100 Really Good, Flirty Questions to Ask Your Crush & Make Them Think of You
The flirtiest questions to ask your crush to break the ice, build sexual tension, and secretly find out if they like you too. Use these with charm.
Looking for good, flirty questions to ask your crush might seem silly, but they work for a reason, they build curiosity, connection, and playful sexual tension. That’s not just vibes talking; it’s psychology.
Research shows that reciprocal self-disclosure, especially in the form of questions, increases attraction and emotional closeness faster than ordinary conversation.
📚 Source: The Experimental Generation of Interpersonal Closeness, Aron et al., 1997
So when you ask your crush flirty questions, especially the kind that make them blush, laugh, or flirt back, you’re not just making small talk. You’re creating chemistry.
The only problem? Most people freeze up and have no idea what to say in the moment. So here’s your cheat sheet: a list of flirty questions that’ll make your crush smile, wonder what you’re thinking, and maybe even start thinking about you in a whole new way.
Pick your favorites, use them playfully, and see what they reveal!
[Read: How to flirt with a friend – 18 ways to tease them without being weird]
How to relax when flirting
Flirting should be natural and romantic, right? Well, sure, if you are a character in a movie. But, in real life, nerves, social anxiety, and awkwardness come into play.
All of these make flirting with your crush feel scary. But, it doesn’t have to be. You can be relaxed when flirting.
To start, one way to been less nervous is to flirt over text. This gives you some leeway. You have time to think before responding and won’t have that fear of making a fool of yourself.
If you only see your crush in person, being prepared can help you feel less on edge. By having some topics and flirty questions to ask your crush in the back of your head, you feel ready to chat.
Lastly, be open. Try not to build things up in your head too much. You don’t need to come out of every conversation knowing that your crush likes you back. Sometimes, the fun of flirting is the unknown. [Read: Learn how to be relaxed on a date]
Have confidence
Flirting is all about confidence. Rather than second-guessing yourself, feel proud of yourself.
Instead of being scared of rejection or anticipating the worst, be open to flirting for a while or having a quick back and forth. Maybe this will work out. Perhaps you’ll just be friends.
But, if you can go in with confidence, you can start the conversation, and let it flow. Try not to focus on what to say next. Instead, listen to what they’re saying and follow up.
Be present in the moment and the confidence will find you. [Read: 16 ways to build self confidence and realize you’re worth it]
Flirty questions to ask your crush
When flirting, the best questions to ask your newly found crush are ones that help you get to know them and draw attention to their personal life.
Furthermore, these questions will plant the idea that you’re interested and help you find out more about them, their interests, and their personal tastes.
With this in mind, you should pick and choose the ones that best fit your interests and theirs. For fear of seeming too rehearsed, you don’t need a script or to memorize your favorites.
Instead, make them your own and ask them with confidence. [Read: The quickest ways to know if your crush isn’t into you]
1. Have you been working out?
2. What are you looking for in a girl/guy?
3. How can someone like you not have a boyfriend/girlfriend?
4. How did you get so attractive?
5. How are you so good at _______?
6. What would be your ideal date?
7. Why are you so funny? [Read: 40 unbelievably cute things you can say to your crush]
8. What did you first think of me?
9. What’s the most romantic date you’ve ever been on?
10. Who’s your celebrity crush?
11. Do you like girls/guys who make the first move?
12. Would you rather be considered sexy or smart?
13. Are you looking to get a boyfriend/girlfriend anytime soon? [Read: 6 subtle questions you can ask your crush to know if they like you back]
14. What’s the one thing that makes you the happiest?
15. Where do you feel the most relaxed?
16. Are you more of a beach or a lake person?
17. How would you react if I told you how attracted I am to you?
18. What are your favorite pet names?
19. What’s your biggest turn on when dating someone?
20. How would you describe yourself in 3 words?
21. Okay, now how would you describe me in 3 words?
22. What is the most attractive physical feature on someone you’ve considering dating? [Read: 36 racy, random questions for flirty guys and girls]
23. What’s your type?
24. Do you have any tattoos?
25. Have you ever been skinny dipping?
26. *If answer to previous question is “no”* Would you ever go skinny dipping? 😉
27. Are your parents as good-looking as you?
28. What’s the most embarrassing thing that’s ever happened to you when you were with a significant other?
29. Would you prefer to make out or cuddle? Or make out, then cuddle? 😉
30. If you could have any job in the world, what would it be? [Read: 20 revealing questions to get to know someone a lot better]
31. Do you prefer a pool or a hot tub?
32. Have you ever had sex on the beach? No. I don’t mean the drink.
33. What’s one thing it’s okay to lie to your partner about?
34. What’s the best pick-up line you’ve ever heard?
35. What was your very first date like?
36. What makes you the most nervous? [Read: 50 questions to check if someone’s right for you]
37. Would you rather be invisible or have x-ray vision? 😉
38. If you could change one thing about your life right now, what would it be?
39. What is the weirdest place you’ve hooked up with someone?
40. Your smile is amazing. Did you have braces or were you just blessed with amazing genes?
41. Do you like being the little spoon or the big spoon?
42. What is the most romantic food?
43. Who is your favorite celebrity couple? [Read: Love advice from famous couples]
44. Who do you admire the most in your life?
45. What do you want to know about me?
46. What is the most romantic movie scene?
47. Are you more of an introvert or an extrovert?
48. Do you think you have a good judge of character?
49. What is the best emoji to use when flirting? [Read: 17 cute, flirty and naughty emojis people use when they like you]
