Always Wanted to Try Sexually but Never Have?

Be prepared to follow up and ask if he’d finally like to try if you’re at that point in the relationship.

19) When Did You Lose Your Virginity?

A highly personal question, but you can bond over your sexual experiences with similar questions to ask a guy.

20) What’s Your Favorite Type of Lingerie?

Afterward, ask if he’d like to see you in it, grabbing his hand and lightly stroking his wrist suggestively.

21) What’s The Biggest Sexual Fantasy You Have?

It may take some time for your crush to open up about this, so expect the answer to change from the beginning of a relationship to when you’re more well established.

22) Are You a Top or a Bottom?

You can learn if your partner is dominant or submissive by asking this question.

23) What’s The Best Time of Day For Sex?

Do your cycles sync? Or is the best time of day for sex anytime?

24) What’s Your Favorite Sexual Position?

If you haven’t heard of it, ask if you can try it out next time you’re in bed.

25) What’s Your Favorite Thing To Do to a Partner?

Tell them how much you loved it if your crush has already tried it on you. If not, tell them you can’t wait! Interesting questions to ask a guy can always open the door to more fun times!

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Thoughtful Questions

Deep questions delve beyond the surface, and they’re great to ask on a second date when you’re past the basic, topical questions. They’re interesting questions to ask, though you’ll want to make sure you’re not being too nosy. You don’t want to come off too strong as you think about different questions to ask a guy.

26) What’s The One Thing You Can Talk About Forever?

You’ll get a deep dive into his interests when you ask this question.

27) Who’s Your Biggest Role Model?

You’ll learn more about who helped shape your crush into the person they are today when you consider this and other questions to ask a guy.

28) How Did You Get Into Your Career?

You may have talked about his degree already, but what path did he take to get him where he is today?

29) We All Have Goals. What’s The Next Thing You’re Hoping to Accomplish?

It can be big or small but knowing that he has plans can help put your mind at ease that progress is in his future.

30) If You Knew Your Future, Would You Try to Change It or Accept The Journey?

This can hint at his approach to life when you consider interesting questions to ask. If he has control issues, he’ll try to impact every detail.

31) What Would You Like Your Legacy To Be?

We all hope to leave something behind, whether it’s a financial legacy or children. What he wants to be remembered for can tell you how he lives his life.

32) What Scares You?

This may be too deep at the beginning of a relationship, but learning your crush’s fears can help you understand what drives him.

33) What Are The Most Important Lessons You’ve Learned From Your Parents? What’s The Most Useful Thing You Learned? Are There Any Things That You Learned Not To Do?

We learn a lot from our families, including how to have relationships. It’s interesting to know how a guy thinks about his family, and what important lessons he’s learned throughout life.

Random Questions

Random questions can be anything that comes to mind during the date or scripted in advance. You’ll spark fun and spontaneous conversation when you consider random questions to ask a guy.

34) Suddenly, You Find Yourself in Witness Protection. What’s Your New Persona and Why?

Better yet, what did they do to land themselves in trouble? What interesting questions to ask a guy when you’re getting to know him!

35) Introverted or Extroverted?

Opposites attract, but it’s important to know how you get your energy and how you like to recharge.

36) You Won the Lottery and Have All the Money You Dreamed Of. What’s The First Thing You’re Doing? Why?

How he answers this question can tell you if he’s practical or a dreamer, as well as a little more about his spending habits.

37) What’s a Conspiracy Theory That You Believe In?

This could be a fun question or one that sends you running for the hills, but it’s better to know from the start if his views are a little out of this world. We fully support believing in extraterrestrial life, but the tinfoil hat could be a bit much. 

38) If You Had to Set a Personal Motto, What Would It Be and Why?

Give him time to think if he doesn’t know one off the top of his head. Not everyone has words they live by on the ready.

39) What’s The Most Trouble You’ve Ever Been In?

Like what’s the craziest thing you’ve done, how much trouble they’ve ever been in could help you understand if he’s a boyscout, rule breaker, or lives as if rules don’t apply to him.

40) What’s Your Least Favorite Food?

You likely covered his favorite food already, but what’s the food he can’t stand?

41) What Artist or Band Would You See In a Perfect World? They Can be Dead, Alive, Broken Up, or Still Together – We’re Talking Wishlists Here!

Music taste, like movies and TV, is a fun conversation starter. Plus, you’d rather know if he’s into dad rock now and not later when he’s serenading you with Pearl Jam in the shower. 

