301 Deep, Funny, and Flirty Questions to Ask Your Boyfriend

You know those nights when you’re curled up on the couch, phones finally put away, and you realize… you want to talk, but don’t know what to talk about?

That’s where this list comes in.

After being with Matthew for years (and still finding out the weirdest little facts about him—like his fear of geese?!), I’ve learned that asking the right questions can totally shift the mood.

It can turn a regular night into a heart-to-heart, a giggle-fest, or even a spontaneous makeout session (just sayin’…).

This list isn’t just about relationship check-ins. It’s about connection. Curiosity. And sometimes, just pure fun.

Inside, you’ll find 301 questions to ask your partner, organized by mood:
– The deep ones, for those late-night soul-searching convos
– The funny ones, when you just want to laugh your faces off
– The flirty ones, to turn up the heat (or the butterflies)
– Plus thoughtful, random, romantic, and future-focused questions for every kind of moment.

Honestly, some of the best conversations I’ve had with Matthew happened in the most ordinary moments—laying in bed with the lights off, stuck in traffic, or waiting for takeout to show up.

So go ahead—ask one question tonight. Just ONE 😊

It might lead to a deep talk, a burst of laughter, or a “wow, I didn’t know that about you” kind of moment. And that’s the good stuff.

Why Asking Questions Matters in a Relationship

You might think you already know everything about your boyfriend—his favorite pizza topping, the show he re-watches for comfort, the exact face he makes when he’s pretending not to cry during a Pixar movie (Matthew, I’m looking at you).

But here’s the truth: There’s always more to learn. Always more to feel together.

Asking questions—real questions, silly ones, even the awkward kind—can do something kind of magical:
It creates space. Space to open up, laugh, reflect, and just be yourselves with each other.

Here’s why I believe these little conversations matter more than we realize:

• They build emotional intimacy. You get to understand each other’s inner world, not just the surface stuff.
• They strengthen trust. When you ask, and really listen, your partner feels seen—and that’s powerful.
• They keep things fresh. No one wants to talk about grocery lists 24/7. This brings back the fun and surprise.
• They deepen love over time. Even after years together, hearing your partner say, “No one’s ever asked me that before,” hits differently.

And it’s not about finding the “perfect” question—it’s about being curious with each other.

Even five minutes of playful, honest conversation can shift the whole energy between you.

So don’t wait for a relationship milestone or a deep talk cue—ask now. Ask often. Ask with love.

Get-to-Know-You Better Questions

Even if you think you know everything about your boyfriend, these questions might surprise you (and him).

Use them to explore his past, his personality, and all the little things that make him who he is.

