350 Questions to Ask a Guy They’ll Actually Like Answering

Find all of Teen Vogue's questions & games stories here.

Getting a conversation going can be tough. But if you’re looking for questions to ask a guy, don’t overthink it. What matters most isn’t gender — it’s what you want out of the moment!

Maybe you’re fishing for flirty questions to ask your crush while texting. Maybe you’re looking for personal questions to ask a guy friend, to take the friendship a little bit deeper. Or maybe you’re just killing time and need something to ask your bestie’s older brother before things get awkward. Whatever gabbing-with-guys situation you’re in, we’ve rounded up more good questions than you’ll probably have time to ask. (But if we’re wrong and you make it through ‘em all, you can always pull from our list of questions to ask a girl or our fave questions to get to know someone!)

Think of this list as your conversation-starter starter pack, full of questions to ask a guy on a first date when nerves kick in, good questions to ask your boyfriend when you’re already official, and silly-to-deep questions to ask a guy friend you want to know better. Having a few go-tos ready will make the whole convo way less stressful — and a lot more fun. Eventually (hopefully!) things will start to flow after a thoughtful planted question or three. But if they don’t, don’t stress too much — because we’ve put together plenty of questions across topics and vibes below to keep things moving.

Ahead, check out our favorite questions to ask a guy (or honestly, anyone you want to know better).

In this article, find:

• Spicy & Flirty Questions to Ask a Guy
• Questions to Ask a Guy Over Text
• Funny Questions to Ask a Guy
• Personal Questions to Ask a Guy
• Random Questions to Ask a Guy
• Questions to Ask a Guy You Like (Before Dating)
• Romantic Questions to Ask a Guy
• Deep Questions to Ask Your Boyfriend

1. What’s your love language?
2. Do you have a go-to pick-up line?
3. What’s your flirt style?
4. What’s the most confident thing someone’s ever done to flirt with you?
5. What do you find the most attractive about other people?
6. What’s your idea of the perfect date?
7. Have you ever had a crush on someone you really shouldn’t have?
8. Do you ever make the first move?
9. How do you act when you're really into someone?
10. If I were a flower, what kind of flower would I be?
11. What do you like most about me?
12. How do you know you really like someone?
13. Do you consider yourself romantic?
14. What’s your take on “the thrill of the almost”?
15. When is the last time you felt butterflies?
16. What's something subtle that instantly turns you on?
17. What’s the worst pick-up line?
18. What’s the longest relationship you’ve ever had?
19. Do you have a type?
20. How do you feel about public displays of affection—hand-holding, quick kisses, arm around me?
21. What do you most often think about before you fall asleep?
22. What’s your ideal night in?
23. How do you most like to be flirted with?
24. What would our first date look like?
25. Who was your first crush?
26. What are you like as a boyfriend?
27. What’s your weakness when it comes to attraction?
28. What’s your best relationship advice?
29. Would you rather give or receive a gift?
30. What’s the perfect way to ask someone out?
31. Do you like a slow burn or love-at-first-sight energy?
32. What’s something you’ve always wanted someone to whisper in your ear?
33. What’s something you wear when you want to feel extra attractive?
34. Do you like the chase or being chased?
35. What’s your biggest dealbreaker when you’re on a date?
36. What’s the boldest thing someone’s ever said to you — and did it work?
37. If we were stuck in an elevator, what would happen?
38. Have you ever had a moment where the tension was so strong it felt like a movie scene?
39. Do you believe in soul mates?
40. Do you think mystery is hot, or do you like when someone lays it all out?
41. What’s a pet name you secretly like (even if you’d never admit it)?
42. When are you going to ask me out?