42) Coke or Pepsi?

You have to know what to mix in your drinks!

43) Beer or Wine?

You’ll want to keep the fridge (or counter) stocked with the right type of drink.

44) If You Could Live In a Book, Which One and Why?

Not everyone’s a reader, so don’t judge too harshly if he chooses a book he read in high school. Although, if he chooses 1984 or Brave New World, concern might be valid. 

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The Best Way to Ask Your Questions

In the beginning, you don’t want to feel like you’re being too nosey when thinking about conversation starters, and if you’ve done some prior research, you don’t want to give yourself away and come off too much like a stalker. Here’s the best way to ask your questions to get your desired results. In most cases, you’ll just be looking to learn more about your crush, but it can also lead to some interesting discussion points as the date goes on. Just remember to keep your questions fun and light in the beginning.

Don’t Ask Rapid Fire Questions

Just because we’ve provided you with 44 questions doesn’t mean that you have to ask them all, so take a deep breath, pick a handful of your favorites, and keep them on the ready in your back pocket in case of an emergency.

If you fire them off, it’ll seem more like a job interview and less like a date. Your date won’t have time to think about their answer, and you’ll only get surface-level responses that don’t give you much to go on. It’s natural to be nervous, but when thinking about questions to ask a guy, quality is way more important than quantity.

Don’t Dig Too Deep

Early on in a relationship is not the time to be discussing emotional trauma or baggage you have from old relationships, so avoid these topics when thinking about questions to ask a guy. Once you’re more settled in your relationship, you can broach these. These are interesting questions to ask, but you may cross a line that you aren’t aware of if you ask them too soon.

Also, if you’re curious about something you uncovered while doing some preliminary internet stalking, weave it into conversation naturally. You don’t want to give yourself away by referencing specific social media posts or newspaper records.

Be Confident

You have a lot to offer on any date, so own it! Be confident. Don’t apologize for asking questions that are important to you, though you also need to respect if your crush isn’t ready to pour their heart out to you just yet. When choosing questions to ask a guy, pick a mix of serious, fun, sexy, and silly. You can’t go wrong with that combination!

It’s okay to be curious, and interesting questions to ask your date can be a great way to get more information about your compatibility. Own what you’re asking, no matter how invasive or weird it can be!

Always Listen More Than You Talk

After you select what questions to ask a guy, remember to listen. It’s just as important to listen to what they say as it is to ask the question itself. Show genuine interest and ask follow-up questions as needed based on the answer. When you choose questions to ask a guy, it’ll often uncover even more interesting questions to ask.

Don’t listen to talk either. It can be tempting to relate all answers to you to show you have a lot in common but resist the urge. You’ll come across as self-centered if you always steer the conversation back to you. It’s better to let your date do most of the talking because that’s how you’ll earn more about them.

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Don’t Get Upset

As you pick which questions to ask a guy, you may hear responses that you don’t like. You and your crush don’t have to agree on every point, so take a deep breath before you jump into a heated discussion. Instead, consider if the issue is important to you.

Religion and politics can be integral to our sense of self, but if your crush is a Coke person and you prefer Pepsi, you don’t have to lecture on the merits of one over the other. Instead, accept that you’re different and identify if it’s something you can live with without driving you crazy. If not, it’s time to cut your losses before you get in too deep.

Questions to ask a guy can help you identify if you’re compatible with your crush, so keep thinking of interesting questions to ask.

The Final Say on Questions to Ask a Guy

No question is off the table if you’re brave enough, but if you’re looking to keep it light, fun, and sexy, consider interesting questions to ask over serious ones. You can keep the spark and flirtiness going without being haunted by the ghosts of relationships past.

Be confident without being pushy when considering questions to ask a guy. You may feel nervous, but don’t rattle off questions lest you risk chasing your date off with your intensity. Listen more than you talk, and follow up with thoughtful questions to show you were engaged in the conversation. It can be difficult but try not to steer the conversation back to you. In your quest to be relatable, you’ll look self-centered and selfish.

Lastly, don’t get upset. Our differences make us unique, so there are bound to be issues that you and your partner disagree with fundamentally. That’s why questions to ask a guy are so important. They help you uncover what dealbreakers are, areas you’ll agree to disagree with, and what you shouldn’t talk about to avoid a fight.

Questions to ask a guy you’re crushing on should be fun and topical, digging deeper with each subsequent date. It takes time to get to know your partner properly, and these 44 interesting questions to ask a guy are just the beginning!

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