Juicy, Deep & Flirty: Questions to Ask Your Boyfriend

Let’s be real—text convos can get dry, especially when “wyd” and “nm” are all you’re working with. But asking the right questions? Game-changer. Whether you’re just starting to vibe or years into your relationship, knowing what to ask your boyfriend can build chemistry, spark laughter, and reveal his deeper side.

Think of this as your personal question playbook. From blush-worthy to bold, here’s how to turn chats into heart-racing, giggle-filled, soul-touching convos.

What Interesting Questions Can I Ask My Boyfriend?

Skip the boring “how was your day?” and dive into things that actually bring you closer. Ask him stuff that makes him pause, think, and smile.

Try “What’s one memory from childhood that still makes you laugh?” or “If we could disappear for a weekend, where would you take me?” Questions like these spark emotion, not yawns.

You can even get a little weird with it—“Would you survive a zombie apocalypse?” You’ll learn more than you think.

What Are 21 Questions to Ask Your Boyfriend?

Need a solid list to keep convos rolling? Here’s your 21-question cheat sheet for fun, romance, and maybe a few revelations:

1. What was your first impression of me?
2. If you could relive one day, what would it be?
3. What’s one thing you’ve never told anyone?
4. What’s your weirdest turn-on?
5. Would you rather kiss me in the rain or under the stars?
6. If we had a theme song, what would it be?
7. How old were you when you had your first crush?
8. What’s your ultimate bucket list item?
9. Have you ever had your heart broken?
10. What’s your favorite part of my body?
11. What’s the most spontaneous thing you’ve ever done?
12. If we had a time machine, where would we go?
13. Do you believe in fate?
14. What would your dream date night look like?
15. What’s one thing you’re dying to try in bed?
16. Who’s your celeb crush?
17. Do you think love at first sight is real?
18. What song makes you think of me?
19. What do you want us to be doing in five years?
20. Have you ever written someone a love letter?
21. What do you love most about being with me?

What Questions Make a Boy Blush?

Want to see him go all shy and squirmy in the cutest way? Hit him with compliments that catch him off guard.

Ask, “Do you realize how hot you are when you’re focused?” or “Have you ever imagined what it’s like to wake up next to me every day?”

Tease him with, “When did you know you were in trouble with me?” Cue the blush.

What to Ask a Guy Flirty?

Flirty questions add spice—light teasing, playful vibes, and just enough heat to keep things fun.

Try “If I were a dessert, what would I be?” or “How long could you last without kissing me?” It’s all about tone and timing.

You can even go for, “What would you do if we were alone right now?” That one’s a classic.

What Are Some 18+ Questions?

Let’s not pretend we don’t all have a naughty side. Ask with confidence, and keep it consensual and respectful.

“Ever had a steamy dream about me?” or “What’s your biggest turn-on?” will light things up quickly.

More? “Where’s the craziest place you’ve fantasized about doing it?” That one always hits.

How to Flirt with Guys Over Text?

Flirting over text isn’t just emojis and “heyyy.” It’s about building tension, mystery, and connection.

Send him “If I was there right now, what would you do?” or “Guess what I’m wearing (wrong answers only).” It keeps things playful.

Use voice notes too—your tone can say way more than your words.

Dare to Ask Your Boyfriend?

Dares turn into unforgettable moments. Ask him fun challenges that get him out of his comfort zone (or shirt).

“Send me a voice note saying something sweet in your ‘bedroom voice.’” Or “Dare you to plan our next date—no hints.”

Make it spicy or silly—it’s the surprise that’s fun.

How to Tease Your Boyfriend Over Chat?

Text teasing is an art. Drop a subtle flirty bomb, then leave him hanging—make him work a little.

Say “I just had the most interesting thought about you… but I’ll tell you later.” Or “You’d look so good in nothing but a smirk.”

Keep it cheeky, not cheesy.

Questions to Ask Your Boyfriend to Test His Love

Testing his love doesn’t mean playing games—it’s about seeing how deep he really feels.

Ask, “Would you fight for us if things got tough?” or “What’s one sacrifice you’d make for me without a second thought?”

Or drop this gem: “If we broke up, what would you regret not doing with me?”

Romantic Questions to Ask Your Boyfriend to Make Him Laugh

Laughter and love? Perfect combo. Use questions that are sweet, but also just a little goofy.

Try “Would you still love me if I turned into a potato?” or “How many kisses a day is too many?”

Even “What’s one silly thing about me you secretly adore?” will get a chuckle and aww in one go.

Trick Questions to Ask Your Boyfriend

Want to keep him on his toes? Ask questions that have no easy answer, or double meanings.

“Would you rather date someone hot or someone like me?” See how fast he backpedals.

Or, “If you could only save one thing—me or your phone—what would it be?” The smart ones always say you. Hopefully.

Whether you’re texting, calling, or curled up together, asking the right questions can turn any moment into magic. It’s not about interrogating him—it’s about discovering the layers of the person you love (and making him blush while you’re at it).

So the next time your convo feels stale or you’re just in the mood to play, pull out one of these and watch the sparks fly.