If you’re out on a date and wishing you had some fun questions to ask your boyfriend, you’re in luck! This fun list is packed full of interesting, and creative questions to ask a guy you like, along with some deeper questions to ask a guy you have been seeing for a while!

You probably know how to start a conversation with a guy, but sometimes it can feel like the dialogue kind of stalls out.

These questions will help things going again, and are sure to lead to some fun discussions!


7 Best Questions To Ask Your Boyfriend

These are the best of the best questions, great for starting a conversation any time. You don’t have to do them in order, just find a few that sound fun!

Don’t forget to take notes (maybe, later, so it doesn’t feel like a test!) - some of these have great info in them!

1. Do you consider yourself a happy person?

What is his definition of happy?

2. What is your favorite thing to wear to bed?

And if it's socks, it may be time to end things… kidding!

3. What would you say to your President if you ran into him randomly?

Would he be starstruck, or would he start hitting on some issues?


4. What do you feel is the world’s biggest problem right now?

And how would he fix it?

5. If money was not a factor, would you leave your job and travel the world?

If so, would he travel randomly, or make a detailed plan?

6. How do you waste your time?

Maybe it’s video games on his phone, scrolling Insta, or reading a good book.

7. You're in prison with a life sentence, what was your crime?

Get creative - there are lots of weird crime laws on the books!

7 Things To Ask Your Partner To Get To Know Him Better

If you want some questions to ask a guy to get to know him, this is the list for you! Find out what he likes, dislikes, what makes him tick!

8. Do you think money can buy happiness?

What can he buy that makes him happy?

9. How long was your longest relationship? Why did it end?

What would you do if you randomly ran into them?

10. What fictional character do you have a crush on?

It can be from a book, movie, comic, tv show - player's choice!

11. Where is your ideal place to live?

Is he a city mouse or a country mouse?

12. Would you ever go on a silent retreat?

When thinking of things to ask your boyfriend, it's a great idea to ask how he feels about taking contemplative time.

13. What is your deepest darkest secret that nobody else knows?

Remember to cross your heart, promise not to tell!

14. What is something you’re secretly insecure about?

Reassure him that you’ll never tease him about this.

7 Fun Questions to Keep the Conversation Going

So, you’re on a date and trying to get to know each other better, but the conversation gets a bit stuck. No fear, help is here!

These are some amazing, fun questions to ask a guy that will get you guys connecting in a whole new way!

15. How would you describe our first kiss?

Was it as good as he hoped, or more awkward than he expected?

16. Do you like when I touch your face?

Are there parts of it he doesn’t like touched? This might just be one of the best things to ask your boyfriend.

17. What's something I do, that I don't realize I do, that you love?

Maybe something silly, like twisting your hair.

18. Am I the kind of girl you’d take home to your parents?

Ask how his parents reacted to other girlfriends.

19. Has a sad movie ever made you cry?

Does he like to watch sad movies or does he feel manipulated?

20. If I was a dessert, what would I be and why?

Something thrilling like ice cream or decadent like lava cake?

21. What actor or actress would play you in a movie about your life?

Someone funny? Serious? Devastatingly handsome?

7 Weird Yet Funny Questions That Will Surely Make Him Laugh

Looking to add a little silliness in your relationship? That’s great! Studies show that couples that have fun together stay together longer!

Try using these funny questions to ask a guy to get some good, wholesome wit going on!

22. What is the most embarrassing thing someone has caught you doing?

And how did he recover??

23. What’s the food you like to have the most on your birthday?

Besides the birthday cake, of course!

24. Can you remember the funniest thing you ever did or said?

Have him describe why it was so hysterical.

25. What was your favorite thing to wear as a child?

Would he wear it now as an adult?

26. Did you have a nickname that you hated when you were a child?

Was it from a loving friend or a bully?

27. Out of all the world's languages, which one sounds funniest to you?

Which language does he think is the hardest to learn?

28. Are you of the naughty or nice variety?

How often does he play pranks? What if other people don’t like them?

8 Interesting Things to Know About Your Boyfriend

Asking people questions about themselves helps them feel like you are truly interested in them. These interesting questions to ask a guy will send him the message that you want to know all there is to know!

So pick a few and become an expert on your new favorite subject- your guy!