50. What is the most romantic thing you’ve ever done for someone?
51. What are you the most confident about?
52. What do you judge other people for?
53. Do you prefer to stay in or go out?
54. What are you most passionate about?
55. What do you love most about traveling?
56. What is the best part of dating someone new? [Read: 50 really cute things to say to your crush and make them feel special]
57. If you could change one thing about modern dating culture, what would it be?
58. Are you stubborn or open?
59. Are you ticklish?
60. What makes you nervous? [Read: How to calm the voice in your head]
61. Do you like massages?
62. What is something you want to learn more about?
63. Are you sentimental?
64. Do you believe in love at first sight?
65. What is your biggest turn-off?
66. Do you prefer texting or talking on the phone?
67. Do you like sharing a bed?
68. What has failure taught you? [Read: How to come back from failure]
69. What fictional characters do you ship the hardest?
70. What did you like most about school?
71. If you could only have one thing on your bucket list, what would it be?
72. How do you feel about marriage?
73. What do relationships need in order to survive?
74. What would I be surprised to learn about you?
75. How about we go out sometime?
76. What would you do if we were alone in a room with zero distractions?
77. What’s your favorite excuse to text someone you’re crushing on?
[Read: 38 Ways to Start a Conversation Over Text & Make Each Text Fun to Reply]
78. What’s something I do (or say) that you secretly like?
79. What’s your toxic flirt habit?
80. If I sent you a “thinking of you” emoji right now, what would your reply be?
81. Who usually catches feelings first, you or the other person?
82. What do you think my type is?
83. If I dared you to send me your flirtiest selfie, would you do it?
84. What’s your love language, and what’s your flirting language?
85. What’s something you always notice first when you like someone?
86. If I sat really close to you right now, what would happen?
87. Do you think eye contact can make people fall in love?
[Read: 29 Secret Ways to Subtly Flirt & Make Them Desire You Subconsciously]
88. What’s your ideal “accidental sleepover” scenario?
89. Who would play us in the rom-com version of our story?
90. If we had to pretend to be a couple for 24 hours, what would we do?
91. Have you ever had a crush on someone you shouldn’t have?
92. What would your friends say if they knew you were talking to me like this?
93. What’s the biggest sign someone’s flirting with you?
94. How do you secretly flirt when you’re trying to be lowkey?
95. What’s one thing you wish someone would text you at 2 a.m.?
96. Would you rather send a flirty voice note or a flirty pic?
97. If I kissed you right now, what would you do?
98. When’s the last time someone gave you butterflies?
99. Would you ever go on a spontaneous weekend trip with your crush?
100. What’s your biggest turn-on that most people don’t know about?
[Read: The right way to talk to your crush and make them fall hard for you]
How to use these flirty questions (without being weird)
Flirty questions are meant to open doors, not kick them down. The key is to keep the energy playful, like you’re suggesting something cheeky, not cornering them into anything intense. Think of these questions like conversational foreplay: you’re sparking curiosity, not demanding answers.
According to the Interpersonal Deception Theory (Buller & Burgoon, 1996), people are more likely to feel at ease and engage authentically when they perceive a low-threat, relaxed environment. That means your tone matters more than the words themselves.
📚 Source: Interpersonal Deception Theory – Buller & Burgoon, 1996
So before asking something bold, warm things up with eye contact, a smile, or even your own answer first. For example: “Would you rather make out or cuddle?” becomes a lot more fun when you follow it with, “Personally, I’m all about the make out, then cuddle combo.”
The best part? If they flirt back, you’ve got momentum. If they pull back, that tells you something too. Either way, you’re steering the vibe without forcing it, and that’s the real flirting sweet spot.
👉 Looking for more flirty questions? Try these!
- 115 Freaky, Sexual Questions to Ask Friends & Have a Dirty, Naughty Time
- 60 Deep, Fun Questions to Get to Know Someone Romantically as a Match
- 83 Dating Questions to Ask in the Talking Stage to Get to Know Them Deeper
- 40 Very Deep Questions To Ask Someone Before You Get Close to Them
- 72 First Date Questions, Conversation Starters & Things You Should Never Ask
When’s the right time to ask these questions?
Timing is everything when it comes to flirty questions. Drop them too soon and it can feel forced. Wait too long and the moment passes. The sweet spot? Right after you’ve exchanged a few laughs, shared a personal moment, or felt a little spark, online or in real life.
Research into Uncertainty Reduction Theory (Berger & Calabrese, 1975) shows that when people are first getting to know each other, they naturally seek to reduce uncertainty, and asking questions is one of the key ways we do that. Flirty questions, specifically, reduce emotional distance while keeping things fun.
📚 Source: Uncertainty Reduction Theory – Berger & Calabrese, 1975
Texting late at night? Perfect time. Hanging out and laughing over drinks? Ideal. On a walk or sitting next to each other on the couch, casually scrolling? Chef’s kiss.
And if the conversation feels dry or stuck in “what do you do for fun?” territory, that’s your cue to spice things up. You’re not trying to trap them in a flirty Q&A, you’re creating a moment, a vibe, a spark. Let the questions be playful nudges toward something that feels exciting, mutual, and real.
[Read: 250 Fun, Deep Relationship Questions for Couples to Feel Closer & More Loved]
These flirty questions to ask your crush aren’t just for laughs, they’re connection catalysts. Whether you’re texting late at night or flirting face-to-face, go ahead. Ask the question. See what happens. Sometimes all it takes is a spark.
