Starting a flirty conversation with your crush can feel a little scary, but it doesn’t have to be complicated.
The right question can break the ice, spark real chemistry, and turn an ordinary chat into something you’ll both think about later. It’s not about having the perfect line; it’s about being playful, curious, and just a little bit bold.
If you’re ready to make them blush, laugh, and maybe fall for you a little harder, you’ll find plenty of fun ideas right here.
Deep Flirty Questions to Spark Chemistry
1. If you could spend one day anywhere in the world with me, where would we go?
2. What’s one thing you’ve always wanted to do with someone you’re dating but haven’t yet?
3. When you first saw me, what was the first thing you noticed?
4. What’s something completely random that instantly makes you think of me?
5. If we were stuck together on a deserted island, what’s one thing you’d hope I brought with me?
6. How do you usually show someone you’re into them without actually saying it?
7. Be honest—what’s something small I do that you find insanely attractive?
8. If you could steal one moment from a romantic movie and live it with me, which scene would it be?
9. What’s the most unexpected thing you find really cute about me?
10. If you had to pick one word to describe our connection so far, what would it be?
11. What’s your idea of a perfect “just us” kind of night?
12. What song instantly makes you think about love—or about me?
13. If I dared you to kiss me right now, would you do it?
14. What’s something you’ve been dying to ask me but haven’t yet?
15. What’s the most ridiculous thing you’d do just to make me laugh?
16. If we could pause time for a day, what’s the first thing you’d want to do together?
17. What’s your favorite part of getting to know me so far?
18. When you imagine your dream date, what’s the first thing that pops into your head?
19. Do you believe in that “spark” people talk about when two people just click instantly?
20. What’s one little thing I do that you think is way more attractive than I realize?
21. If you could read my mind for 10 minutes, what’s one thing you’d hope to find out?
22. What’s the most flirty thing you’ve ever done without meaning to?
23. If you had to pick: long conversations late at night or stolen glances across a crowded room?
24. Have you ever caught yourself smiling at your phone because of me?
25. If we were slow dancing right now, what song would you want playing?
26. What’s one thing you secretly wish I’d do when we’re together?
27. If we spent a weekend away, would you want crazy adventures or lazy mornings in bed?
28. What’s the one place you’ve always wanted to kiss someone but never have?
29. What’s something you think would instantly make us even closer?
30. If you had to describe me using only emojis, which ones would you pick?
Playful Flirty Questions to Make Them Blush
31. Be honest—how long did you stalk my Instagram before you texted me?
32. If you had to give me a nickname based on our first impression, what would it be?
33. What’s the most trouble you think we could get into if we spent an entire day together?
34. Would you rather win a million dollars or spend 24 hours alone with me doing whatever you want?
35. What would you do if I randomly showed up at your door right now with pizza and no plans?
36. On a scale from 1 to “head over heels,” how much do you enjoy talking to me?
37. Have you ever lied about being busy just so you could keep texting me?
38. Would you rather steal my hoodie or my heart first?
39. If we had a secret handshake, what ridiculously silly thing would you add to it?
40. What’s more fun: late-night drives with loud music or staying in and building a fort out of blankets?
41. Would you let me win a game just to see me smile, or would you crush me and make me work for it?
42. What’s your go-to move when you’re trying to flirt but pretend you’re not?
43. Which would you rather do: a spontaneous road trip with me or a cozy movie marathon?
44. If I dared you to plan a surprise date for us, how wild would it get?
45. How long did it take you to realize you had a little crush on me?
46. Would you rather kiss me under the stars or during a rainstorm?
47. What’s something totally innocent that would absolutely give you butterflies if I did it?
48. What’s your fake excuse going to be when you text me later just because you miss me?
49. Who do you think would win in a tickle fight—you or me?
50. If you had one cheesy pickup line to use on me right now, what would it be?
51. What’s your secret move to get someone’s attention when you’re crushing hard?
52. Would you rather have a lifetime supply of pizza or a lifetime of hugs from me?
53. If we had a code word to escape boring events together, what would it be?
54. What’s one ridiculously cute thing you’d love for us to do together but haven’t admitted yet?
55. Would you ever dare me to kiss you in public just to mess with people?
56. Which would you pick: slow dancing in a random parking lot or a midnight swim at the beach?
57. How long could you go without texting me before you gave in?
58. What’s the first thing you’d want to do if we got snowed in together for a weekend?
59. If I challenged you to a flirty staring contest, who do you think would win?
60. What’s one thing you’ve imagined us doing together that you haven’t said out loud yet?
Cheeky Questions to Build Romantic Tension
61. If I leaned in really close right now, would you pull me closer or tease me by backing away?
62. What’s more tempting to you right now: a slice of your favorite dessert or stealing a kiss from me?
63. Be honest—if we were sitting next to each other right now, how hard would it be not to touch me?
64. If I whispered something sweet in your ear, would you smile or blush first?
65. What’s the one move you know would absolutely drive me crazy if you did it?
66. If I told you I can tell when you’re checking me out, would you deny it or just smirk?
67. What’s more dangerous: your smile or your eyes? Because honestly, I’m struggling here.
68. If I dared you to kiss me somewhere unexpected, where would you pick?
69. If we were slow dancing right now, would you pull me closer just because you could?
70. What’s the first thing you notice about me when I walk into a room? (And yes, you have to tell the truth.)
71. If you could magically teleport me to you right now, what would we be doing?
72. What’s something innocent I could do that would totally mess with your focus?
73. If I gave you three seconds to grab my hand or my waist, which one are you choosing?
74. Would you rather catch me staring at you or catch me biting my lip thinking about you?
75. What’s one thing you secretly wish I would dare you to do when we hang out next?
76. How many times have you almost texted me something flirty but chickened out at the last second?
77. If you could only kiss me once today, would you do it slow and sweet—or fast and leave me wanting more?
78. If I called you right now and told you to come over, how long would it take you to get here?
79. What’s one thing you think would instantly break the tension if we got too close?
80. If you were trying to get my attention without saying a word, what would you do?
Flirty “Would You Rather” Questions to Tease Your Crush
81. Would you rather spend an entire day cuddling or sneaking kisses in random places?
82. Would you rather get caught staring at me or get caught texting me something flirty?
83. Would you rather have me send you a cute selfie or surprise you in person?
84. Would you rather dance with me in the rain or build a pillow fort and watch movies all night?
85. Would you rather share a super slow first kiss or an unexpected, laughing kind of kiss?
86. Would you rather tease me until I give in or let me completely wreck your concentration?
87. Would you rather me call you cute all the time or give you a flirty nickname no one else knows?
88. Would you rather steal my hoodie or my attention for a whole day?
89. Would you rather have me flirt with you all day through texts or whisper flirty things in your ear when we’re together?
90. Would you rather lock eyes across a crowded room or sit so close our knees touch?
91. Would you rather me catch you daydreaming about me or catch you writing my name somewhere?
92. Would you rather go on a spontaneous road trip with me or get lost wandering a city together?
93. Would you rather me mess up your hair by playing with it or make you forget your words just by smiling at you?
94. Would you rather kiss under fireworks or under fairy lights?
95. Would you rather me compliment your looks or your laugh?
96. Would you rather have a flirty conversation that leaves you blushing or a silent moment that says everything?
97. Would you rather tease me until I blush or get me to laugh so hard I can’t breathe?
98. Would you rather share a secret with me or have me figure it out just by looking at you?
99. Would you rather hold my hand during a scary movie or let me hide my face in your shoulder?
100. Would you rather have me dare you to kiss me—or dare you to make me fall harder for you?