1. How was your day?
2. Do you have a favorite genre of movies?
3. If you could listen to any song on repeat for a week straight, which would you choose?
4. Would you rather be a rock star or a movie star?
5. If you had three wishes, what would they be?
6. Do you have a go-to recipe?
7. Do you prefer cats or dogs?
8. What are you thinking about right now?
9. What’s something you’ve done recently that you’re really proud of?
10. How would your best friend describe you?
11. What’s the weirdest thing that’s happening to you this week?
12. What was the best vacation you’ve ever taken?
13. What emoji makes you think of me?
14. What would be on a playlist you make for me?
15. How would you describe yourself in three words?
16. How would you describe me in three words?
17. What’s your favorite Wikipedia page?
18. What do your weekends look like, and how do I fit into them?
19. How do you describe me to your friends?
20. What unnecessary products do you deem necessary to your life?
21. Guess what emoji I put next to your name right now on my phone?
22. What’s the most useless advice you’ve ever gotten?
23. What’s something you’ve always wanted to ask me?
24. Would you ever stay friends with an ex?
25. What are your five most frequently used emojis?
26. Do you prefer texts or calls?
27. What do you wish you had more time for?
28. What would you make me for dinner?
29. What kind of conversations do you enjoy the most?
30. When do you feel the happiest?

1. If you could switch bodies with the president or your favorite actor, which would you choose?
2. If you could be an airplane or a train, which would you choose?
3. What’s the worst text you’ve accidentally sent?
4. Who is your favorite comedian?
5. Is cereal soup?
6. Is a hot dog a sandwich?
7. What kind of secret society would you start?
8. What’s the most embarrassing thing in your closet?
9. What inanimate object would you delete from existence?
10. What’s the funniest nickname you’ve ever been given?
11. What would be the worst “buy one, get one” sale item of all time?
12. What would three of your cheat codes be if life was a video game?
13. Do you know anyone who reminds you of a cartoon character?
14. What’s the best inside joke you’ve ever been a part of?
15. If all animals could talk, which one do you think would be the rudest? How about the funniest?
16. Would you rather sneeze or fart loudly every hour?
17. What do you think the best WiFi name is?
18. Do you judge people for putting pineapple on pizza?
19. What’s the most useless invention of all time?
20. Which instrument do you find the most annoying?
21. What’s the most obnoxious color?
22. What’s an invisible thing you wish humans could see?
23. What’s the weirdest thing you’ve ever smelled?
24. What movie would be much better as a musical?
25. What’s one thing everyone looks stupid doing?
26. What three items would you buy together at a grocery store to make a cashier laugh?
27. What’s the best type of cheese?
28. What’s the oddest thing you’ve seen in someone else’s home?
29. What’s the funniest insult you can come up with on the spot?
30. What mythical creature do you wish was real?

1. What’s your biggest fear?
2. What makes you feel comfortable around a person?
3. Where do you feel the safest?
4. What’s your favorite childhood memory?
5. Is there anything you would change about your childhood?
6. What did your childhood bedroom look like?
7. What’s the nicest thing anyone has ever done for you?
8. What do you see yourself doing in five years?
9. What’s the biggest life lesson you’ve learned so far?
10. Who is your biggest role model?
11. Have you ever read a book that changed your life?
12. What makes you feel the most confident?
13. Are you close to your parents?
14. Do you think you would be a good parent someday?
15. What’s your biggest regret?
16. Do you consider yourself an introvert or an extrovert?
17. What are you most thankful for?
18. What’s on your bucket list?
19. What are you most passionate about?
20. How do you hope people remember you?
21. What makes you emotional?
22. What’s been your highest point in life so far? What about the lowest?
23. What do you think your best quality is?
24. What is one thing you would change about yourself?
25. Have you ever lost someone close to you?
26. Are you good at giving advice?
27. What puts you in a good mood?
28. Are you a spiritual person?
29. What isn’t real that you desperately wish was?
30. What’s the biggest lie you’ve ever told?
31. What’s the biggest compliment someone has ever given you?
32. Which is more important: love or money?
33. What does self-love look like in your actual day-to-day life?
34. What’s something you're still learning how to say out loud?
35. How do you recharge when life feels overwhelming?

