Talking to your crush can feel like a mix of fun and nerves.
You want to come across as natural, but sometimes your mind goes blank when you finally get in front of them.
One thing I’ve learned with coaching clients is the more we like someone, the weirder we tend to act.
That’s why asking a good question can take all the pressure off and make the moment feel much easier. This is why I pulled together some of the best questions to ask your crush.
These questions will give you both food for thought, help keep the conversation flowing and make it feel easier.
Playful & Funny Questions to Ask Your Crush
Starting with something light makes it easier for both of you to relax.
A little humor goes a long way when you’re just getting to know each other.
- What’s the funniest way you’ve ever been injured?
- What’s the worst pickup line you’ve ever heard (or said)?
- If animals could talk, which would be the rudest?
- If your life were a movie, what songs would be on the soundtrack?
- What’s the most embarrassing thing you’ve ever worn?
- What’s your guilty pleasure TV show or movie?
- What’s the silliest thing you’ve ever done?
- What always makes you laugh no matter what?
- What’s your most ridiculous fear?
- If you could be any fictional character, who would you be?
Casual & Easy Conversation Starter Questions to Ask Your Crush
The easy questions are often the ones that get the most honest answers.
These give you a natural way to learn what they enjoy without it feeling forced.
- What’s your favorite way to spend a Friday night?
- What kind of music instantly puts you in a good mood?
- Which movie could you watch on repeat without getting tired?
- What’s your signature dish in the kitchen?
- What’s your favorite dessert when you want to celebrate?
- If you could relive one amazing day, which would it be?
MORE: 101 Thought-Provoking Questions To Get To Know Someone
Cute and Flirty Questions to Ask Your Crush
These are lighthearted ways to see if the attraction is mutual. Just enough to see if the spark is there.
- Do you think you’d win in a game of truth or dare?
- When was the last time someone made you blush?
- What’s one little thing that always gets your attention?
- Would you rather have breakfast in bed or a sunset picnic?
- Which season do you think is the most romantic?
- Which holiday would you celebrate all year if you could?
- What’s your favorite lazy-day activity?
Romantic Questions to Ask Your Crush That Build Chemistry
Once you feel more comfortable, you can ask things that lean a little closer to romance.
These questions to ask your crush are good for finding out if the interest runs deeper.
- If we were sharing a bottle of wine right now, where would the night go next?
- Have you ever had a moment with someone where the air felt electric?
- What’s your idea of a perfect morning?
- What’s the most memorable kiss you’ve ever had and why?
- If you could steal someone away for a weekend, what would you plan?
- If we danced close, would you whisper something in my ear or keep it to yourself?
- What’s the best kind of trouble two people can get into together?
- If we were the only ones in the room, how would you keep my attention?
What-If Scenarios to Ask Your Crush
What-if questions are fun questions to ask your crush, but they also show you how someone thinks and imagines.
They can often reveal more than you might expect.
- Do you believe in love at first sight, or should it take more than one date?
- Which do you enjoy more: a slow dance or a fast one?
- If someone wanted to sweep you off your feet, how should they do it?
- Do you think you’re more of a heartbreaker or a heart-stealer?
- What’s your favorite compliment to receive?
- If you won the lottery tomorrow, what’s the first fun thing you’d buy?
- If you could only eat one dessert forever, which would you choose?
- If you could time travel to any year, where would you go first?
- If you had to plan a date with just $20, what would we do?
- What’s your go-to song to dance to when no one’s watching?
- What’s one adventure you’ve always wanted to go on?
- Have you ever had a date you didn’t want to end?
- If you could instantly master one hobby, what would it be?
The best part about asking your crush the right questions is how it takes the pressure off you.
Instead of scrambling for what to say next, you can enjoy the back and forth and actually get to know them.
Pick a few of these questions and keep them in mind.
Sometimes one simple question is all it takes to turn small talk into something memorable.
The truth is, connection doesn’t come from saying the perfect thing. It comes from being curious and present.
MORE: 53 Flirty Questions to Ask When You’re Sick of Small Talk
