There’s a special kind of boredom that only happens in love. You’ve watched all the shows, you’ve ordered the food, and now… you’re just staring at each other like two cats waiting for something to happen. That’s the moment when weird questions become magic.
Asking offbeat, unexpected questions is one of the best ways to turn silence into laughter and make your boyfriend look at you like “How did I fall for this adorable weirdo?”
These aren’t your usual “what’s your favorite color?” kind of questions. These are the “what if I was secretly a squirrel spy?” kind of questions.
So if you’re in the mood to get weird, playful, and just a little chaotic (in the cutest way), this list is for you. Copy, paste, ask, and prepare for answers that make boredom run for cover.
If I turned into a squirrel and started stealing snacks from your kitchen, would you still date me?
What animal do you think I was in a past life — and why is it something weird?
If we had to live in a house made entirely of cheese, how long would we survive?
Would you rather fight 100 duck-sized versions of me or one horse-sized version of me?
If I had a pet ghost who was jealous of you, what would you do?
Which vegetable would be the sassiest if it could talk — and would it like me?
Would you still love me if I could only speak in pirate language?
If I got abducted by aliens but they returned me because I talk too much, how offended would you be?
If I randomly started walking like a crab, would you walk beside me or pretend not to know me?
What would be your first move if we woke up one day and swapped bodies?
If I joined a cult that worshipped waffles, would you join or stage a dramatic rescue?
Would you rather I had spaghetti hair or marshmallow feet?
What weird superpower do you think I secretly have but hide really well?
If I had to wear a chicken costume every Friday, would you match me or walk three feet away?
Would you still date me if I insisted on narrating my life in dramatic voiceovers?
If I challenged you to a staring contest with no blinking allowed, how competitive would you get?
Would you rather I laugh like a hyena or sneeze glitter for the rest of our lives?
If I could teleport but only to fast food restaurants, which one would we live near?
What would you do if I just randomly turned into a toaster for 24 hours?
Would you eat a bowl of cereal with ketchup if I dared you to… for love?
If we had to wear matching onesies everywhere for a week, what would they look like?
What conspiracy theory would I start just to annoy you?
If I suddenly decided to start communicating only via interpretive dance, would you learn to translate?
Would you still kiss me if I had permanent spaghetti sauce on my face for some reason?
If I grew a third eyebrow, would you pretend not to notice or name it?
Which part of me would aliens be most confused by?
What weird animal duo best describes our relationship and why?
If I built a blanket fort and refused to come out, how would you convince me?
Would you join me in a two-person flash mob in the middle of a grocery store?
If we opened a restaurant with only one item on the menu, what ridiculous thing would it be?
If my laugh suddenly sounded like a duck honking, would you record it or run away?
Would you rather I had tiny dinosaur arms or one very long sloth arm?
If I believed I was secretly a potato, would you support my journey?
What strange habit do you think I’d have if I lived in medieval times?
If I became internet famous for something super weird, what would it be?
If you had to describe me using only kitchen utensils, what would I be?
Would you let me give you a makeover… blindfolded?
If my evil twin showed up and tried to steal you, how would you know it wasn’t me?
What would you do if I meowed randomly every time you said the word “love”?
If I insisted on calling you “Captain Snugglepants” in public, would you go along with it?
Would you rather I whisper everything like a spy or shout everything like a TV host?
If my shadow started moving differently from me, would you still hold my hand?
What would you do if I woke up one day convinced I was a pigeon?
If we could only communicate through interpretive food art, what’s the first meal you’d send me?
Would you help me build a time machine powered by chocolate and sarcasm?
How to Ask These Weird Questions (and Make It Even More Fun)
Weird questions are already half the fun but how you ask them can take things to a whole new level of playful chaos. Here are a few ways to make your Q&A moments unforgettable:
1. Turn it into a mini game
Write down your favorite questions on slips of paper and put them in a jar. Pull one at random whenever you’re bored, stuck in traffic (as passengers, of course), or lounging on the couch. It’s like truth-or-dare… but weirder and 100% cuter.
2. Use voice notes for dramatic effect
Try recording yourself asking one of the silliest questions with your most serious voice, bonus points for fake accents or dramatic music in the background. Send it and wait for the confused emoji reactions.
3. Pick a “question of the day”
Send him one of these each morning or night, not just for laughs, but to keep the vibe light and spontaneous. He’ll start looking forward to it more than his morning coffee.
4. Ask in the middle of something totally normal
Nothing’s funnier than dropping “If I turned into a squirrel…” mid-way through watching a documentary or folding laundry. The weirder the timing, the better the reaction.
5. Make it a challenge
Tell him: “You can’t laugh or smile while answering this question.” Spoiler alert: he’ll fail. And you’ll win.
6. Let his answers inspire inside jokes
Once he gives a hilarious answer, own it. If he says you’d be a “talking pineapple with trust issues,” then guess what, that’s your new alter ego. These jokes grow into tiny love codes that no one else understands.
Weird questions aren’t just weird. They’re playful ways of saying “I like you so much, I want to know how you’d react if I turned into a potato.”
And let’s be real, if he sticks around after question #19, he’s a keeper.