1. What would your chosen super power be?
2. If you could be any insect, which one would you choose?
3. If you could only wear one color for the rest of your life, which one would it be?
4. Are you a night owl or an early bird?
5. Do you often dream while you sleep?
6. How would you spend one million dollars?
7. What does your dream house look like?
8. If you could be a professional in any sport, which would you choose?
9. What are your favorite things to do on the weekend?
10. What’s your go-to joke?
11. What movie makes you feel better whenever you watch it?
12. Are there any holiday traditions you wish your family practiced?
13. If you could travel forward in time or backward in time, which would you choose?
14. You can attend a concert by any musician alive or dead — who do you choose and where is the concert?
15. If money weren’t an issue, what would your dream job be?
16. Sweaty or cold — which is worse?
17. Would you rather have a month-long staycation or a week-long adventure?
18. If you could trade places with any Marvel character, which one would you choose?
19. Ice cream every night for a month or the best pizza in the world every week for a year?
20. Sneakers or sandals?
21. If you could meet any one of your heroes, which one would you choose?
22. Would you rather write a bestselling book or paint a famous piece of artwork?
23. If you could plan the perfect day, what would be on the itinerary?
24. Group trips or solo trips?
25. Driver’s seat or passenger seat?
26. What’s a condiment that makes every food better?
27. What’s your picture-perfect breakfast?
28. Who would narrate a book about your life?
29. What would your villain origin story be?
30. If your life had a laugh track, when would it go off the most?
31. What’s your zombie apocalypse survival plan — and do you actually think it would work?
32. What would be your signature scent if you were a candle?
33. What’s a conspiracy theory you don’t believe in, but kind of wish were true?
34. What’s your favorite completely useless fact?
35. If animals had political systems, which species would rule the world?
36. What’s a word you irrationally hate?
37. If you could only communicate using movie quotes for a day, which movie are you choosing?
38. What’s something you’re 100% terrible at but still enjoy doing?
39. If your brain had a theme song, what would it be?
40. What cartoon character do you relate to way too much?
41. What’s the weirdest compliment you’ve ever received?
42. What’s your go-to weird flex?
43. If you had to wear one Halloween costume every day for a year, what would it be?
44. What animal would you least want to be reincarnated as?
45. What fictional universe would you thrive in?
46. What’s a totally normal thing that freaks you out a little?
47. If your dreams were broadcast like a TV show, would you let people tune in?
48. What smell do you weirdly love that most people probably don’t?
49. If you could invent a new holiday, what would it celebrate?
50. What’s your signature chaotic habit that your friends totally expect from you?

