70 Playful Texts That Start Flirty Conversations (And Keep Them Going)

Want to flirt without feeling awkward or sounding like every other “hey you” text?
These playful texts are fun, cheeky, and perfect for sparking flirty conversations that don’t fizzle out after two replies.

Whether you’re just starting to talk or keeping things spicy with your crush or boyfriend, these flirty conversation starters are built to tease, charm, and keep the vibes going strong.
From clever openers to saucy one-liners, this list is full of messages that make him smile—and flirt right back.

Fun and Flirty Texts to Start the Conversation

1. Are you always this charming, or is it just when you talk to me?
2. Tell me the first thing that came to your mind when you saw my name pop up.
3. I dare you to say something that’ll make me blush.
4. I feel like causing some mischief—care to join me?
5. If I said I had a flirty question, would you be brave enough to answer?
6. Let’s play a game. I ask, you answer… no holding back.
7. I was thinking about you earlier. Should I feel guilty or flattered?
8. You seem like someone who’s fun to get in trouble with.
9. Are you this good at texting everyone, or am I just lucky?
10. What would we be doing right now if we were in the same room?

Cheeky One-Liners That Keep the Energy Up

11. I should be sleeping, but here I am thinking about your smile.
12. You talk smooth, but I want to know if you flirt better in person.
13. I’ve been good all day—ready to ruin that?
14. I like you. More than I should admit via text.
15. You + me + zero distractions = very interesting conversation.
16. I bet I could make you blush with one question.
17. I didn’t plan to flirt today, but you’re making it very hard not to.
18. You say the word, and I’ll start the chaos.
19. I have a feeling you’re trouble… the fun kind.
20. What’s your favorite way to be teased?

Playful Questions That Keep the Flirting Going

21. What’s your biggest weakness when someone flirts with you?
22. How would you describe your flirting style—in three emojis?
23. What’s something totally innocent that turns you on?
24. Tell me a random fact that’ll make me like you more.
25. If I was right next to you, what would we be doing?
26. What’s your most harmless fantasy? Asking for research.
27. If I dared you to say something bold, would you chicken out or impress me?
28. What do you usually do when someone makes you nervous in a good way?
29. Would you rather kiss slowly or talk dirty until we can’t focus?
30. What’s something you wish I’d ask right now?

Texts That Tease (Without Going Too Far)

31. You popped into my head… and now you won’t leave.
32. If I was with you, I’d definitely be sitting a little too close right now.
33. Guess who almost sent a flirty photo but decided to tease instead?
34. My favorite distraction just texted me. Lucky me.
35. If I told you what I was thinking, we’d both be in trouble.
36. I like where this convo’s going… don’t ruin it by behaving.
37. Do you always have this effect on people, or am I just weak?
38. What are you doing later? And can I be part of it?
39. I may or may not be smiling way too hard at your texts.
40. You’re flirting like you want me to call you later. Should I?

Flirty Compliments That Keep Things Light and Fun

41. You’re dangerously good at this whole flirting thing.
42. You have a way of making boring days feel… not so boring.
43. I wasn’t planning to have a crush this week, but here we are.
44. You’re making it very hard to focus on anything else.
45. I like you more than I probably should.
46. Your texts have no business being this cute.
47. If you’re trying to win me over, it’s definitely working.
48. You might be the reason I’m smiling like an idiot right now.
49. You talk like someone who knows exactly what they’re doing.
50. Honestly, I’m impressed. You keep making this more fun than I expected.

Bold Moves When You Want to Escalate the Flirt

51. Say something bold. I promise I’ll match the energy.
52. Let’s pretend we’re not just flirting. What happens next?
53. I bet I could make you nervous with one well-placed word.
54. If I told you I’ve been thinking about your lips… too much?
55. What would you do if I whispered something naughty right now?
56. I want to say something bold, but I’m deciding if you can handle it.
57. You keep teasing me. Should I tease back or take the lead?
58. I have an idea… it involves you, me, and zero clothing. Too soon?
59. The way you flirt makes me want to get a little reckless.
60. You’re making it very tempting to cross the line—on purpose.

Light-Hearted Texts That Still Keep the Flirt Going

61. I dare you to make me laugh and blush in the same message.
62. Let’s keep this up until one of us gets shy (spoiler: not me).
63. I vote we skip the small talk and flirt shamelessly instead.
64. Texting you is like dessert… totally addictive.
65. I feel like I should be working, but this is more fun.
66. I’d say I’m behaving today… but I’d be lying.
67. What’s your favorite kind of trouble to get into?
68. You’re lucky you’re cute, or I’d pretend to ignore you.
69. You’re quickly becoming my favorite person to flirt with.
70. If this is just texting, I can’t wait to see what real-life flirting looks like with you.

Whether you’re just starting to talk or looking to turn up the spark, these playful texts are perfect for starting flirty conversations that actually go somewhere.
They’re cheeky, confident, and fun—just like the energy you’re bringing to the chat.

So go ahead. Pick one, hit send, and let the flirting begin.