Want to know if your crush is into you? These 21 fun questions to ask your crush spark flirty, honest conversations—no awkward vibes, just good energy.
Aren’t just about flirting—they’re your secret weapon to uncover whether the vibe is mutual or just friendly. When you ask the right questions, you skip awkward small talk and get straight into the kind of connection that feels easy, playful, and real.
These 21 questions are low-pressure, high-impact, and perfect for texting, late-night convos, or casual hangs. Let’s dive in.
Why asking fun questions works
When you ask open-ended, unexpected questions, you:
- See how they think (and feel)
- Gauge their sense of humour
- Spot signs of interest, compatibility, or red flags
And let’s be honest—“wyd?” just isn’t cutting it in 2025.
21 fun questions to ask your crush
- If you could instantly master any skill, what would it be?
- What’s your go-to song when you need a confidence boost?
- What's something people always get wrong about you?
- Would you rather have unlimited time or unlimited money?
- What’s your weirdest food combo that actually slaps?
- Have you ever had a crush on a fictional character? Who?
- If your love life was a movie, what genre would it be?
- What’s the most spontaneous thing you’ve ever done?
- What’s one thing on your bucket list you haven’t told anyone?
- Would you rather go on a road trip or a surprise getaway?
- Do you believe in love at first sight—or is that just movie stuff?
- What’s your biggest ick in a relationship?
- When was the last time you had butterflies?
- If we swapped phones for 30 seconds, what would I find?
- What emoji do you secretly overuse?
- Would you rather be famous or totally anonymous (but rich)?
- What’s one thing you wish more people understood about dating you?
- What’s your lowkey flex no one gives you credit for?
- Have you ever sent a risky text and immediately regretted it?
- What’s the most “you” thing you’ve ever done on a date?
- If we got stranded on a desert island, what’s the one thing you’d bring?
How to ask these questions (without being cringe)
- Use humour. “Okay, serious question: what’s your toxic trait when it comes to pizza toppings?”
- Drop them casually in conversation or over text
- Use the “you first, then me” format to build comfort
Make it feel like a game, not an interview. If they’re into you, they’ll match your energy—or go deeper.
Signs they’re into you (based on their answers)
- They ask you the same questions back
- They get playful or flirt when answering
- They open up instead of keeping things surface-level
- They drop personal details without being asked
If the vibe feels mutual, don’t overthink it. Keep the questions rolling and see where it leads.
Want help reading deeper signals?
Don’t forget: Tone matters more than the words
Confidence > perfection. The way you ask is more important than what you ask.
- Be light, be curious, be respectful
- Don’t force it if they’re not giving the same energy
- If they’re dry, maybe that’s your answer
Real interest looks like engagement—not just replying.
What the experts say about playful connection
- Playful banter increases romantic interest by 62% (Psych Today, 2024)
- Questions that evoke personal memories create stronger bonds (Journal of Social Psychology)
- Flirty Q&A reduces first-date awkwardness by 40% (Match.com survey)
Other fun guides from IChhori
Fun questions to ask your crush can open the door to real connection. You don’t need cheesy pickup lines—just a little curiosity, confidence, and good timing. Ask the right question, and the answer might just surprise you—in the best way.