If you’re tired of the usual “How was your day?” or “What’s for dinner?” and want to add some excitement to your conversations, you’re in the right place. The What If game will have you both laughing, thinking deeply, and maybe even uncovering things you didn’t know about each other.
Whether you’re looking to break the ice or just have a fun, chill night together, “What If” questions will keep the conversation flowing and the laughs coming. It’s like a game, but with your boyfriend at the center, and trust us, it’s going to be a good time.
Ready for some weird scenarios? Let’s dive in!
Play “What If Questions for Boyfriend” Anytime
Looking for a never-ending list of hilarious questions? Perfect for cozy nights in or random moments of fun, these “What If” prompts will keep your boyfriend guessing and you both cracking up.
How to Play What If Questions for Boyfriend
It’s super simple, and so much fun. Here’s how it goes:
Set the mood. Whether you’re on a casual Netflix-and-chill night or looking for something to spice up a dinner date, grab your boyfriend and make sure he’s in a fun mood. The more laid-back, the better!
Ask a What If question. You get to start the game with a random “What If” question. These questions are meant to be totally silly, creative, and wild — the weirder, the better!
For example: “What if you had to live in a world where every time you laughed, you turned into a different animal?”
Share your answers. After you ask your question, give your boyfriend a chance to answer first. Then, you answer next. The key here? The more random and outrageous your answers, the better! No pressure — just let loose.
Pass the turn. After the first question has been answered, it’s his turn to ask the next “What If” question. Keep the game going until your sides hurt from laughing — and maybe until you’ve learned some pretty crazy stuff about each other!
You can end the game whenever you like — or keep going if you’re having a blast. It’s up to you both to decide when the fun is over.
Fun What If Questions for Boyfriend
Curiosity, chaos, and mild emotional damage. These questions will put your boyfriend’s imagination—and memory—through the ultimate relationship obstacle course.
1. What if we swapped phones for a day—what app are you deleting first?
Trust issues: unlocked.
2. If I had to pick your outfit every day, how long ‘til you snap?
Fashion dictatorship incoming.
3. What’s something I do that you pretend doesn’t annoy you?
Tell the truth… gently.
4. If we had to survive on a deserted island, what role would I play?
Spoiler: not the cook.
5. If we had a reality show, what would it be called?
Probably something unhinged.
6. If I challenged you to a dance battle right now, what’s your go-to move?
Bust it—or bust.
7. What if we could never text again—how would you flirt with me?
Carrier pigeon vibes.
8. If your mom had to describe me in one sentence, what would she say?
Careful, you’re being watched.
9. What if I had an identical twin—how would you prove your loyalty?
This feels like a trap.
10. If you had to cook me a romantic dinner using only three ingredients, what’s on the plate?
Chef, don’t fail me.
11. What’s one moment with me you replay in your head when you miss me?
Cheesy but necessary.
12. If we switched bodies for a day, what would you do first?
Think before you answer.
13. If I asked you to write me a love song, what would the chorus be?
Taylor Swift, who?
14. What if you could give me one superpower—what would it be?
Useful or purely chaotic?
15. What’s one lie you’ve told me that you’re ready to confess?
Now’s your chance.
16. What if I started a podcast—what would it be about?
Chaos, opinions, or us?
17. What’s your weirdest dream involving me?
Please keep it PG-ish.
18. If you could relive one of our fights just to win it, which one are you choosing?
Petty king behavior.
19. What if I told you I could read your mind?
Scared? You should be.
20. If we could teleport anywhere right now, where are you taking me?
Romantic or random?
21. What’s one thing I do that makes you feel ridiculously loved?
Sappy time activated.
22. What if your friends were secretly rating me—what score do I get?
Choose wisely.
23. If we were both stranded on a road trip, who’s freaking out first?
Not me, obviously.
24. What’s something you hope I never change about myself?
Aww, cue the tears.
25. If I were an app on your phone, which one would I be?
Bonus points for chaos.
26. If I were a video game character, what would my power-up be?
Girlboss or gremlin?
27. What if we could only speak in inside jokes—how screwed are we?
Comms breakdown imminent.
28. What’s one topic you know better than me—but I act like I don’t care?
Ego check moment.
