250 questions to ask your boyfriend (fun, cute & romantic)

This massive list of questions to ask your boyfriend make great conversation starters and will help you get to know him much better.

The list is divided into sections, including fun questions to make him laugh, romantic questions to help you learn how he feels about you, and serious questions to help you connect on a deeper level.

Fun questions to ask your boyfriend

Studies have shown that people will like you more if you make them laugh. These fun questions will get your boyfriend laughing, but you can still learn a lot about what he thinks about love and life!

1. Who would you pick if you could be stranded on a desert island with one person? (and it can’t be me).
2. Should you put pineapple on pizza?
3. What name could you never give our child because you hate someone with that name?
4. If you could trade lives with anyone for one day, who would you pick and why?
5. What two things should never go together?
6. What’s the worst movie you’ve ever seen?
7. What’s an embarrassing habit you can’t get rid of?
8. Would you rather swim with sharks or jellyfish?
9. What’s something about yourself that you’ve never told anyone else?
10. What’s the weirdest thing you’ve ever Googled?
11. Who should play you in a movie about your life and why?
12. What’s the first thing you do when you have the house to yourself?
13. If you had a warning label, what would it say?
14. Would you rather have $50 cash today or $100 cash one year from today?
15. What is one unique talent you have that most people wouldn’t expect from you?
16. What’s your favorite type of music? What are your top 5 favorite songs right now?
17. If you could have one superpower, what would you choose?
18. What’s the worst thing you’ve ever spent money on?
19. What’s the most spontaneous thing you’ve ever done?
20. What’s the biggest band you’ve ever seen live?
21. If you could only keep three possessions, what would they be?
22. What is the stupidest thing you believed when you were a kid?
23. What trashy TV show is your guilty pleasure?
24. What’s the latest you’ve ever stayed in your pajamas?
25. What’s the longest you’ve ever stayed awake?
26. What’s one thing your friends think is fun that you don’t?
27. What’s your favorite way to end a long day?
28. What would you do if you could be girl for one day?
29. If you could pick anywhere to live in the world, where would it be?
30. What would you do if all your Facebook friends turned into zombies?
31. What do you think I’m most likely to go viral for?
32. Would you rather live in the mountains or on the beach?
33. What’s the funniest thing you’ve ever done drunk?
34. If there was no risk of getting caught or hurt, would you ever commit a crime?
35. What is your favorite birthday experience ever?
36. What’s the best thing that’s happened to you this year?
37. If you could only eat one meal for the rest of your life, what would it be and why?
38. Have you ever gotten a detention in school?
39. If a genie granted you three wishes, what would you wish for?
40. What was your childhood nickname, and how did you get it?
41. What would you choose as your last meal?
42. If you could only wear one thing for the rest of your life, what would you choose?
43. What do you think about when you can’t sleep at night?
44. What’s the most crazy facial expression you can pull?
45. What’s your favorite animal and why?
46. Do you have a phone voice voice?
47. What is something that gets on your nerves that no-one else seems to care about?
48. If you could only ever watch 5 movies again, what would they be?
49. What trend do you hope will never go out of style?
50. Are you afraid of roller coasters?
51. What’s your favorite flavor of ice cream?
52. If we started a band together, what would our name be?
53. How do you relax?
54. What’s a funny story you’ve always wanted to tell someone?
55. If someone has food in their teeth, do you tell them or ignore it?
56. What’s your favorite musical artist of all time?
57. What world record do you think I could set?
58. What crazy hobby would you take up if you become a billionaire?
59. What’s your favorite movie of all time?
60. What would be the first thing you do if you won the lottery?
61. What word have you always pronounced wrong but never realized?
62. What’s the most embarrassing thing that’s ever happened to you?
63. Would you rather be rich and famous or rich and anonymous?
64. What’s the funniest voice you can do?
65. If you could go anywhere in the world right now, where would you go?

Cute questions to ask your boyfriend

Sometimes you want to make him laugh, but sometimes you want to show him your cute and flirty side. These cute questions will help your relationship grow as he opens up about the way he feels about you.