1. What’s your earliest childhood memory?
2. What’s something you believed as a kid that turned out to be totally wrong?
3. If you could relive one day of your life, which would it be?
4. What’s a smell that instantly brings back a memory?
5. Who was your childhood hero?
6. What’s the weirdest nickname you’ve ever had?
7. What’s one thing you wish people understood about you?
8. What’s your favorite meal your mom or dad used to make?
9. What kind of student were you in school?
10. What’s a random skill or fact you’re secretly proud of?
11. What’s something you’ve never told anyone before?
12. If you had to describe your personality in 3 words, what would they be?
13. What’s the most “you” thing you’ve ever done?
14. When do you feel most confident?
15. Who really shaped the person you are today?
16. What’s your favorite way to spend a lazy Sunday?
17. What were you like in high school—and how do you think you’ve changed since then?
18. What’s something small that always makes you feel better?
19. Is there a book, movie, or song that changed your life a little?
20. What’s something you’re still figuring out about yourself?
21. What’s your biggest non-serious pet peeve?
22. What’s your go-to comfort show or movie?
23. Do you believe in luck or fate?
24. What’s something you always wanted to try but haven’t yet?
25. What’s your favorite thing to do when no one’s watching?
26. What makes you feel truly at peace?
27. What’s one tradition you want to carry into your future family?
28. What did you want to be when you were little?
29. What’s your most random hobby or interest?
30. What makes you feel instantly nostalgic?
31. What kind of grandparent do you think you’d be?
32. What’s something you’ve outgrown—but still miss?
33. If you had to eat one meal every day for a year, what would it be?
34. What’s a fear you’ve gotten over as you’ve grown up?
35. What’s your ideal way to spend a weekend?
36. What was your favorite toy or game as a kid?
37. If you could time travel, would you go to the past or the future?
38. What’s the weirdest coincidence you’ve ever experienced?
39. If your life had a theme song, what would it be?
40. What’s something that always makes you feel like a kid again?
41. Have you ever had a mentor? What did they teach you?
42. What’s something you’ve learned the hard way?
43. Who in your life do you admire most—and why?
44. What’s your “fun fact” about yourself that always surprises people?
45. What’s your dream job if money didn’t matter?
46. What’s something you secretly love that might surprise me?
47. What’s your favorite type of weather—and how does it affect your mood?
48. What’s a moment from your past you replay sometimes?
49. What does your ideal day look like from start to finish?
50. What’s something you think everyone should try at least once?
51. When was the last time you felt truly proud of yourself?
52. What’s a sound that makes you feel calm?
53. What do you think people misunderstand about you most often?
54. If you could redo one decision from your past, would you?
55. What’s something you wish you were better at—but enjoy anyway?
56. Who do you think knows you best in the world?
57. What’s one thing you always carry with you—literally or emotionally?
58. If you had to teach a class on one thing, what would it be?
59. What does “home” mean to you?
60. What’s one question you wish people asked you more often?

Funny and Silly Questions

Save these for road trips, lazy Sunday mornings, or nights when you’re both a little slap-happy.

Some are totally RIDICULOUS—and that’s the point 😊

1. If you had to be a cartoon character for a day, who would you pick?
2. What’s your weirdest talent that’s completely useless?
3. If animals could talk, which one would be the sassiest?
4. What’s the most embarrassing thing you’ve ever done in public?
5. Would you rather fight one horse-sized duck or a hundred duck-sized horses?
6. What’s your go-to karaoke song—and how dramatic do you get?
7. What’s a food combination you swear by (but everyone else hates)?
8. What’s your most irrational fear?
9. If you had to wear one Halloween costume every day for a year, what would it be?
10. What’s the most ridiculous argument you’ve ever had?
11. What’s the worst haircut you’ve ever had?
12. Which celebrity would play you in a bad comedy about your life?
13. If your farts made a sound (besides, you know, that), what would it be?
14. What’s something super random that makes you laugh every time?
15. Have you ever had a cringey AIM or Instagram username?
16. If your life were a reality show, what would it be called?
17. What would your drag name be?
18. What’s a trend you totally fell for (and now regret)?
19. If you could swap lives with a fictional character, who would it be?
20. What’s your go-to “pretend you know what you’re doing” face?
21. What’s the weirdest thing you believed as a kid?
22. What would your personal theme park be called—and what rides would it have?
23. Have you ever laughed so hard you cried (or snorted)?
24. What’s your most iconic childhood outfit?
25. If you had a warning label, what would it say?
26. What’s your guilty pleasure TV show?
27. Would you rather always smell like garlic or never be able to use deodorant again?
28. Have you ever accidentally insulted someone?
29. If aliens came to Earth and asked you to represent humanity, what’s the first thing you’d do?
30. If you had to rename yourself using only kitchen items, what would it be?
31. What animal do you think matches your personality the most?
32. What’s the most awkward thing you’ve said on a first date?
33. If you were a potato dish, how would you be cooked?
34. What’s your signature dance move?
35. What word do you always mispronounce in your head?
36. What’s the most embarrassing autocorrect fail you’ve sent?
37. What’s something that shouldn’t be funny but always makes you laugh?
38. If you opened a restaurant, what would be on the kids’ menu?
39. What’s your zombie apocalypse plan?
40. If you could be a fly on the wall for any conversation, what would it be?
41. What’s your favorite “bad” movie?
42. If you had to live in a movie for a month, which one would you choose?
43. What’s something you secretly find hilarious but know you probably shouldn’t?
44. What’s a TikTok trend you actually enjoy?
45. Would you rather sneeze glitter or burp confetti for the rest of your life?
46. If your laugh had a color, what would it be?
47. What’s your go-to fake name at coffee shops?
48. Have you ever had a “foot-in-mouth” moment that still haunts you?
49. What would your cringey high school yearbook quote be today?
50. If you were a cereal, what would your slogan be?
51. What’s your most random Google search lately?
52. Would you rather always have an itch you can’t reach or a sneeze that never comes?
53. If you could prank any celebrity, who would it be and what would you do?
54. Have you ever said something out loud that you meant to keep in your head?
55. If your life were turned into a meme, what would the caption be?
56. What’s your signature awkward silence move?
57. If your life had a laugh track, what moment would play it the most?
58. What’s your “embarrassing but endearing” habit?
59. If you had to wear socks with your face on them, how would you style them?
60. What’s your weirdest recurring dream?

