Sometimes love speaks in roses and candlelight. Other times, it sounds like “Would you still date me if I was a worm?”
Let’s be honest, one of the best ways to deepen your connection is to laugh together. That means swapping serious talks for cheeky questions that make your boyfriend smirk, giggle, or pretend to be annoyed while secretly loving the attention.
If you’re looking for flirty fuel to turn your next date night or lazy Sunday into a sweet (and slightly chaotic) Q&A session, these questions are exactly what Cupid would’ve written in his notes app. Think of them as tiny sparks, lighthearted, a little mischievous, but full of heart.
Whether you’re snuggled up on the couch or texting across time zones, these romantic questions to ask your boyfriend to make him laugh will help you both crack up and maybe even fall a little harder.
Would you still love me if I turned into a frog every night at midnight?
If we were characters in a romantic comedy, what would our most dramatic scene be?
What’s your go-to “I’m trying to be cute” face? Show me.
If I stole all your hoodies, what would you do about it?
Would you let me win in a pillow fight, or would you fight like it’s the Olympics?
What do you think I dream about when I’m sleeping next to you?
If I was a cat, would you still date me? And would you clean my litter box?
What’s your secret “awww” moment with me that you’d never admit to your friends?
Which one of us would survive longer in a zombie apocalypse? Be honest.
Would you rather kiss me every morning or every night… or both?
If I was a dessert, what would I be? And how quickly would you eat me?
Have you ever tried to act cool in front of me but totally failed?
What’s something totally random I do that you secretly find adorable?
Would you carry me like a princess if I pretended I twisted my ankle?
If I made you a terrible dinner, would you fake loving it or order pizza?
What’s your “I miss her” behavior when I’m not around?
If we were in a cartoon, which characters would we be and why?
Would you rather have unlimited kisses from me or unlimited pizza?
How many selfies with me is too many? Trick question.
Would you let me draw a mustache on you while you sleep… for science?
If I was a villain in a movie, would you still root for me?
What’s something I do that always makes you laugh, even when you try to resist?
If you had to rename me based on my personality, what name would you pick?
Would you rather be stuck in an elevator with me for 24 hours or with your favorite celebrity for 1 hour?
What’s your silly pet name for me that you’ll never say in public?
Can you describe our relationship using only emojis?
If we switched roles for a day, what’s the first thing you’d do as me?
Would you still date me if I spoke in rhymes for 24 hours straight?
What was your first *“oh no, I really like her”* moment?
If you had to make a rap about our love story, what would the chorus be?
Would you rather tickle me for 5 minutes or be tickled for 5 minutes?
How many kisses would you trade for one of my fries?
What’s your guilty pleasure when it comes to us?
If we had a couple theme song, what ridiculous genre would it be in?
Would you rather relive our first date forever or live one random date from the future?
How long could you last without texting me something cute?
If I was an alien, would you help me blend in or expose me for the clout?
If we had a “couple costume” every day, what would today’s be?
Would you let me be your phone wallpaper even if I looked goofy in the photo?
If love was a sport, what position would you play?
What’s your “pretending not to miss me” tactic?
How dramatic would you be if I stole the blanket at 2am?
If you had to write a movie about our love, what would the ridiculous plot twist be?
Would you rather go on a fancy date or a chaotic one where we just wing everything?
What’s the one thing I do that makes your heart laugh?
Would you still love me if I had a laugh that sounded like a cartoon duck?
Can you impersonate me when I’m being extra affectionate?
If I challenged you to a slow-motion staring contest, who would win?
What’s the cheesiest thing you’ve ever thought about me but never said out loud?
Would you rather hug me for one hour or kiss me for five minutes?
If we had a couple mascot, what animal would it be and what’s its name?
What’s your imaginary plan to propose to me if it had to involve glitter and goats?
If I could read your mind for one minute, what would I catch you thinking about me?
Would you survive if I took over the TV remote for a week?
If we made our own romantic holiday, what weird tradition would it have?
Would you rather get a tattoo of my name or wear matching unicorn onesies in public?
What’s something ridiculously small I do that secretly melts you?
How jealous would you be if another dog liked me more than you?
If we had to live in a rom-com world, which couple trope would we be?
Would you let me win at video games if I gave you a puppy-dog look?
10 Questions That Deserve a Closer Look
Some questions are just too good to scroll past. They spark laughter, invite cheeky answers, and sometimes even pull out the softest, most unexpected confessions.
Below are ten of our favorites, complete with playful explanations and little tips on when and why to ask them. These aren’t just conversation starters, they’re secret doors into his goofy, lovable brain
1. Would you still love me if I turned into a frog every night at midnight?
This one’s pure fairytale chaos. It’s adorable and ridiculous, which is why it works so well. Asking this is like saying “Will you love me no matter how weird I get?” without actually saying it.
The best part? His answer might involve magical kisses, swamp adventures, or frog pajamas. Use this when you’re being silly, clingy, or just fishing for a love confession disguised as a joke.
2. What was your first “oh no, I really like her” moment?
This question will always lead to a soft, smitten answer. It brings him back to that exact moment when he realized you weren’t just “someone,” you were the someone.
Whether it was your laugh, a random text, or the way you order fries, the story is bound to make you melt (and probably tease him for it forever).
3. If I was a dessert, what would I be? And how quickly would you eat me?
Sweet, flirty, and full of metaphorical mischief. You’re basically asking him to compare you to a treat, which means he has to notice your “flavor.”
Is it molten chocolate cake (dangerous and addictive), or maybe strawberry shortcake (classic but full of surprises)? Either way, it’s a recipe for compliments… and giggles.
4. Would you rather hug me for one hour or kiss me for five minutes?
This one is a no-lose situation. Whether he picks hugs or kisses, the subtext is clear: he enjoys being close to you. It’s soft, intimate, and surprisingly revealing.
Plus, it’s the perfect lead-in to whichever one he chooses.
5. If you had to write a movie about our love, what would the ridiculous plot twist be?
Give his imagination permission to run wild. He might say you’re secretly a time traveler, or that you accidentally adopted a dragon together. The more bizarre, the better.
It’s not just fun. It also gives you both a playful peek into how your relationship feels in storybook form.
6. What’s something totally random I do that you secretly find adorable?
Warning: his answer may make your heart explode. It could be the way you hum in the shower, mispronounce words, or do a little dance while brushing your teeth.
These tiny quirks (the ones you don’t even notice) are often the ones that feel the most personal. And knowing he notices? That’s the real magic.
7. Can you describe our relationship using only emojis?
This one turns into a game real fast. He might go full 💀🔥🧡🧸 or keep it cute with 🐻💋🌮✨.
Whatever combo he sends, you’ll probably end up screen-capturing it for later. It’s a perfect modern love language and lowkey reveals how he views your connection.
8. Would you let me draw a mustache on you while you sleep… for science?
Silly and sneaky just like a good relationship should be. This one walks the line between playfulness and prank potential.
Whether he laughs, groans, or threatens revenge, you’ve already won. Bonus points if you actually test it with a washable marker someday (with consent, of course).
9. What’s your silly pet name for me that you’ll never say in public?
Everyone has that one ridiculous nickname the one that would ruin their street cred if it ever leaked.
Getting him to share it? That’s like unlocking a secret level of your relationship. It’s not just cute, it’s exclusive. Something only the two of you share.
10. How jealous would you be if another dog liked me more than you?
Jealousy with a puppy twist is the best kind of teasing. This question is lighthearted but still flattering: it suggests that even dogs can’t resist you.
The answer will probably include mock horror, dramatic gasps, and maybe a cuddle attack to reassert his place as #1.