Not sure what to ask when you’re getting to know a girl? The 20 Questions game to ask a girl is the perfect way to break the ice and keep the conversation flowing. Whether you’re just friends, on a date, or texting your crush, the right questions can make all the difference.
From lighthearted and funny to deep and thoughtful, these 20 questions to ask a girl will help you learn more about her in a fun and casual way. Plus, if you’re looking for 20 questions to ask your girlfriend, we’ve got some great ones that’ll bring you two even closer!
Play the 20 Questions Game Online
Want to make things even easier? Try our 20 Questions game online! It’s a quick and exciting way to play with friends, your girlfriend, or even new people you meet. With tons of categories and creative prompts, you’ll never run out of things to ask.
How to Play 20 Questions
Before we get into the best questions, here’s a quick refresher on how to play:
- One person thinks of something. It could be a person, place, thing, or even an abstract idea.
- The others ask yes-or-no questions. These questions help narrow down the possible answers.
- Guess before 20 questions are up! If someone guesses correctly, they win! If not, the person who picked the item wins.
Now that you know the rules, let’s jump into the best 20 questions to ask a girl!
Fun & Random 20 Questions to Ask a Girl
Some questions are cute, some are chaotic, and some will make her question why she’s even talking to you. But that’s the fun of the 20 Questions game to ask a girl—it keeps things interesting. Whether you’re playing on a road trip, at a party, or just passing time, these random and fun 20 questions to ask a girl will get the conversation going.
1. A song I secretly love but would never admit
Is it embarrassing? Probably.
2. My childhood dream job
Astronaut, pop star, or something totally random?
3. A food I irrationally hate
It’s not my fault, okay?
4. My biggest guilty pleasure
Something totally cringe but I love it anyway.
5. A reality show I’d totally win
Drama, competition, or both?
6. The worst fashion trend I ever tried
Regret level: 10/10.
7. A fictional character I’d date in a heartbeat
Yes, I have a type, and yes, he’s animated.
8. My go-to comfort movie
Something wholesome or weirdly specific?
9. The most spontaneous thing I’ve ever done
Did it end well? Unclear.
10. My biggest irrational fear
No, it doesn’t make sense, but here we are.
11. A hobby I always say I’ll try but never do
It’s the thought that counts, right?
12. The last thing I Googled
Might expose my entire personality.
13. My most embarrassing childhood moment
Let’s pretend this never happened.
14. A trend I will never understand
Seriously, why is this a thing?
15. My signature dance move
It’s iconic (in my head).
16. Something I spend way too much money on
No regrets. Okay, maybe a little.
17. My go-to order at a coffee shop
Sugar? Caffeine? Both?
18. A conspiracy theory I lowkey believe
Not saying it’s true… but what if?
19. My worst cooking fail
Fire alarms may or may not have been involved.
20. The one emoji I overuse
I have no control over this.
21. A language I wish I could speak fluently
For travel, flexing, or just yelling dramatically?
22. The first celebrity crush I ever had
Prepare to judge me.
23. A skill I wish I magically had
If only I could wake up talented.
24. The weirdest compliment I’ve ever received
Flattered? Confused? Both.
25. A childhood game I was weirdly good at
This was my Olympic sport.
26. Something that instantly makes me laugh
It works every time.
27. My most-used phrase or catchphrase
Unintentionally part of my personality now.
28. A piece of clothing I’d never be caught wearing
No amount of money would convince me.
29. The last show I binged way too fast
Did I even blink?
30. My most unnecessary talent
Completely useless, but impressive.
31. A scent that instantly makes me happy
It’s probably something oddly specific.
32. My most ridiculous pet peeve
Yes, it annoys me, and yes, I know it’s dumb.
33. The worst haircut I ever had
Still recovering emotionally.
34. A childhood belief I refused to let go of
Embarrassing but kind of adorable.
35. The best prank I ever pulled (or fell for)
Chaos levels: high.
36. The one item I’d bring to a deserted island
Priorities matter, okay?
37. A fictional world I wish was real
Because reality is overrated.
38. The weirdest thing I’ve ever eaten
Not proud of this moment.
39. My most dramatic overreaction
10/10 Oscar-worthy performance.
40. A song that always makes me emotional
Tears = guaranteed.
41. Something people always assume about me (but it’s wrong)
Please, allow me to correct you.
42. A childhood toy I was obsessed with
No shame, just nostalgia.
43. My ideal lazy day plans
It involves zero effort.
44. The last lie I told (probably harmless)
Totally innocent, I swear.
45. The one thing I refuse to share
Mine. Forever. No exceptions.
46. My worst texting habit
I swear I’m not ignoring you.
47. A fictional villain I kinda love
Look, they had a point.
48. The weirdest thing I do when I’m alone
Let’s pretend this is normal.
49. My worst ‘sleep talking’ moment
Yes, I’m unhinged even in my sleep.
50. The most dramatic way I’ve ever quit something
Main character energy.
51. A childhood fear I still have
Grown-up? Barely.
52. A moment that made me cringe years later
Thinking about it keeps me up at night.
53. The best compliment I’ve ever received
I’m still holding onto it.
54. My go-to way to get out of an awkward situation
Disappear? Change the subject? Fake a call?
55. The most ridiculous dare I’ve ever done
Would I do it again? Maybe.
56. A slang term I use way too much
It’s a personality trait now.
57. The most spontaneous purchase I’ve ever made
Impulse control? Never heard of it.