Deep and Meaningful Questions

These are perfect for long conversations, slow weekends, or nights when you’re both feeling a little more open than usual.

Ask gently. Listen fully. You never know what beautiful truth might come out.

1. What’s one moment that changed the way you see the world?
2. When do you feel most like yourself?
3. What does “being loved” mean to you?
4. What are you most afraid of losing?
5. What’s something you’ve forgiven someone for—but still think about?
6. How do you handle emotional pain?
7. What’s a truth you’ve had to learn the hard way?
8. What legacy do you want to leave behind?
9. When do you feel most vulnerable?
10. What’s something you’re still healing from?
11. What’s your relationship like with your inner voice?
12. What makes you feel grounded when life gets overwhelming?
13. How do you define success?
14. What’s one belief you’ve outgrown?
15. What kind of impact do you want to have on people?
16. What’s the hardest decision you’ve ever made?
17. Who do you admire most—and why?
18. What emotion do you struggle to express?
19. What does “home” mean to you?
20. When was the last time you truly felt at peace?
21. What’s something you’ve never told anyone but feel safe telling me?
22. What are you afraid people might misunderstand about you?
23. When do you feel the most loved by me?
24. What’s a memory that still brings up strong emotion—good or bad?
25. Do you believe everything happens for a reason?
26. What’s your love language—and do you feel like it’s spoken enough?
27. How do you feel about change?
28. When did you feel most proud of yourself?
29. What’s something you’re scared to want?
30. Do you believe people can truly change?
31. What does forgiveness look like to you?
32. What’s your relationship like with your past self?
33. Have you ever had your heart broken?
34. What’s one thing that always makes you feel safe?
35. What’s something you wish more men talked about openly?
36. What does emotional intimacy mean to you?
37. How do you react when someone hurts you?
38. What’s something you’re deeply passionate about but rarely share?
39. What’s a truth about yourself you’ve only recently accepted?
40. How do you want to grow in this relationship?
41. What’s a fear that’s held you back?
42. What kind of partner do you hope to be in 10 years?
43. What part of your childhood shaped you the most?
44. What are you still learning about love?
45. What’s something you want to be better at emotionally?
46. What brings you quiet joy?
47. What memory would you keep if you could only keep one?
48. Do you believe in soulmates?
49. What’s one thing that always moves you to tears?
50. How do you want to be remembered?
51. What’s something you’re grateful for—but don’t say often enough?
52. What’s one thing about our relationship that makes you feel secure?
53. What helps you open up when you’re feeling shut down?
54. What’s your definition of emotional safety?
55. What’s something you hope I always understand about you?
56. What’s one piece of advice you’d give your younger self?
57. What’s something you never thought you’d share with someone—but you’ve shared with me?
58. What does vulnerability look like for you?
59. What scares you the most about the future?
60. What does unconditional love mean to you?