29. What’s something you tried really hard to like but just couldn’t?

Maybe its a food, a sport or a TV show everyone else loved.

30. What are the manliest and least manly things you have ever done?

On a scale of zero to manly, let’s rate things.

31. What are your biggest fears about relationships?

How can you make him more comfortable with those?

32. How many times have you been in love?

Does he feel like that’s not enough? Or too many?

33. What is a relationship deal-breaker for you?

Has it broken up a relationship for him before?

34. Do you believe in monogamy?

If not, what does he think healthy relationships look like?

35. What would you do if your partner became physically disabled?

Would that be too hard to handle? How would he measure?

36. What do you see as ‘couple’s goals’?

Running 5k’s Thanksgiving morning? Coordinating tattoos?

8 Deep Questions to That Will Move Your Relationship Into a More Serious Level

These deep questions to ask your boyfriend will get everyone moving in a more serious direction, stat! Make sure you handle these questions with care - there is a lot of vulnerability being spoken here.

And on that note, don’t be afraid to respond with your own answer. You being open helps create a culture of trust.

37. What is your happiest memory from our relationship?

This would be a good answer to write down and remember.

38. What is your favorite thing about our relationship?

Is it something that comes naturally or something you guys have to work at?


39. Do you think we need to spend more time apart or more time together?

What is the ideal alone/together ratio?

40. Would you risk your life to save mine?

What about someone else? How would he feel about someone sacrificing for him?

41. Do you think relationships are intended to last eternally?

What will they look like after this life?

42. Do you ever feel the need for immense love?

What makes him feel loved, safe, and seen in those moments?

43. Are we significantly less happy in this era of technology?

How can we keep a balance with all of its benefits?

44. What are the two biggest lessons you’ve learned from previous relationships?

Did he learn them the easy way or the hard way?

4 Sexy Questions That Will Help You Be More Intimate With Your Partner

How about some sexy questions to ask your boyfriend that will drive him crazy and possibly get him in the mood to do whatever you want. With these questions, you'll definitely be in control of the situation.

45. What’s your favorite way to be seduced?

Take notes, and use this on him the next time you're in the mood.

46. What's the most sensitive part of your body?

This is definitely a question you already know the answer to.

47. I come home from work stressed, how do you relax me?

Let him show you, rather than tell you.

48. Do you like wearing boxers or briefs?

And tell him which you prefer him to wear, also.

How To Pick The Best Questions To Ask Your Boyfriend

So, there are almost a million questions here, how do you even start? I’ve made a quick little guide to help you make the most of this extensive list of queries.

1. Check your bandwidth

There are times for having deep and probing conversations, and there are definitely NOT times. Make sure you and your guy are in a good space, aren’t having a little spat, not struggling with a big decision, and aren’t tired, hungry, or lonely.

You’ll have the most fun and have better conversations when you’re hearts and minds are open to connecting. Trust me, it’s worth the wait.

2. Pick questions that apply

Don’t just start at the top and start blasting away - some of these questions are more suited to a serious relationship. Don’t scare away a potential partner by asking him to tell you his darkest secret on your first date.

Start slow and easy, and as intimacy builds, feel free to start moving into deeper waters.

3. Be vulnerable and trustworthy

I mentioned it earlier - be open yourself with answering these questions. This shows your guy that you are willing to create a space that is safe for these deep questions!

And be careful with his answers - when he tells you his insecurities or about a happy memory, make sure to thank him for sharing his thoughts, and NEVER use it against him in a fight.

Downloadable and Printable List of Questions to Ask Your Boyfriend

Here is a downloadable and printable List of Questions To Ask Your Boyfriend (right click the image and select Save Image As...):

More Great Ways To Talk to Guys

  1. Maybe you want to use these questions with your boyfriend, but you need a boyfriend first! Start at the beginning and use this helpful list on how to ask a guy out!
  2. Check out our go-to guide on how to flirt with a guy, if you’re looking to add a little playfulness to your dating life.
  3. When you’re wondering, should I text him?, follow this step by step guide to know for sure!

In Conclusion

Now, you have more questions to ask your boyfriend than you know what to do with! Next time you’re trying to remember how to start a conversation with a guy, just break out this handy list and find some great conversation kindling!

Search through the list whenever you think "I wish I had questions to ask my boyfriend". Great conversations are just ahead - have fun!