1. What’s the first thing you noticed about me that made you want to keep talking?
2. How do you usually act when you’re into someone — cool and chill, or nervous and obvious?
3. If we had met in a movie, what kind of scene would it have been?
4. What’s one thing you wish I’d ask you, but I haven’t yet?
5. When did you first realize we had chemistry?
6. What’s something you’re dying to know about me, but haven’t asked?
7. What do you think we’d be like as a team — chaotic good or power couple energy?
8. What’s your favorite kind of flirting — playful, deep, or bold?
9. Is there a moment between us you keep replaying in your head?
10. How do you usually show someone that you’re into them?
11. Do you believe in “right person, wrong time,” or is that just an excuse?
12. What’s one thing you find adorable about me that I probably don’t realize?
13. What kind of couple would we be in an alternate universe?
14. What’s something small I’ve done that made a big impression on you?
15. If we had a shared playlist, what would the first song be?
16. How do you picture our first official date going?
17. What do you think our zodiac signs say about us?
18. If I challenged you to a spontaneous adventure, would you say yes?
19. What’s your go-to move when you’re trying to win someone over?
20. What’s something that makes you instantly more attracted to someone?
21. Would you rather have a deep late-night convo or a spontaneous daytime hangout?
22. Do you think we’d survive a road trip together—and who’s in charge of the playlist?
23. What’s your ideal version of “quality time” with someone you like?
24. When you think about crushes, what makes one turn into something more?
25. What’s one compliment you wish people gave you more often?
26. If I told you I had a dream about you, what would you guess it was about?
27. Have you ever started liking someone totally unexpectedly—and did it work out?
28. What’s your opinion on mixed signals—are they ever worth decoding?
29. What’s your biggest hint that you're catching feelings?
30. If we were in a TV show, what would be our couple nickname?
31. What’s your idea of a healthy disagreement in a relationship?
32. How do you usually handle stress when it affects your partner?
33. What’s one thing you think every couple should talk about early on?
34. How do you balance independence and togetherness in a relationship?
35. What’s a relationship habit you think is underrated but important?
36. How do you show support when someone you care about is struggling?
37. What’s your love language, and how do you like to receive it?
38. What’s one thing that instantly builds trust for you?
39. Have you ever had a relationship that surprised you? How so?
40. How do you know when it’s time to talk about something serious?
41. How do you handle jealousy or insecurity in a relationship?
42. What’s your go-to way to make up after a fight?
43. What’s something you think people often overlook when it comes to communication?
44. How do you like to keep the spark alive over time?
45. What’s a dealbreaker for you that might surprise people?
46. How do you like to show appreciation in a relationship?
47. How important is humor to you in a relationship?
48. What’s your favorite way to spend a quiet night with someone you care about?
49. How do you handle differences in opinions or values with a partner?
50. What’s your perspective on forgiveness in relationships?
51. What’s something small that means a lot to you in a relationship?
52. How do you think past heartbreak shapes the way we love?
53. What’s the best compliment you’ve ever gotten from a partner?
54. How do you balance being honest while also being kind?
55. What’s one thing you hope people remember about you as a partner?
56. What’s one thing you’ve learned from past relationships that changed how you approach love?
57. How do you feel about “relationship goals” on social media — realistic or overrated?

1. What’s something romantic you’ve always wanted to try but haven’t yet?
2. What song do you compare our relationship to?
3. Do you believe people can fall in love more than once?
4. What’s your favorite romantic movie and why?
5. If you could plan the most over-the-top date ever, what would it include?
6. What’s the sweetest thing someone’s ever done for you?
7. What’s your dream song to slow dance to—with the right person?
8. Do you think timing matters more than chemistry?
9. What’s your love story “green flag” moment?
10. If you could spend one magical night anywhere in the world with someone you love, where would you go?
11. What’s a small romantic gesture that always gets to you?
12. What’s your favorite way to show someone you care?
13. Do you think love should feel effortless or take work?
14. What’s a romantic cliché you secretly love?
15. If someone wrote a love letter to you, would you keep it forever?
16. What’s your definition of “the one”?
17. If love was a color, what would it look like to you?
18. What’s the best relationship advice you’ve ever received?
19. Have you ever had a moment that felt like it was straight out of a romance movie?
20. What’s one memory you hope to make in your next relationship?
21. Do you believe some people are meant to be?
22. How do you know when you’ve really caught feelings for someone?
23. What kind of love do you want to give — and receive?
24. What’s your favorite couple trope from books or movies?
25. If you could plan the perfect “just because” date, what would you do?
26. What kind of future do you dream about sharing with someone?
27. What romantic song always hits you in the feels?
28. Do you think soulmates have to be romantic, or can they be platonic?
29. Would you rather get a surprise romantic gesture or plan one yourself?
30. What do you think makes two people truly compatible?
31. How do you know when you’re ready to fall in love again?
32. What’s a place in your city that suddenly feels romantic because of us?
33. What scent (candle, cologne, our laundry) instantly makes you think of us?
34. What’s a “just because” surprise you’ve always wanted to plan for someone?
35. Which classic date do you think is underrated and deserves a comeback?
36. If we recreated a famous movie kiss, which one would you pick?
37. What’s a line from a song or poem that reminds you of us (no pressure to be perfect)?
38. What kind of weekend getaway feels the most like “us” — cozy cabin, beach bungalow, art-city wander?
39. Which photo of us feels the most romantic to you—and why that one?
40. What’s your ideal “rainy day” date at home with me?
41. What’s a compliment you love hearing from me that I should say more often?
42. What’s a love tradition from another culture you think is beautiful?
43. What’s your favorite way to show up for someone without words?
44. What’s a tiny habit that feels unexpectedly romantic to you?
45. If we were to make a couple’s playlist, what vibe would track one set — and what would you name it?

