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Flirty Conversation Starters to Help Break the Ice

A guy using one of these flirty conversation starters looking at a woman on the beach and smiling.

You like someone. The cute girl you make small-talk with at the office printer. The blue shirted guy at the bar with the knock out smile. The nice guy you grew up with, who you’ve started to see in a whole new light. Or the hot girl you matched with online who shares your love of dogs. You wonder: do they like you too? And if they don’t yet, could they?

When you’re into someone, it can be a tricky dance at first. You want them to know you like them, but you don’t want to expose yourself to potential rejection and embarrassment. Well, you have two choices:

  1. Wait for them to be spontaneously enlightened about how into them you are.
  2. Extend a flirtatious olive branch and open up a window of possibility.

Here are six flirty conversation starters you can throw into everyday conversations, either online or in real that, that are suggestive enough to spark romance, but safe enough to protect your dignity.

1. Give a compliment on their appearance.
What you mean: I want to see you naked
What you say:
“That shirt looks fantastic on you.”
“Wow, your eyes are amazing.”
“Well with arms like yours…”

Complimenting someone’s appearance says you see them as an attractive being, and puts a sexual spin on whatever is between you. And if it turns out they’re not into you, you’ve done no wrong in dishing out a genuine compliment.

2. Ask if they’re attached.
What you mean: Tell me you’re single goddamit.
What you say:
“Did you go with your girlfriend?”
“I’m sure your partner would…”
“If you were single then…”

You’ll assess their availability fast since they’ll correct you if they’re not taken. It’s also flattering, as you’re basically saying they’re so fab they should have someone. If they turn out to be off the market, well, then you were right; no biggie.

2. Say you’ve been thinking about them.
What you mean: I think about you when I’m not with you.
What you say:
“You were in my dream last night.”
“I thought of you the other day.”
“I’ve been waiting to tell you that…”

When someone discovers you’ve been thinking about them, they’ll be all sorts of intrigued—so much so that they’ll probably start thinking about you back. They might wonder if you’re into them, and consider the possibilities. And if they’re not keen, they never need to know why they were on your mind; thank goodness.

4. Mention things you could do together.
What you mean: We could have so much fun.
What you say:
“Is it cocktail o’clock yet?”
“I love to dance, but I haven’t gone in forever.”
“I’m on a mission to try every burger in the city.”

From jazz to hikes, let them know you’re into fun stuff, so they can imagine being your partner in crime. It could be the first time they’ve visualized you doing a date-like activity, and once they know what you’re into, they can put together the perfect plan for your first date. If they don’t think of you that way, then they know more about you now; so what.

5. Talk about dating and being single.
What you mean: I am ripe for your picking.
What you say:
“I was out with my single pals last night when… ”
“I just went on the weirdest first date there.”
“The dating scene in this city is nuts.”

This says you’re out and about in the dating world. If they haven’t thought of you romantically, they will now. It signals your eligibility and gets the other person curious about how you would be on a date. If you’re not the one for them, don’t sweat it. Hey, they might even try to fix you up with someone; win win.

6. Offer to be their date.
What you mean: Ask me out already.
What you say:
“Well if you need a date you know where I am.”
“Do you have a plus one?”
“Sounds like a blast. I’d love to do that!”

With this tactic, you’re boldly suggesting you’d like to do something with them. They’ll be impressed with your forwardness and may be confused whether it’s friendly or romantic. (And a little intrigue can be quite the aphrodisiac.) If they want to date you, you’ve just made it easy for them. If they don’t, you can act like it was platonic; easy.

Drop one of these flirty ice breakers into conversation each time you speak, or ramp it up and use a combination of them in one interaction. They’re sassy enough to get someone thinking, but ambiguous enough to keep them guessing.

But their response is key—don’t be taken aback if their first reaction is underwhelming, or not what you hoped for. The chances are it’ll sink in when you’re apart, so stay optimistic, and monitor closely what changes in their demeanor and attitude towards you next time you’re together.

If they start avoiding you or they make it clear they’re not interested, then it’s time to back off. And if they’re not getting the hint and are impossible to read, or if the ice breakers feel like a lot of hard work, then take a hammer to the ice and ask the lucky person out. Life’s too short for missed opportunities. Happy flirting.

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