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You love him—but let’s be real: sometimes, you just want to see him laugh like a little kid again.
Not everything in a relationship has to be serious or deep.
Sometimes, it’s the silly, flirty, totally random questions that create the best memories.
Here are 21 romantic questions to ask your boyfriend to make him laugh, open up, and fall for you all over again.
1–5: Playfully Flirty Questions
These are perfect when you’re lying in bed, texting late at night, or sharing dessert on a cozy night in.
- “What was your first impression of me—and how wrong were you?”
- “If you had to give me a nickname based on my worst habit, what would it be?”
- “What’s one thing I do that secretly turns you on, but you’d never admit it?”
- “If we were stuck on a deserted island, which one of us would go crazy first?”
- “Would you rather kiss me in public every day or give up kissing for a month?”
These questions spark laughter, affection, and just the right amount of teasing.
If you want more tips on how to be flirty with a guy over text, read this article next.
6–10: Silly ‘What If’ Questions
Play the what-if game—it’s where goofy hypotheticals and laughter meet.
- “If you could hear my thoughts for a day, what would you expect to hear?”
- “Would you rather forget how to flirt… or accidentally flirt with everyone but me?”
- “If we swapped bodies for 24 hours, what’s the first thing you’d do?”
- “Which cartoon couple are we most like—and why?”
- “If we had a movie about our relationship, what would the title be?”
You’ll learn how he sees you—and how wild his imagination really is.
11–15: Funny Memory Triggers
Bring up the past in the funniest, cringiest way possible.
- “What’s the weirdest date you’ve ever been on (before me)?”
- “Do you remember the first time you tried to impress me—and totally failed?”
- “Have you ever stalked my old social media pics and found something embarrassing?”
- “Which one of us would win in a dance battle?”
- “Tell me the most ridiculous lie you believed as a kid.”
Sometimes it’s not about asking the right questions. It’s about triggering a laugh you’ll both remember.
16–21: Romantic but Goofy
These questions mix affection with just the right dose of dorky.
- “What’s your favorite thing I do when I think no one’s watching?”
- “Would you rather spend a weekend cuddling or on a crazy adventure?”
- “If I cooked a fancy dinner and totally ruined it, would you still pretend it’s good?”
- “What song do you think plays in your head when you see me?”
- “If you could relive one of our dates, which one would it be and why?”
- Bonus: “What would you do if I suddenly challenged you to a pillow fight right now?”
They’re playful. Unexpected. And sweet in the way that only inside jokes can be.
💬 Want to Make Him Even More Obsessed With You?
You already make him laugh—now learn how to trigger the emotions that make him fall deeply in love (and stay there).
There’s one simple phrase that can unlock a whole new level of attraction.
👉 Watch this video to unlock a secret trigger hidden deeply in his mind
These Romanic Questions Will (Hopefully) Make Him Laugh
Laughter builds love. It lowers stress, breaks down walls, and brings you closer in ways you don’t even notice at first.
These questions aren’t just for fun—they’re for connection.
So ask them. Laugh loud. And make new memories that last.
If you want more tips, here’s how to create an emotional connection with him.
Dating Coach Rickard Österholm
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About the author
Rickard is our dating expert here at Chi Rho Dating since 2013, a vlogger with his own show on Youtube, and a podcaster. Rickard has been featured on DatingNews.Com, and GoodMenProject.Com.