1. Who was your first crush?
2. What would you do if I told you I wasn’t wearing any underwear?
3. Do you ever get jealous if you see me talking to another guy?
4. What’s your favorite position to cuddle in?
5. At what point did you feel like we were getting serious as a couple?
6. If you could change one thing about how I look, what would it be and why?
7. What one word do you hope people use when then describe you?
8. What was your first impression of me?
9. What’s your favorite place to be massaged?
10. If we have kids, what features would you like them to get from each of us?
11. Would you rather we went camping or stayed in a luxury hotel?
12. What’s the best compliment anyone has ever given you?
13. When does my face look its absolute worst?
14. What do you think is your best physical feature?
15. How would you describe me in three words to a stranger?
16. What was the last dream you remember having?
17. If you had to describe me in three words, what would they be?
18. What celebrity do I remind you of the most?
19. How do you describe me to your friends?
20. Can you give me a random compliment right now?
21. Do you think it’s important for a guy to be able to cook?
22. How would your best friends describe you in one sentence?
23. Have you ever cried while watching a sad movie?
24. Do you like it when I wear my hair up or down?
25. Do public displays of affection make you embarrassed?
26. What are the biggest things that attracted you to me when we first met?
27. Do you think I care about my appearance too much?
28. Are you a morning person or a night owl?
29. Would you prefer me to be good in the bedroom or good in the kitchen?
30. What song reminds you of me?
31. Was there anything you were scared I would learn about you when we started dating?
32. What was the first thing you noticed about me that attracted you?
33. If I was interviewing for a job as your friend, what questions would you ask me?
34. Who is the sexiest anime or cartoon character of all time?
35. How would you handle it if I broke up with you?
36. If you wrote romance novels, what would your pen name be?
37. Do you like sleeping on your back or stomach?
38. What would you do if you saw me having fun with another guy?
39. What do you like the most about our relationship?
40. If we had only $10 left after paying our bills for one month, what would we spend it on and why?
41. What quality in a girl turns you off the most?
42. Which one of my friends do you find most annoying?
43. Would you laugh with me or at me when I do something embarrassing?
44. Where is your favorite place for us to go on a date?
45. What celebrity would you want a free pass to have sex with?
46. How old were you when you had your first kiss?
47. What are your favorite drinking games?
48. What outfit do you think I look sexiest in?
49. Do you think I’m more cute or sexy?
50. What’s something strange or embarrassing you’ve always wanted to ask me?
51. What is something about me that you wish I would stop doing?
52. What’s your favorite thing to do in the morning when you first wake up?
53. What’s the sexiest dream you’ve ever had about me?
54. What’s the weirdest thing about me that you love?
55. Do you prefer a girl to make the first move?
56. Have you ever had a crush on someone who didn’t know about it?
57. If you could dress me up in anything, what would it be?
58. What’s the craziest thing you’d do to make me happy?
59. What is one thing about me that makes you happy?
60. What do you think is my best physical feature?

Romantic questions to ask your boyfriend

If your relationship is at the point where you feel comfortable talking about love and relationships, use these questions as a starting point to find out what he thinks about things like sex, marriage, and even your future together!

1. If you could pick anywhere to go on a romantic vacation with me, where would it be?
2. What can I do to make your day better?
3. What is your favorite thing that I do for you, not in bed?
4. How would you describe our relationship to someone if they asked about it?
5. What does it mean to you to be in love?
6. If we weren’t in public, what would you like to do to me right now?
7. Do you believe in love at first sight?
8. What makes a person truly beautiful inside out?
9. Do you have any unfulfilled sexual fantasies?
10. Do you prefer having sex in the morning or the evening?
11. If I had to move to another country, would you come with me?
12. Am I someone you feel like you can depend on for emotional support?
13. Do you ever think about our future together?
14. Do you think I’m funny, serious, or a bit of both?
15. What do you think should be your reward for being a good boy today?
16. What is your favorite thing about me as a person and as a girlfriend?
17. What is your idea of a perfect date?
18. What’s the best date we’ve ever been on together?
19. What are the best and worst parts of our relationship so far?
20. How many times have you been in love?
21. How would you describe my sense of humor?
22. What was the first thing you thought about this morning?
23. If you could take away any one of my bad habits, which would you choose and why?
24. Could you be in a long distance relationship?
25. If we broke up, what’s the thing you’d miss about me the most?
26. Who was your first kiss with, and how old were you when it happened?
27. If you could relive any moment in our relationship, which would you choose?
28. What is the most romantic thing anyone has ever done for you?
29. What’s your favorite part of my body to kiss?
30. How is our relationship different to what you thought it would be?
31. What’s something you’d love to do with me that you’ve never done before?
32. How have you been feeling lately?
33. What thing do you like the most that I do in bed?
34. Where do you want to go on our honeymoon if we get married?
35. When did you first realize that you loved me?
36. Do you believe in love at first sight?
37. Is there anything you want to say to me but you’ve felt you couldn’t?
38. Would it bother you if I forgot something important like your birthday?
39. Would you ever have sex in public?
40. What part of your body do you like me to kiss the most?
41. Who was your first girlfriend, and how am I different from her?
42. Is there something in your life that’s making you stressed or nervous? How can I help?
43. Do you think that finding true love is fate or chance?
44. What is your favorite sexual fantasy?
45. Have any relationships from your past affected your relationship with me?
46. If you had to choose a new pet name for me, what would it be?
47. What’s the best thing about our relationship?
48. Do you think we will still be together in 2 years?
49. Do you like the fact that we’re getting more serious?
50. What laws would you break to save me?
51. Do you remember the first time we met?
52. What’s the most romantic thing you’ve ever done for someone?
53. How would you describe yourself as a boyfriend?
54. What’s your favorite way to show me that you love me?
55. Am I a better kisser or are you?
56. If you think about us having sex, what position are we in?

