Starting a conversation with a guy can sometimes feel tricky. Whether you’re just getting to know him, texting late at night, or looking for fun ways to bond with your boyfriend, playing 20 Questions is an easy way to keep things interesting.
This game isn’t just about small talk—it’s about asking the right questions that reveal funny, surprising, and even deep answers. Below, you’ll find 20 questions to ask a guy that range from lighthearted to meaningful, perfect for any setting.
Play the 20 Questions Game Online
Want to make the game even more exciting? Try playing 20 Questions online! Our digital version lets you explore different categories, challenge friends, and discover new ways to keep the conversation flowing.
Whether you’re texting, on a road trip, or hanging out in person, this game is an easy way to connect.
How to Play 20 Questions
Here’s a quick rundown of how the game works. It’s simple, fun, and can lead to some surprisingly interesting conversations.
- One player picks a word or concept. It can be anything—a person, place, or thing.
- The other player(s) take turns asking yes-or-no questions. Each question should help narrow down the possibilities.
- After 20 questions, a final guess is made. If no one figures it out, the person who came up with the word wins!
Now that you know the rules, let’s check out some of the best 20 questions to ask a guy to keep the conversation going!
Fun and Random 20 Questions to Ask a Guy
Want to really get to know a guy? These random and fun 20 questions will help you uncover everything from his guilty pleasures to his weirdest fears. Whether you’re just getting to know him or testing how well you already do, these questions are guaranteed to keep the conversation going.
1. A movie I can quote word for word
Because having a social life is overrated.
2. The weirdest thing I believed as a kid
Some childhood logic just doesn’t hold up.
3. A conspiracy theory I lowkey believe
Maybe they are watching us…
4. My go-to fast food order
A man’s true personality test.
5. The most ridiculous thing I’ve spent money on
Instant regret or a genius purchase?
6. The worst fashion trend I ever followed
Brace yourself for some questionable choices.
7. A food I refuse to eat
Some things just shouldn’t be consumed.
8. A celebrity I irrationally dislike
No reason, just bad vibes.
9. A video game I could play forever
If I disappear for days, this is why.
10. The first job I ever had
A true test of patience and suffering.
11. The weirdest compliment I’ve ever received
Thanks, I think?
12. The most spontaneous thing I’ve ever done
Questionable decision-making at its finest.
13. My worst subject in school
Math? History? All of the above?
14. A song that always hypes me up
Cue the dramatic head bobbing.
15. My most-used emoji
A window into my soul.
16. My guilty pleasure TV show
So bad, yet so addicting.
17. The worst lie I ever told
Did I get away with it? Maybe.
18. The biggest trouble I got into as a kid
Cue the “I’m not mad, just disappointed” talk.
19. A hobby I picked up and immediately quit
At least I tried… kinda.
20. A useless fact I randomly know
Because my brain prioritizes nonsense.
21. The most awkward encounter I’ve had
Secondhand embarrassment is inevitable.
22. My favorite holiday
Free food or presents? Tough call.
23. A weird habit I have
It’s endearing, I swear.
24. The last thing I binge-watched
A deep dive into my latest obsession.
25. My irrational fear
Laugh all you want, but it’s real.
26. The weirdest thing I’ve ever eaten
Did I regret it? Absolutely.
27. My worst haircut experience
We don’t talk about that era.
28. A sport I’m surprisingly good at
Shocking, I know.
29. My go-to comfort food
Because food solves everything.
30. The most embarrassing text I’ve ever sent
Autocorrect betrayed me.
31. A dream job I’d love but probably suck at
Let me dream, okay?
32. The worst advice I’ve ever received
Thanks for nothing, random stranger.
33. A childhood cartoon I still love
Pure nostalgia at its finest.
34. The most random thing I own
No idea why I still have it.
35. The longest I’ve ever stayed awake
A terrible, terrible idea.
36. A weird way I’ve injured myself
Somehow, gravity always wins.
37. My favorite thing to do when I’m bored
Better than scrolling aimlessly, I guess.
38. A meme that describes me perfectly
Basically, my personality in a picture.
39. A fictional character I’d totally be friends with
Please let them be real.
40. The worst date I’ve ever been on
Never again.
41. My favorite smell
Yes, I have strong opinions about this.
42. A ridiculous childhood fear I had
Why was I like this?
43. A song I secretly love but won’t admit
It’s embarrassing, but a banger.
44. My ultimate “hype” song
If this comes on, I’m unstoppable.
45. A celebrity I’d love to grab a drink with
Could be chaotic, could be legendary.
46. My go-to excuse for being late
Totally believable, right?
47. The last thing that made me laugh until I cried
Probably something incredibly dumb.
48. The best gift I’ve ever received
10/10, would cry over again.
49. A reality show I’d absolutely dominate
Move over, contestants.
50. A superpower I wish I had
Realistically, I’d still be late to everything.
51. The weirdest thing I’ve seen in public
Humanity never fails to amaze.