1. What’s a belief you had as a kid that you still secretly hold onto?
2. When do you feel the most like you're truly living?
3. What’s something you wish more people understood about you?
4. Is there a moment in your life you wish you could relive — not to change it, but just to feel it again?
5. What’s one thing you’ve never told anyone because you thought they wouldn’t get it?
6. What’s your personal definition of success, and has it changed over time?
7. If your younger self could see you now, what would they say?
8. What’s one moment that shaped who you are but no one really knows about?
9. Do you think people are mostly good, or do we all just pretend to be?
10. What’s something you’re still trying to forgive yourself for?
11. What’s one thing you want to be remembered for, not just remembered as?
12. When’s the last time you felt completely at peace?
13. Do you think you’re more driven by love or fear?
14. What emotion do you struggle to express the most?
15. What’s a dream you’ve quietly let go of?
16. If someone wrote a biography about your life, what would the title be?
17. What’s one part of growing up that no one prepared you for?
18. What do you think people misunderstand about vulnerability?
19. If you had to teach a life lesson to someone younger than you, what would it be?
20. Do you believe people can really change — or just adapt?
21. What’s something that used to scare you but doesn’t anymore?
22. How do you define emotional intimacy?
23. What does “home” mean to you — and is it a place, person, or feeling?
24. What’s the hardest truth you’ve had to accept about yourself?
25. What do you think your purpose is right now — not forever, just in this season?
26. What’s a hard choice you made that ended up being the right one?
27. If you could ask your future self one question, what would it be?
28. What’s a boundary you think everyone should have in relationships?
29. What’s your favorite way to celebrate our relationship milestones, big or small?
30. What’s one little thing I do that always makes you feel loved?
31. How has our relationship changed the way you see yourself?
32. What do you think we’re best at as a couple?
33. What’s a challenge we’ve faced together that you’re proud we got through?
34. Do you think we communicate better now than when we first started dating?
35. What’s one memory of us you never want to forget?
36. How do you think we’ve grown since the beginning of our relationship?
37. What’s something you’ve learned about love from being with me?
38. Do you think we balance each other’s strengths and weaknesses? How?
39. What’s a small ritual we could add to our weeks that would feel romantic without trying too hard?
40. What’s your favorite inside joke we share?
41. How has our relationship surprised you?
42. What do you think makes us compatible on a deeper level?
43. When did you first realize this relationship could be serious?
44. What’s one way you think we bring out the best in each other?
45. Do you feel like we’ve created our own “language” or rhythm as a couple?
46. What’s a value or belief we share that feels important to our relationship?
47. What’s your favorite thing about the way we support each other?
48. Is there a moment with me that made you feel especially seen or understood?
49. What’s a future anniversary tradition you’d love us to start?
50. What’s your favorite way to slow down together when life gets hectic?
51. What part of our relationship feels the safest to you?
52. How do you think we handle disagreements compared to other couples you know?
53. What’s a tradition or ritual we’ve started that you hope we always keep?
54. Do you think being with me has changed how you show love?
55. What’s one thing you admire about the way I approach our relationship?
56. When do you feel the closest to me?
57. What do you think is the biggest difference between the “us” at the start and the “us” now?
58. What’s a lesson you think we’ve taught each other as partners?
59. How do you picture us five years from now, in terms of our connection—not just logistics?
60. Is there a time you felt really grateful for our relationship but didn’t say it out loud?
    What’s something you think only we understand about each other?
61. What do you think our relationship has taught you about love in general?