Serious questions to ask your boyfriend

When you really care about someone, you want to learn more about who they are and how they think. These juicy questions for your boyfriend will help the two of you communicate better and get to know each other on a deeper level.

1. Do you believe humans are fundamentally good or bad?
2. What aspects of your childhood would like to pass on to your children?
3. What’s your biggest fear in life?
4. What have you achieved in your life that makes you the most proud?
5. What time in your life have you felt the most alone?
6. What is your dream job?
7. How would you describe yourself to someone who doesn’t know anything about you?
8. Who is your best friend and why?
9. If you could give your younger self one piece of advice, what would it be?
10. Have you ever been in a situation that challenged your faith in humanity?
11. What would you want to change about us as a couple?
12. When was the last time I disappointed you, and how did it make you feel?
13. Do you think bad things happen for a reason or no reason at all?
14. What is the weirdest dream you’ve ever had?
15. What were some of your favorite childhood memories?
16. Is it better to live a pleasant yet unfulfilling life or an unpleasant yet fulfilling one?
17. What’s your biggest insecurity?
18. Is time travel possible or just a fantasy?
19. What’s the one thing you wish you could change about yourself?
20. What do you imagine when you think of home?
21. Can we ever truly understand what goes on inside other people’s heads?
22. Who is an example of true loyalty to you, and why?
23. What’s the most important thing in a friendship?
24. Do you think that people should always forgive?
25. What’s the most important thing a person needs to be truly fulfilled in life?
26. What’s the hardest thing you’ve ever had to do?
27. What is your definition of success?
28. Why do bad things happen to good people?
29. If you could change anything about your past, what would it be?
30. What is your happiest memory?
31. Who do you think has the most influence on who you’ve become?
32. Why do people lie when there’s no benefit in doing so?
33. Would you rather have all the answers right now or keep on searching for new questions forever?
34. Can money buy happiness?
35. Is it possible to remain best friends with an ex after breaking up with them?
36. Are you closer to your mom or dad?
37. Do I make enough effort for our relationship, or do you wish I made more?
38. What do you think are the biggest differences between us?
39. What do think is most important aspect of life?
40. What area of our relationship do you think needs the most work?
41. What have you struggled with in life that nobody knows about?
42. What’s your biggest regret in life?
43. What’s the most important thing I can do for you to make you happy?
44. What are three things you want to achieve this year?
45. How do you think we can know each other on a deeper level?
46. When have you felt the lowest in your life, and how did it affect you?
47. Has anything made you cry in the last year?
48. If you could relive one day of your life over and over, which would it be?
49. How satisfied are you with where life has taken you so far?
50. When you picture your ideal future, what do you see?
51. What kind of legacy would you like to leave for your family and future generations?
52. What are the things in your life you could never compromise on?
53. Which feeling is worse – worry or guilt?
54. What is your relationship like with your family?
55. How do you think you’ve changed as you’ve gotten older?
56. How would you react if someone insulted me in front of you?
57. Do you find it difficult or easy to trust people?
58. Have you ever gotten petty revenge on somebody? What did you do?
59. Will robots take over all our jobs in the future?
60. How have you been feeling lately?
61. Is there something in your life that’s making you stressed or nervous? How can I help?
62. Is there anything we could do together to strengthen our relationship?
63. What do you think is the strongest part of our relationship?
64. What experiences have most shaped how you see the future?
65. What is your ultimate goal in life?
66. What’s the biggest problem the world is facing?
67. What memory has had the biggest impact on your life?
68. Would you sacrifice your life for someone?
69. What’s the most traumatic thing that’s ever happened to you?

How to ask your boyfriend personal questions

Here are some great tips when chatting to your boyfriend and getting to know him better.

Listen carefully to how he responds. If he’s being evasive or tries to get off the subject, gently bring him back to it by pointing out that you are interested in his thoughts.

Be gentle but persistent. It can take some time for a guy to open up, so don’t give up if he doesn’t answer your questions straight away! There’s no ‘right’ or ‘wrong’ answer. The point is that you’re trying to get to know him better, and he’s giving you a glimpse into his personality.

Pay close attention to his nonverbal cues as you talk. You can learn a lot by observing his body language and facial expressions. Don’t be afraid to follow up on your questions later, especially if he seems reluctant to answer the first time.

Use these questions as conversation starters, but don’t be afraid to go off-topic and talk about other things as well. These questions are just to help you get started!