29. What would your ex be most shocked to know about our relationship?
Name drop optional.
30. If I had to choose your next tattoo, what would I make you get?
It’s giving permanent regret.
31. What’s the most irrational thing I’ve ever gotten mad about?
Let’s unpack it.
32. If I became a famous celebrity, what scandal would I be involved in?
PR nightmare unlocked.
33. What’s one thing you’d do more of if I wasn’t around to judge?
No judgment (yet).
34. If you were a rom-com boyfriend, what cliché would you totally nail?
Rain kiss? Jealous speech?
35. What if we had to be completely honest for 24 hours—how much trouble would you be in?
Dangerous territory.
36. If I had a secret double life, what would it be?
Spy? Stripper? CEO?
37. What’s something you think I believe, but you’ve never actually asked?
Assumptions are wild.
38. What’s one song lyric that instantly reminds you of me?
Sing it or it doesn’t count.
39. If I had to delete one social media app forever, which one are you saving for me?
Pick my poison.
40. What if I had amnesia and forgot we were together—how would you win me back?
Plot twist potential.
41. What’s one secret thought you’ve had mid-makeout with me?
Go on, brave soul.
42. If I got super famous, how would you handle the fangirls?
Supportive or stressed?
43. What’s something you lowkey flex about when you talk about me?
Bragging rights engaged.
44. What if I could hear your internal monologue—how shocked would I be?
Yikes or swoon?
45. If I was a red flag, which one would I be?
Tread lightly.
46. What if we could only communicate via voice notes—how long ‘til I dump you?
Better warm up your mic.
47. What’s one habit I have that you secretly copied?
Caught in the act.
48. If you were designing a dating app just for me, what’s the tagline?
“Loves chaos and cuddles”?
49. What if I started every sentence with “my love language is…”—how long until you snap?
Sweet, but threatening.
50. What’s something you want to tell me but don’t know how to say?
Say it with chest.
51. What if we woke up married in Vegas—what’s our first move?
Panic or party?
52. If I turned into a dog for a week, how would you take care of me?
Walks, treats, or chaos?
53. What’s your biggest ick about me that you now secretly find adorable?
Rude but real.
54. If I wrote a fanfic about us, what would the plot be?
Enemies to lovers, probably.
55. What if we could only see each other in dreams—what’s your first move?
Lucid love affair.
56. What’s one thing I do that makes you question your sanity—but you let it slide?
Love is blind.
57. If we could only kiss during commercials, what show are we watching?
Choose wisely.
58. What’s something you hope we laugh about when we’re 80?
Bonus if it’s cringe.
59. What if I asked you to delete your entire playlist and make one for us—what’s song one?
No pressure, DJ.
60. What’s your favorite version of me—silly, sad, sleepy, or savage?
There is a right answer.
Naughty What If Questions for Boyfriend
Things are heating up. Not safe for family gatherings… or your group chat.
1. Ever thought about doing it somewhere we absolutely shouldn’t?
The riskier, the better.
2. Which part of my body do you secretly obsess over?
No pressure, but there’s a right answer.
3. What’s your dirtiest dream that you still haven’t told me?
Don’t act innocent now.
4. If we were caught in the rain, would you kiss me or undress me?
Choose wisely.
5. Would you rather be teased for an hour or take full control for five minutes?
Endurance test, incoming.
6. Ever wanted to be watched?
Your exhibitionist is showing.
7. How would you seduce me if we were strangers at a party?
Smooth talk or chaotic flirting?
8. What roleplay would you actually want to try?
No judgment—only props.
9. If I gave you a free pass to do anything to me for one night, what would happen?
Be specific. Very specific.
10. Are you more into being praised… or punished?
There’s a fine line.
11. Where would you kiss me if you couldn’t kiss my lips?
Think outside the box. Or inside.
12. How long could you last if I was teasing you nonstop?
Time to test your stamina.
13. What’s the most sensitive spot on your body?
Don’t pretend you don’t know.
14. Describe exactly how you’d undress me.
No skipping steps.
15. What do you want me to whisper in your ear next time I touch you?
Whispers lead to wicked things.
16. What’s one thing you’ve always wanted to try but haven’t told anyone?
Today’s the day.
