50 Flirty Questions to Make Him Smile Through the Screen

The experiences shared in this article are based on real emotional journeys, but all personal details are anonymized and used with the explicit written permission of the clients. Any resemblance to actual persons, living or dead, is purely coincidental. We are committed to treating all client stories with the utmost confidentiality and respect.

When you’re texting someone you’re into, and things feel just a little… electric, it’s easy to get stuck between wanting to be playful — and overthinking every typed word like it’s a job interview answer. Should you be cute? Clever? Casual? Is “😏” too much? Will “lol” sound passive-aggressive?

I’ve been there. So have the hundreds of women I’ve coached — women who want to flirt, yes, but do it in a way that feels true to who they are: emotionally intelligent, not gimmicky. Soft, not submissive. Powerful, but not performative.

So how can you be flirty in a way that makes him lean in instead of checking out? How do you make him smile at his screen at 11:42pm and think, “Damn. She’s different.”

You ask the kind of questions that make him laugh, think, feel, and — subtly, maybe even hungrily — want to know more.

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Let’s get into it.

Here are 50 flirty questions designed for texting, FaceTiming, or messaging — set up to create chemistry, draw him closer, and still leave space for you to leave a little to the imagination.

They’re divided into five intentions, depending on where you are in the conversation — and your connection.

Because not all flirting looks the same. But the best kinds? They feel like home with a spark.

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Save this article for later—Pin it to Pinterest and come back when you need it! 📌

Section 1: I Just Met You… But I’d Totally Steal Your Hoodie

(aka Funny + Charming Ice-Breakers)

These are for those early days — maybe post-match, or after exchanging numbers. You want to hint at interest, show you’re paying attention, and set the tone that something here could be… fun.

1. Be honest — did you actually read my profile or were you just hypnotized by my face?
2. What’s your “I probably look hot doing this” everyday activity?
3. 3am conversation or 8am coffee date — which one’s more dangerous with me?
4. If we were on a reality dating show, how long before we’d fake a scandal just to get more camera time?
5. What’s your love language… and what’s your most chaotic flirting tactic?
6. What’s something you’d only ever tell someone you’re trying to impress? (I’m listening.)
7. You send me a playlist that reveals your personality. Should I fall in love now or later?
8. What’s your ideal “accidentally romantic” situation with a stranger?
9. If I suddenly showed up at your door in my pajamas, snacks in hand… what movie are we watching?
10. When’s the last time someone completely surprised you (in a good way)?

Try asking one of these when the energy starts to fade after “So how’s your day been?” Being funny is flirty. Being curious is sexy. (And being yourself is undefeated.)

💫 Little reflection: Which one of these made you want to text someone immediately?

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Section 2: Let’s Be Honest… We’re Both Kinda Into Each Other

(aka Confidence in a Soft, Sizzling Form)

At this point, you’re vibing. Maybe your texts go till late. Maybe you’re planning that third FaceTime. These questions lean into that new intimacy — the “I want to know more about how you work… and maybe how I could drive you a little wild.”

11. When you’re really into someone, what gives it away — even if you’re trying to play it cool?
12. What’s something innocently sexy a person can do that completely captures your attention?
13. I dare you to describe your type without using the word “hot.”
14. What’s your favorite kind of tension — the kind that makes you nervous or the kind that makes you stay?
15. When do you feel most irresistible — intentional or accidental?
16. What’s something I’d do that would instantly make you jealous (in a flirty way)?
17. What’s a body language signal you always notice on someone you’re into?
18. What’s worse: catching feelings too soon or pretending you haven’t caught them at all?
19. We make eye contact from across a crowded room. Tell me what happens next.
20. Do you like being teased… or doing the teasing?

These questions slowly turn up the dimmer. They’re playful, not pushy, and invite him to bring his attention — and yes, his desire — more fully into focus.

🔥 Tip from a coach (and a woman who’s been on that side of the screen): You don’t have to set the fire. Just be brave enough to strike the match.

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Section 3: Gentle Seduction — With a Side of Soul

(aka Flirty but Thoughtful, Intimate but Chill)

Want to flirt in a way that hits a different octave? Here’s how we start building emotional attraction — the kind that wraps curiosity and connection into something you both want more of.