Flirty and Romantic Questions

Use these on a cozy date night, over texts during the day, or when you’re both feeling that butterflies-meets-best-friends kind of energy.

1. When did you first realize you had a crush on me?
2. What do you remember about our very first kiss?
3. What’s your favorite thing I do that drives you a little wild?
4. What do you think is the most attractive thing about me?
5. Do you like it when I flirt with you in public—or in secret?
6. What was your first impression of me—really?
7. How do you know when you’re falling in love?
8. What’s your favorite thing about the way I look when I’m not trying?
9. What moment with me makes your heart race every time you think about it?
10. What outfit of mine do you love the most?
11. Do you remember the first time we held hands?
12. What’s your favorite place I’ve ever kissed you?
13. If we were in a rom-com, what would our love story be called?
14. What’s one thing I do that makes you feel special?
15. What’s a moment with me you wish you could relive?
16. What’s something small I do that turns you on?
17. What does being in love feel like to you?
18. What song reminds you of me?
19. What’s something romantic you’ve always wanted to try?
20. How do you feel when I look at you like that?
21. What part of me do you love kissing the most?
22. How would you describe my “flirty face”?
23. What’s one way I make you feel sexy without even realizing it?
24. Would you rather kiss me in the rain or under the stars?
25. What’s something you’ve never said out loud—but think about when we’re together?
26. What’s one thing I do that always makes you smile—even when you’re annoyed?
27. If you had to write a love letter to me, what’s the first sentence?
28. What’s your love language—and do you think I speak it well?
29. What kind of romantic surprise would really wow you?
30. Do you think we’d still fall in love if we met in a different life?
31. What’s your favorite kind of cuddle: forehead-to-chest or legs tangled?
32. What’s a memory of us that feels like a movie scene?
33. What’s something about me you’re completely obsessed with—but haven’t told me yet?
34. What’s the most romantic thing you’ve ever done—or want to do—for me?
35. If we could spend a full day in bed together, what would we do (besides nap)?
36. What kind of date night always puts you in a flirty mood?
37. Do you ever replay our first few conversations in your head?
38. What does “chemistry” mean to you—and do we have it?
39. What’s the flirtiest thing I’ve ever said to you?
40. What’s your favorite kind of kiss—slow and sweet or fast and playful?
41. Do you think we flirt more with words or with looks?
42. What’s your favorite pet name I call you—and which one secretly makes you blush?
43. If we ran away together right now, where would we go?
44. What’s one thing I do that makes your heart skip a beat?
45. If we were characters in a steamy novel, what would our storyline be?
46. What’s something about our relationship that feels totally unique to us?
47. Do you remember what I was wearing the first time you really noticed me?
48. How would you describe my “I’m thinking about you” face?
49. What’s a totally random moment when you felt really attracted to me?
50. If I sent you a flirty selfie right now, what would you want it to look like?
51. What do you think our future kisses will feel like 10 years from now?
52. When do you feel most connected to me physically and emotionally?
53. What’s one compliment I’ve given you that you’ll never forget?
54. What’s your favorite kind of physical touch from me?
55. If you had to plan a surprise romantic night, what would it include?
56. What’s something you want to try together that we haven’t yet?
57. What’s your secret for making me melt (and do you know it works)?
58. What would we do on a dream weekend getaway together—no budget, no schedule?
59. Do you feel like I really see you—and what does that mean to you?
60. What’s one flirty promise you’d make me right now?

Serious and Future-Focused Questions

These questions are thoughtful, honest, and sometimes a little vulnerable.

They’re the kind you ask when you’re talking long-term, making plans, or just wondering what life might look like down the road—with him by your side.