17. Do you prefer it rough, slow, or somewhere in between?
Goldilocks, but make it dirty.
18. How do you feel about handcuffs… asking for a friend.
Not that innocent.
19. Spit or swallow—your opinion?
Let’s just talk logistics.
20. Ever had a praise kink or a degradation kink moment?
Duality is hot.
21. Where’s the most public place you’d hook up with me?
The bolder, the better.
22. Would you sneak off with me at a party for a quickie?
Don’t act shy now.
23. How would you handle me whispering something filthy in your ear at dinner?
Please don’t knock over your drink.
24. On a scale of 1–10, how into public teasing are you?
Let’s raise the bar.
25. If we got caught making out in an elevator, how would you play it cool?
Bonus points for confidence.
26. What’s one thing you’ve always wanted me to say in bed?
I’m taking notes.
27. Do you want me to moan your name or beg for more?
Only one’s an ego boost.
28. How would you dirty talk me if we couldn’t touch?
Put that imagination to work.
29. Ever fantasized about me talking you through exactly what I’m going to do?
Spoiler: it’s happening soon.
30. Say the filthiest sentence you can come up with right now.
Make me blush.
31. Would you rather tie me up or be tied down?
Choose your position.
32. How would you take control if I said “do anything you want”?
And I mean anything.
33. If I begged you to stop but didn’t mean it, how would you know?
Trick question?
34. Ever wanted to fully submit to me for a night?
Yes, queen.
35. What’s your ultimate power move in bed?
Your signature dish.
36. Be teased with zero touching for 30 minutes or go straight into it but no foreplay?
Painfully hard choices.
37. Watch or be watched during sex?
Pick your poison.
38. Lingerie or naked under a trench coat?
Visuals matter.
39. Quickie in the morning or marathon at night?
Coffee or cardio?
40. My hands tied or your hands tied?
Fair is fair.
41. Have you ever thought about filming us?
Lights, camera, consent.
42. Is there a kink you’re lowkey embarrassed to admit you’re into?
Spill it—we’re grown.
43. Would you go to a sex club with me just to watch?
Or participate…?
44. Ever fantasized about me being jealous while someone flirted with you?
Toxic? Maybe. Hot? Also yes.
45. Would you want me to take nudes of you?
Equality, baby.
46. Describe our sex life like it’s a movie trailer.
Blockbuster vibes only.
47. Pick a theme song for our next hookup.
Bonus points for lyrics.
48. What outfit would you love to see me in—if I wasn’t planning on wearing it long?
Style meets stamina.
49. What would your porn star name be?
Now hiring.
50. Name a scene we should totally recreate.
And go full method acting.
51. Have you ever faked it? 👀
We can handle the truth.
52. What’s something I do in bed that drives you absolutely wild?
Let me keep doing it, pls.
53. What do you fantasize about during boring days?
Don’t say spreadsheets.
54. What’s the one thing you wish we did more?
Say the word.
55. What does your dream night with me look like—start to finish?
Set the mood.
56. Describe how you’d undress me with just your eyes.
Use detail. Lots of it.
57. What turns you on instantly—no matter what?
That switch better flip fast.
58. What’s the hottest thing I’ve ever said to you?
Let’s repeat it later.
59. What would you do if I told you I wasn’t wearing anything under this?
Keep your cool… or not.
60. What’s your favorite sound I make in bed?
Yes, this is a trap.
61. Do you think we’re compatible in bed—or too compatible?
Too hot to handle?
62. What’s one thing we do that no one else could give you?
Let’s protect that energy.
63. Would you rather wake up to me or fall asleep beside me after?
Soft boy moment unlocked.
64. If we made a “best of us” list… what moment’s at the top?
The highlight reel.
65. What do you love most about how I touch you?
We’re ending on a high note.
66. Would you write smut about us?
Start with “It was a dark and stormy night…”
67. Could you handle being my submissive for 24 hours?
No backtalk allowed.
68. What’s one toy you secretly want to try?
Don’t worry—I’ll add it to cart.
69. Would you rather do it in the shower, the balcony, or the backseat?
Classic chaos.
70. What’s your wildest sex bucket list item?
If it’s not a crime, let’s talk.