21. What’s something small someone once did that made you feel seen in a way you didn’t expect?
22. What do you secretly wish someone would notice about you?
23. What’s your private “soft spot” — the thing that turns you into a puddle of affection?
24. How do you like to be flirted with when no one’s watching?
25. Is there a memory you go back to when you’re trying to fall asleep… and would you tell me what it is?
26. When’s the last time you felt genuinely wanted — like, actually?
27. What sounds flirty but feels vulnerable to you?
28. What does intimacy mean to you when no one else is defining it?
29. Is there something about me (so far) you’re curious to explore more?
30. Do you believe there’s a difference between chemistry and compatibility — or have you ever had one without the other?

These are the kinds of questions that feel like slipping into a deeper pool. You don’t dive in headfirst — but you feel the warmth, the depth, the stillness below the surface.

🌿 Little moment of truth: Have you ever asked someone a question that made them slow down before they answered? That’s how you know you’re getting real.

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Section 4: The Hotter Side of Playfulness

(aka Suggestive, Sexy-ish, But Still Thoughtful)

Things are heating up. There’s back-and-forth banter, a late-night FaceTime or two with lingering silences, and you both know…you’re flirting for a reason. These questions let you go there — smartly.

31. What’s one innocent situation that completely turns into flirting for you?
32. What outfit would make you lose focus for an entire date?
33. What’s your secret move when you really want someone to make the first move?
34. What’s sexier: anticipation or surprise?
35. What’s your version of “take me home right now” energy?
36. What’s something subtle you wish more people did… and would melt for if I tried it?
37. Have you ever had one of those “we shouldn’t, but we totally might” kind of moments?
38. You had a long day. I’m at your place. How do I show up for you — flirt version?
39. If I leaned in a little too close, what would you do?
40. What’s your most flirtatious thought all day…. and can you tell me safely?

Is this where things get a little steamy? Maybe. But with intention. Women I coach often worry about setting boundaries and still being desirable. These questions show you can be inviting… without giving more than you’re ready to.

💋 Thought to hold: Flirty doesn’t mean overexposed. Sometimes, the sexiest thing you can do is leave room to imagine.

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Section 5: For When You’re Both Low-Key Already Obsessed

(aka Spicy + Sweet… But Heading Somewhere Real)

You’re talking daily. Maybe you both “pretend” the other’s Instagram stories just showed up on your feed. He’s memorizing your favorite drinks. These questions feel a bit more personal — like you’re daring to define what this might be.

41. What’s the one thing I do (or say) that makes you feel something — even if you try not to show it?
42. If we spent a weekend together — no distractions — what’s happening?
43. What would make you fall, faster than you expected?
44. What’s your idea of foreplay that starts with the mind, not just the body?
45. When do you know you’re actually in trouble… like, falling-for-someone trouble?
46. How long did you wait before you started imagining a “what if” about us?
47. Would you rather give butterflies or feel them?
48. Want to do something a little reckless… like plan a pretend date night we can’t possibly top?
49. How are you when you really, really miss someone?
50. Finish this for me: “If this turns into something… I hope we never stop _____.”

At this level, the flirting doesn’t just make you smile — it makes you want more. More time. More words. More closeness.

🖤 Inner check-in: Did one of these hit too close in the best way? That’s usually a good sign.

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Final Words from The Darling Code

Here’s the truth: To flirt beautifully isn’t to pretend you don’t care. It’s to show that you care — just enough to make someone’s night feel more magnetic, more alive, more full of what-if.

So where do you begin?

Pick 2 or 3 of these questions — not just the ones that sound flirty, but the ones that make YOU feel excited to ask. Drop one into the next conversation. Not all at once. Let it simmer. Then watch how he responds — not just with his words, but how quickly (and how curiously) he answers.

Remember, flirting isn’t performance. It’s connection… wrapped in spark.

With heart,
The Darling Code

P.S. Save this list to your Pinterest so you’re never left saying “so what’s up?” again. Share it with your single BFF. And if you’re texting a certain someone tonight, start with #3 or #23 — they both hint, without pushing. Try one, and see what opens.

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