1. What kind of life do you imagine for yourself in five years?
2. Do you want to get married someday?
3. How do you feel about becoming a parent?
4. What does financial stability look like to you?
5. How do you handle long-term stress or pressure?
6. What do you want our future home to feel like?
7. How do you define commitment in a relationship?
8. What are your biggest priorities in life right now?
9. What does “success” look like for you?
10. How important is work-life balance to you?
11. What kind of legacy do you want to leave behind?
12. How do you deal with conflict in a relationship?
13. Do you believe couples should share everything—or keep some independence?
14. What’s your ideal way to handle disagreements as a couple?
15. Do you see us growing together—even when life gets hard?
16. What’s your dream city or country to live in someday?
17. Are you more of a “settle down early” or “take our time” kind of person?
18. What are your non-negotiables in a serious relationship?
19. Do you believe love can last forever?
20. What kind of partner do you want to be—now and in the future?
21. How do you want to raise kids (if you want them at all)?
22. Would you rather rent forever in a cool city or buy a home in the suburbs?
23. How do you picture retirement?
24. What values do you want to pass on to your future family?
25. How do you want to handle money as a couple—shared, separate, or hybrid?
26. What would you do if one of us had to relocate for work?
27. What scares you about the future?
28. What excites you most about our future together?
29. How do you want to celebrate big life milestones?
30. What’s something you’re still working on emotionally?
31. Would you be willing to go to couples therapy if we ever needed it?
32. How do you think relationships change over time?
33. Do you believe in traditional gender roles in a relationship?
34. What’s your biggest long-term goal—and how can I support it?
35. How do you think we’ll grow as individuals and as a couple?
36. What does loyalty mean to you?
37. How do you handle temptation or insecurity in a relationship?
38. What scares you about commitment, if anything?
39. What’s a challenge you think we might face—and how would we get through it?
40. What do you hope never changes about us?
41. How do you feel about growing old with someone?
42. What would make you feel 100% ready to take the next step with me?
43. What does “home” look like to you in the future?
44. What’s a dream we can start planning together now?
45. How do you want to spend your 30s, 40s, 50s?
46. What’s your plan for balancing ambition with time for love and family?
47. What kind of relationship did your parents have—and how has that shaped your view?
48. What’s something you hope we never stop doing, no matter how old we get?
49. How do you feel about religion, spirituality, or faith in a future partnership?
50. What kind of wedding would you want someday?
51. What would be your ideal timeline for marriage or kids (if you want them)?
52. If we had a major disagreement, how would you want us to work through it?
53. What’s a fear you have about being in a serious relationship?
54. What makes you feel safe enough to be all-in?
55. Would you rather grow slow and steady—or fall fast and deep?
56. How would you handle it if our dreams started pulling us in different directions?
57. What’s one thing that would make you know I’m “the one”?
58. What does “forever” mean to you in love?
59. What’s a promise you’d make to me about our future?
60. What do you imagine our life will look like 20 years from now?
61. What’s one future we could build together that excites you most?

The Right Questions Bring You Closer

Here’s the thing: love isn’t just made in the big, sweeping gestures.

It’s built in the tiny, curious moments—the unexpected answers, the laughter in between, the way you both pause and say, “Wait, I didn’t know that about you!”

These 301 questions aren’t about checking boxes or finding out everything at once.

They’re about showing up. Getting curious. Saying, “I want to know more of you,” again and again, even after you think you’ve heard it all.

And if you’re here because things feel a little QUIET between you two lately—like you’re sitting next to each other but not really connecting—I just want you to know something: you’re not the only one.

Sometimes love doesn’t fade, it just gets a little buried under life.

And a simple question—asked with real curiosity—can be the start of finding your way back to each other.

So use this list however you want—on road trips, cozy nights in, or even via text when you miss each other.

Let it spark connection, conversation, and maybe even a few butterflies.

Because the truth is: the BEST relationships aren’t built on having all the answers…

They’re built on never being afraid to ask the next question.