40 Random Questions to Ask Your Boyfriend

By on September 28, 2014

Whether you’re in a serious long-term relationship or just hooking up for you third date, finding stuff to talk about can be difficult. And you don’t want to throw a conversation topic out there only to find it can be resolved with a few yes or no answers, or some shrugging and nodding. You want something that’s going to delve into your very hearts and souls, and bring you closer as a couple and, truly, a pair of human beings. But hey, you’ll also settle for something new and kinda funny. Fear not, for we have brought a range of questions, both personal and general, and hilarious and must-know. Never suffer in awkward silence alone again (especially if you print this page and keep it on you at all times, which I totally recommend that you do.

 random questions to ask a guy

1. What’s the stupidest things you’ve ever done?

stupid thing

Nothing bonds a couple like cringing over moments that you’d buried at the back of your head, never to be looked at again. Nothing.

2. Who is your biggest celebrity crush?


A chance for your boyfriend to rant about how beautiful Jennifer Lawrence is on your behalf? Um, yes.

3. What’s the worst nickname you’ve ever had?

See number one: just try to remember not to use it at an importune moment in the future lest you bring back childhood blushes.

4. Where would he love to travel?

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Everyone has a secret place that they’d love to take a hike to- find out his. Then plan the trip.

5. If you could play one instrument, what would it be?


Everyone has had visions of themselves rocking out with their imaginary band and their smash hit single, but not everyone plays the same thing in their fantasies. Would he be a brooding guitarist or a showy lead man?

6. What’s the weirdest food you’ve ever eaten?

weird food

Bring back either a bunch of disgusted cringes or a browse through local restaurants who might be able to satisfy your cravings.

7. How would you spend a million bucks in one day?


Is he a make-investments kind of guy or a buy-the-sports-team kind of guy? Know for certain either way, and reap hints for your own inevitable windfall.

8. What was the last film you saw that made you laugh?

comedy film

This is actually a harder question that it first seems, if you ignore polite chuckles in the cinema. And find out how good/bad his taste in comedy is.

9. What’s your perfect pet?


You genuinely need to know if he’s a cat person or a dog person. These are the real questions that need answering in relationships.

10. What’s the worst holiday you’ve ever been on?

Awful holidays are a leveller for every single person in the world, and maybe yours will seem awesome by comparison. Doubt it, though.

11. Which city would you most like to live in?

beautiful city

Work out his tolerance for arts, culture, and parks of every description. Again, these are need-to-knows for your relationship.

12. What’s your dream job?

dream job

And we mean childhood dream- what crazy candy-fuelled fantasy job did he imagine he’d one day have when he was a grown-up? Bonus points if he’s already doing it.

13. What’s his favourite meal?

This can be anything from a guilty pleasure of junk and goodies to the poshest of the posh menus in the highest-class eaterie in the city.

14. What’s your favourite book?

Not enough people read enough any more. Bring booksack to the table, and find out what he was forced to read in high shchool (or maybe even beyond!).

15. What would your gameshow specialist subject be?

Everyone secretly has a passion that they know way too much about. Which one would he put to use in the pursuit of cold, hard cash and television screentime?

16. When was your first kiss?


Whether he got a peck from a girl in kindergarten or had his first awkward smooch in high school, first kiss stories are usually adorable or super awkward. Basically, fun either way!

17. What tattoo would you get if you had to get one?


Even if he’s already got tats, finding out what else he’d have permanently drawn onto his body is always an interesting talking point.

18. What was your worst subject at high school?

Whatever high-flying job you and he are both working now, everyone had their secret shame subject when they were enduring those four brutal years.

19. Would you ever consider doing an extreme sport? If so, what?

bungie jump

Whether he’s the furthest thing from an adrenalin junkie or not, would he be jumping out of a plane or bungee jumping off a bridge?

20. What was the most nerve-wracking experience of your life, that ended up turning out okay?

If it was a job interview or a prom proposal, find out what really had him squirming- before he came out on top, of course.

21. What album defined your teens?

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Everyone need their dose of angst as they hit those turbulent years, and some of us hold those albums in the highest esteem-or deepest shame.

22. What was the last TV show you watched from start to finish?

tv show

Whether he’s been keeping up with True Detective or getting down with Hannibal, something about that little box will tempt us all.

23. What’s the one piece of technology you wish would hurry up and get invented already?

Even if he wasn’t raised on Back to the Future, he’ll know whether he’d want a hoverboard or a lightsaber.

24. What movie can you just not stand?

It might be a guilty pleasure, a mindless action flick, or a cheesy romcom- but everyone diverts from the mainstream somewhere. Where’s his movie limit?

25. Which band would you most like to go and see live?


Whether their still together or not, find out if his dream ticket is somewhere in the realm of Nirvana or closer to Fall Out Boy. Judge accordingly.

26. What habit do you find most annoying?

bad habits3

Nail-biting, hair-playing, seat-shifting….everyone has their one bugbear that just makes their teeth grind (which is also totally annoying).

27. What’s your musical guilty pleasure?

Have you found suspect CDs hiding at the back of their wardrobe? Bring their secret shame out into the open once and for all.

28. What kid’s movie secretly still appeals to you?

back to the future

Was he a Disney boy or a cool Karate Kid- kid? Reminisce about those lost treasures of childhood that you secretly want to rediscover.

29. What rules did you break as a teenager?

Everyone has a story about how they defied authority in their teens- whether it was skipping class or jumping curfew, let them atone for their sins.

30. What’s the coolest way you’ve ever spent a night out?

night bar

Hitting up bars in Europe or hiking up a mountain at midnight….recounting a treasured memory is an awesome way to bond, and find out what he’s into.

31. What stereotype do you find really annoying?

Whether it’s men being lazy slobs or women being uptight, shoe-obsessed maniacs, there’s one stereotype that makes everyone roll their eyes and switch the channel.

32. What one song sums up your life right now?

listening music

Everyone looks out the window of a car with their headphones in at some point, pretending to be in a music video for this song that just sums up everything. What’s his?

33. What’s the strangest way you ever met a close friend?

Staggering through nights out or finding refuge in a work conference, there’s one friend who’s origin story you always like to tell again.

34. Are you a morning person or a night person?

night life

Do they find themselves up with sun? And if so, are they just heading to bed or just jumping out of it?

35. What’s the strangest dream you’ve ever had?

strangest dream

There’s always one particularly vivid or strange dream that hangs around the back of your head for months after you’ve woken up, and there must be a screenplay in their somewhere.

36. Who is your favourite sitcom character?

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Are they a Frasier buff or a Modern Family aficionado? Find out who they secretly relate to, and who they wish they really were.

37. What’s your go-to dance move?

Admit it: you’re picturing yours right now. When they hit the dancefloor, what move to they immediately start rocking out? And how impressive is it, really?

38. What’s the funniest story you’ve ever heard?


It might have developed into a rather larger tale than was originally woven, but hearing a wild tale of hilarity and hi-jinks is sure to be at least mildly amusing.

39. What TV show would you want to create?

Is it  comedy-reality show about him and his friends, or a gritty crime drama (with him and his friends)? Everyone should have put thought into this at some point.

40. What food do you always find yourself craving?

craving food

Hopefully, it’ll be some shamelessly weird and crazy creation that you’re just going to have to try out at some point.


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