Starting a flirty conversation over text shouldn’t feel like defusing a bomb. But sometimes, knowing what to say without sounding awkward or obvious? Not so easy.
I’ve sent my fair share of texts that were either too boring or too bold. Some got ignored. Others kicked off days of fun back-and-forths. And the difference always came down to one thing: playfulness.
The kind that makes him grin at his phone.
If you’re trying to get the spark going (or keep it alive), these flirty texts are the perfect way to nudge the door open—with just enough sass, charm, and curiosity to keep him replying.
Let’s get those conversations buzzing.
Light and Easy Starters
Perfect when you’re just starting to vibe
These openers are casual, fun, and low-pressure. Think of them as a flirty tap on the shoulder—just enough to get noticed, without giving too much away.
- “So, do you always look this good, or is today special?”
- “Tell me something that’ll make me smile. No pressure.”
- “I was going to wait to text, but here I am being impatient.”
- “On a scale from 1 to ‘I’m blushing’—how good is your flirting today?”
- “I had a dream about you. Should I be concerned?”
- “You popped into my head. So now I’m popping into your texts.”
- “Guess what I’m thinking right now. Hint: it’s a little bit about you.”
- “You’re trouble, huh? I can tell.”
- “Is it weird that texting you is my favorite hobby now?”
- “If I start this convo, you better keep it going.”
Cute Questions That Get Him Talking
Playful prompts he can’t resist answering
These texts are a clever way to start the flirty dance while also letting him do a bit of the work. And let’s be honest—guys love a good opening.
- “What’s your go-to move when you’re trying to impress someone?”
- “What’s the worst pickup line you’ve ever used… and did it work?”
- “If I dared you to flirt with me right now, what would you say?”
- “Be honest. How long did it take you to think of texting me first?”
- “Would you rather get kissed in the rain or during a movie night?”
- “What’s something totally random that always makes you smile?”
- “What would you do if I showed up at your door with snacks?”
- “Tell me the truth. How many selfies did you take before sending me that one?”
- “If I challenged you to charm me in one sentence, what’s your best shot?”
- “Ever flirted with someone through memes? Asking for… myself.”
Spicy Texts With Just Enough Sass
If you’re ready to raise the heat a little
These aren’t dirty—just suggestive enough to make things interesting. Delivered with the right tone, they spark curiosity and chemistry without crossing into cringe.
- “Careful. Keep talking like that and I might actually like you.”
- “You’re flirting a little too well. I might need to sit down.”
- “Don’t tempt me. Or do. Actually… definitely do.”
- “You’re dangerously close to becoming my favorite distraction.”
- “Flirting with me before lunch? Bold.”
- “You better be this smooth in person too.”
- “If you’re trying to get my attention… it’s working.”
- “I should warn you—I flirt back.”
- “Keep talking like that and I’ll start thinking things.”
- “If this is your version of subtle, I’m loving it.”
Flirty Comebacks to Keep the Flow Going
For when he texts first and you want to keep it flirty
Sometimes, he takes the lead—and your reply can either keep the mood alive or crush the vibe completely. These responses help you steer things without sounding forced.
- “Ooh, confident today, are we?”
- “That’s cute. Got any more?”
- “I’d flirt back, but I don’t want you falling too hard.”
- “You sure you’re ready for this level of charm?”
- “You trying to make me blush or what?”
- “I see you came prepared with that one.”
- “Are we flirting or just practicing?”
- “You’re dangerously close to getting a flirty nickname.”
- “That’s one way to get my attention. It worked.”
- “Your confidence is showing. And I’m here for it.”
Teasing Texts That Keep Him Guessing
Make him work just a little bit for your attention
Mystery is part of the charm. These texts are playful, fun, and full of just enough bait to keep him chasing.
- “I was going to tell you something, but now I’m not sure you’ve earned it.”
- “You think you’re charming… prove it.”
- “I’ll give you a compliment—but only if you impress me first.”
- “Guess what I’m wearing. (Nope. Not telling.)”
- “You’re definitely in my top 5. Of what? Hmm. Can’t say.”
- “You don’t get the flirty version of me until you pass the test.”
- “Keep texting. I want to see where this is going.”
- “I’m trying to decide if you’re worth a goodnight text.”
- “Your message was cute. Almost cute enough for a selfie.”
- “You’re giving main character energy today.”
Late-Night Flirty Starters
For those after-dark convos that lean into chemistry
You’re both up. The vibe is chill. The lights are low. These are the texts that stir the pot just enough to make the conversation linger.
- “You up or just pretending to be mysterious?”
- “Not gonna lie. I was hoping you’d text tonight.”
- “I always text you when it’s dark. Must be the mood.”
- “Can I send you a flirty thought or should I behave?”
- “I had options tonight… and here I am texting you.”
- “What would you do if I said I was bored and cute right now?”
- “Should we be texting this late? Probably not. So let’s keep going.”
- “I’d say ‘sweet dreams,’ but I might be in them.”
- “Nighttime me is bolder. Just warning you.”
- “Tell me something that’ll keep me awake… in a good way.”
One-Liners That Work Anytime
Save these for when you need a go-to
Some days you just want a quick spark. These texts are like matchsticks. Strike one and see what happens.
- “Just thinking about how cute I am. Also you.”
- “Stop being so charming. It’s distracting.”
- “You get bonus points for texting me first.”
- “Why are you not texting me right now?”
- “You like teasing me, don’t you?”
- “I should probably stop flirting with you. But here I go again.”
- “This convo could either be fun or dangerous. Your move.”
- “What would happen if I called you right now?”
- “You talk a big game. Let’s see if you can keep up.”
- “You’re lucky I’m in a flirty mood today.”
Tips for Keeping the Flirt Alive
Flirty conversations lose their magic when they turn one-sided or get stuck in a loop. The goal isn’t to impress—it’s to create a rhythm. Be playful, but also listen. If he’s matching your energy, keep going. If not? Pull back or pivot.
Use emojis like spice—not the whole dish. A wink or smirk can go a long way, but don’t flood the message like you’re in emoji jail.
And if something feels off or forced? Trust that instinct. A good flirty convo should feel light, not like homework.
When to Switch It Up
Not every flirty text has to turn into a full-blown conversation. Sometimes, one clever message is enough to keep the spark going. If he doesn’t reply right away, don’t sweat it. Give it time. And when in doubt, take the vibe offline and suggest hanging out in person. That’s where the real sparks fly anyway.
Final Thoughts
The best texts aren’t the ones that sound perfect—they’re the ones that sound like you.
Let your personality show.
Be a little unpredictable.
Make him wonder what you’ll say next.
Because half the fun of flirting is keeping him on his toes.