58. My ideal karaoke duet song
Serious? Silly? Full-on power ballad?
59. A fictional sidekick I’d want in real life
Every main character needs one.
60. My dream superpower (and how I’d totally misuse it)
Let’s be real—I wouldn’t use it responsibly.
60 Fun and Random 20 Questions to Ask Your Girlfriend
Want to get to know your girlfriend in the most entertaining way possible? These random and fun 20 questions will help uncover everything from her quirks to her secret dreams. Whether you’re just starting out or have been together for a while, these questions will make for some hilarious, deep, and unexpected conversations!
1. If I could time travel, where would I go?
Would I rather see dinosaurs or vibe in the ‘80s?
2. The weirdest thing I believed as a kid
Spoiler: It’s probably really embarrassing.
3. A conspiracy theory I lowkey believe in
I swear, it all makes sense if you think about it.
4. My go-to comfort TV show
The one I rewatch instead of starting something new.
5. The most irrational fear I have
It might be completely ridiculous, but it’s valid.
6. My guilty pleasure snack combo
Would Gordon Ramsay judge me? Absolutely.
7. Something super random I’m good at
A talent no one asked for, but here it is.
8. If I were an animal, what would I be?
This is basically my spirit guide.
9. The most impulsive thing I’ve ever done
Regrets? Maybe. Fun story? Absolutely.
10. A food I cannot stand
You’ll never catch me eating this. Ever.
11. My biggest “ick” in a person
Yes, it’s that serious.
12. A song that describes my personality
Am I an indie ballad or a chaotic pop anthem?
13. The weirdest dream I’ve ever had
Get ready for an unhinged bedtime story.
14. My most used emoji
It says everything about me.
15. If I could switch lives with anyone for a day
Would I go rich and famous or just super chill?
16. The one thing I could talk about forever
Prepare for a passionate rant.
17. My most embarrassing childhood phase
Braces? Cringe outfits? You’re not ready for this.
18. If I had a reality TV show, what would it be about?
It’s giving high drama or absolute chaos.
19. The most ridiculous argument I’ve ever had
It was dumb. I was committed.
20. A fictional character I have a crush on
Yes, they’re not real. Yes, it still counts.
21. A skill I wish I had
Imagine how cool I’d be if I could actually do this.
22. The most unexpected compliment I’ve ever gotten
I still think about it way too much.
23. If I had to eat one meal forever
Would I survive on just this? Absolutely.
24. A TikTok trend I secretly love
Yes, I’ve probably tried it. No, there’s no evidence.
25. My favorite smell in the world
It’s oddly specific, but it makes sense.
26. If I could only shop at one store forever
You’ll know exactly where to find me.
27. The most unnecessary purchase I’ve ever made
It made sense at the time.
28. If I could swap lives with a celebrity
Who gets to live my life while I take theirs?
29. The worst advice I’ve ever received
And why I definitely didn’t listen.
30. My dream job as a kid
Spoiler: It probably didn’t happen.
31. If I were a drink, what would I be?
Classy cocktail or chaotic energy drink?
32. A movie I refuse to watch
Nope. Not happening. Ever.
33. My most chaotic habit
It’s endearing… or maybe just slightly concerning.
34. The most extra thing I’ve ever done for someone
10/10 effort. 2/10 logic.
35. My go-to lie when I don’t want to go out
Classic, effective, and believable.
36. If I could invent a holiday
It would be ridiculous, but necessary.
37. The first thing I’d do if I won the lottery
Chaotic splurge or responsible investment? (Probably both.)
38. A trend I’ll never understand
It happened. I’m still confused.
39. My ultimate dream vacation
Somewhere fancy, fun, or just full of snacks.
40. The most awkward thing I’ve ever said
To this day, I cringe thinking about it.
41. The most random thing I carry in my bag
No explanation. Just vibes.
42. If I could live in any decade
Would I thrive in the ‘70s or struggle in the ‘20s?
43. The weirdest compliment I’ve ever received
Strangely specific, but appreciated.
44. The one app I couldn’t live without
Yes, it’s embarrassing. No, I won’t change.
45. If I could be any Disney villain
I’d be iconic and so dramatic.
46. The most hilarious misunderstanding I’ve ever had
Pure chaos. Zero context.
47. The one thing I always forget
It’s a daily struggle.
48. If I had to rename myself
Would I pick something cool or completely unhinged?
49. The most ridiculous thing I’ve ever cried over
In my defense, it felt serious.
50. The last thing I googled
Absolutely exposing myself with this one.
51. If my life were a rom-com
Would it be cute or just an absolute mess?
52. A weird habit I have when I’m alone
Do I even realize I do this? Nope.
53. The worst advice I’ve ever given someone
I meant well. It backfired.
54. The most random fact I know
It will never be useful, but here we are.
55. The first thing I’d do as a ghost
Would I be spooky or just petty?
56. My most iconic childhood Halloween costume
It was a choice.
57. The thing I’d want to be famous for
Would I be an icon or a meme?
58. The most ridiculous dare I’ve ever done
Regrets? Maybe. Fun memory? Definitely.
59. The one thing I can’t stop buying
No self-control. No regrets.
60. My biggest ‘main character’ moment
Was I extra? Absolutely.
These 20 questions will definitely keep things interesting! Whether you’re laughing over old memories or realizing your girlfriend lowkey believes in mermaids, this list is guaranteed to spark some fun, weird, and deep convos.