52. My all-time favorite video on the internet
Comedy gold, no explanation needed.
53. The most unexpected compliment I’ve ever gotten
Not sure how to respond to that.
54. A fictional villain I secretly love
Morally questionable but entertaining.
55. A skill I wish I had
In another life, I’m a pro.
56. My worst roommate experience
Living with people is hard.
57. The most unnecessary thing I’ve ever argued about
100% convinced I was right.
58. A random childhood memory that lives in my head rent-free
Why do I even remember this?
59. The most questionable trend I’ve participated in
Regrets? Many.
60. My ultimate comfort movie
Watched it a million times, still not tired of it.
20 Questions to Ask Your Boyfriend
Learn more about your boyfriend in a fun, unexpected way! These random and hilarious 20 questions will put his guessing skills to the test while revealing some of your quirks, favorites, and secret thoughts. Perfect for a date night, road trip, or just a casual chat!
1. The first thing I noticed about you
What made you stand out? (No pressure.)
2. My weirdest comfort food
Normal or just straight-up questionable?
3. The thing I always order at a restaurant
You should know this by now.
4. My least favorite household chore
I’d rather do literally anything else.
5. The last thing that made me cry
Was it a sad movie or just bad customer service?
6. A movie I refuse to watch again
One and done—never again.
7. The pet I’d get if I could
Am I a dog person, a cat person, or something weirder?
8. A language I wish I could speak
So I can finally understand what’s going on.
9. A trend I totally regret following
The cringe still haunts me.
10. The most embarrassing thing I’ve done in public
Let’s just pretend it never happened.
11. My ultimate guilty pleasure song
I hate how much I love it.
12. My favorite way to spend a lazy day
Would I be curled up with snacks or doom-scrolling?
13. A celebrity I’d love to swap lives with
Just for a day, to see how the other half lives.
14. My biggest pet peeve
Prepare for a passionate rant.
15. The one thing I could talk about forever
You might regret asking this one.
16. My favorite childhood toy
Nostalgia overload incoming.
17. A weird superstition I believe in
I can’t explain it, but I know it’s real.
18. The most random thing in my room
No explanation—just vibes.
19. A TV show I’d totally binge again
Some things never get old.
20. My go-to excuse when I’m running late
Totally believable, right?
21. A hobby I’ve always wanted to try
Could I be the next great artist, chef, or… astronaut?
22. The worst advice I’ve ever received
Shockingly bad, yet someone meant well.
23. My biggest irrational fear
Completely ridiculous, but still terrifying.
24. A fashion choice I’ll never make again
The photos are banned from the internet.
25. My most-used emoji
A true reflection of my soul.
26. The best compliment I’ve ever received
Still riding the high from this one.
27. My most iconic childhood injury
A totally avoidable disaster.
28. A dream trip we should take together
Better start packing.
29. A holiday I secretly don’t like
I’m just here for the snacks.
30. The most awkward text I’ve ever sent
Autocorrect, you betrayed me.
31. My favorite smell in the world
Weirdly specific, but amazing.
32. The fictional character I relate to the most
Basically my on-screen twin.
33. A sport I’d absolutely fail at
No athletic ability required—just vibes.
34. My favorite way to annoy you
Don’t lie, you secretly love it.
35. A hidden talent I have
Completely useless but still impressive.
36. The worst haircut I ever had
The trauma is real.
37. My ultimate comfort TV show
Watched it a million times, still not tired.
38. The thing that always makes me laugh
Even when I really shouldn’t be laughing.
39. A phrase I say way too often
I can’t stop, won’t stop.
40. A ridiculous argument I’ve had
And yes, I was right.
41. A food I’d never try, no matter what
Some things are just a hard pass.
42. The most impulsive thing I’ve ever done
Regrets? Maybe. Fun? Definitely.
43. The best birthday I’ve ever had
Top-tier celebration energy.
44. My worst habit
You’ve probably already noticed this.
45. The last thing I bought on impulse
It felt like a good idea at the time.
46. A game I’d definitely beat you at
Let’s settle this right now.
47. A reality show I’d totally win
Move over, contestants.
48. The most embarrassing thing in my search history
Let’s just pretend you didn’t ask.
49. A famous person I’d love to meet
This would either be amazing or so awkward.
50. My dream home must have this one thing
Non-negotiable.
51. The most random thing I’ve memorized
My brain prioritizes the weirdest stuff.
52. A song that will always make me dance
No shame, just vibes.
53. My go-to answer when I don’t know what to say
You’ve definitely heard me say this before.
54. The most chaotic trip I’ve ever taken
Zero planning, maximum fun.
55. A word I can never spell right on the first try
Autocorrect exists for a reason.
56. The best inside joke we have
If you know, you know.
57. The most dramatic thing I’ve ever done
Peak main character energy.
58. A totally useless skill I have
No practical use, but still impressive.
59. My favorite way to procrastinate
I’ll totally start… later.
60. The thing I love most about you
Prepare to be very flattered.
