50 Flirty Conversation Starters to Break The Ice

Cracking the online dating code is hard.

But guess what? 

It gets a lot easier if you nail the opening line.

Conversation starters are basically the cheat codes of online dating. If you can grab someone’s attention with your icebreaker, you’re halfway there to a first date.

In this article, we’re going to run you through 50 of the best (and flirtiest!) conversation starters. 

50 Flirty Conversation Starters to Break The Ice

1. “Okay I’ll make the first move when it comes to sending the first text. What will your first move be?”

Wow. With this fireball of an opener, you’re inviting all kinds of flirty answers! Will they be the first to set a date? The first to kiss?!

2. “I’ve already waited 6 hours to talk to you – my heart can’t wait any longer.” 

Of course, your heart can wait longer (because you’ve never met, duh). But this is a really cute, flirty opener that might even melt their heart. 

3. “Damn, I matched with you because I thought you were the same person I bumped into yesterday. Turns out you’re another hot person on this planet.”

There’s literally no shame in greasing the wheels with a cheesy compliment like this. 

4. “You’re sending so many mixed signals by matching me but not sending me a message. So naughty of you.” 

Making the other person appear to be the naughty one is always a winner when it comes to dating, both online and offline. 

5. “I cannot believe you’ve held off messaging me for so long. You deserve a medal.” 

Does cockiness always work? Nope. But a cocky opening message like this will make most people grin. 

6. “I had a dream that you messaged me! Now I’m sad.” 

I mean, obviously, this isn’t true. But it’s still guaranteed to get a flirty message back (from most people at least). 

7. “If we have time to match, we have time to chat. Let’s sort it out.” 

This is one of my personal favorites. Each time I’ve used it, I’ve almost always got a “damn, you’re right,” message straight back. Nothing works better than making the other person feel a tad guilty for something they didn’t even do! 

8. “I’ve not seen you in FOREVER! Literally.” 

Hilarious. Literally. 

9. “Did you smile as much as I did when we matched?”

I’ll level with you – this is a pretty smoochy opening line that you should only use on someone you’re REALLY into. 

10. “Hey, I just woke up and decided you’d be the first person I texted today. And maybe the last at night. If you want that.” 

Same deal as above. 

11. “Should I open with a joke, a pick-up line, something cheesy … or just ‘Hey’?”

Giving them a choice like this works so damn often it’s not even normal. Naturally, you need to have jokes, pick-up lines, and something cheesy lined up. 

12. “It’s been two days since we matched, I feel like you’ve forgotten I exist.”

It’s corny, but it’s flirty – and it can really work wonders in making them feel bad that they reply to you. 

13. “I’m starving. Just tossing some first date ideas out there.” 

Wanna set up a date as soon as possible? This kind of opening line makes your intentions clear. 

14. “Still single, three days after we matched. Just so you know.” 

This is an easy way to elicit a “me too” response – and then you can take things from there. 

15. “Hey you.” 

I mean, some people might see this as being a tad creepy if they don’t get the flirty/humorous undertones. But sometimes it really works. 

16. “Reckon we matched in a past life? You look familiar.” 

OBVIOUSLY, dating apps didn’t exist in your previous life. But that’s what makes this icebreaker such a killer. 

17. “Just stuck Netflix on but wondering if talking to you would be more entertaining.”

The thing with this opening line is that it lays down a challenge to them. Will they rise to it? 

18. “My dating app will apparently self-destruct unless you reply to me. That's what I got told anyway.” 

Will they save you from online dating oblivion?!

19. “My dog was so happy when we matched.” 

All girls love dogs! Using this A-star opening line is essential if you actually have a dog (and it always helps if you have a dog pic in at least one of your pics). 

20. “Literally just heard a song on the radio that describes our situation right now so perfectly.” 

A song about two people who’ve matched but not chatted yet? Brilliant.

21. “Level with me. You’ve been checking your app constantly to see if I’ve texted, right?”


22. “Would love a text back so much that even an emoji would work right now. A cute one.” 

It can be her way of showing she’s interested in you! 

23. “I dreamt that I opened with a killer line … but then woke up and all I’ve got now is ‘hey.’” 

You just know she’s gonna try so hard to make you remember what you said to her in your dream. 

24. “I’ve got an extra ticket. Interested?” 

Extra ticket to what?!

25. “I don’t know what it is with me. I’m always the one who starts a conversation and the other person always ends it.” 

Self-deprecating humor always wins. 

26. “If you could choose an emoji to describe what you felt when we first matched, which one would you choose?” 

This could get a bit naughty. 

You can check this amazing list of Flirty Questions to ask a girl because questions help you break the ice and keep the conversation flowing.

27. “Look at me, ma, I’m sending the first message, ma!”

If she doesn’t get the movie reference, this opener will be a dead-end. So only use it if she’s already written on her bio that she’s really into movies. 

28. “Just had to put on some clothes to send this opening message. Because I’m a gentleman.” 

Ooft. But maybe she’d prefer it if you hadn’t bothered to dress? 

29. “Do you ever text first? Or do I make you nervous?” 

This is a great way to encourage her to be bold enough to send you a reply. 

30. “Can you help me with a problem? I need to get off this dating app.” 

I mean, this is probably as smooth as conversation starters go. How can she say no to this? Lend a guy a hand! 

31. “We matched ages ago. Should we just skip to the first date now?”

After all, no one wants a pen pal, right? 

32. “My biggest deal breaker is a girl who doesn't reply to my opening message.”

Obviously, she won’t get a date with you if she commits your dealbreaker! The choice is hers. 

33. “Do you believe in love at a first match?”

Naturally, no one actually believes in love at the first match. But this is still a cute way to get someone to shoot you a reply, especially if she says on her bio that she’s looking to settle down. 

34. “Rate my opening message out of 10 please.” 

She might say it sucks – but that can still spark a conversation. And hey, she might giggle at your lame attempt (which is also cool). 

35. “If we went on a date based on the interests in our profiles, where would we go?” 

I really like this opening line. It’s not too serious but it helps you to both visualize being on a date together, which sets the scene for some flirting. 

36. “I literally had a dream that we would match.” 

Way to woo a girl. If she’s game, she’ll ask “what happened next?”

37. “Well damn, I didn’t join to find my soulmate. But you’ve got me rethinking.” 

Only send this if you're truly serious about looking for love online. If you’re just looking for a pick-up, go with something else. 

38. “I’m surprised you matched with me. They say I’m trouble …” 

This is a GREAT way to arouse her curiosity. 

39. “Hey, sorry I haven’t sent the first message until now. I tried texting you but it turns out I haven’t got your number.” 

Ha. Funny. 

40. “Admit it. When you saw you had a new message you were hoping it’d be from me.” 

She won’t admit it. But it’s probably true. 

41. “Fine, I’ll send the first message if you send the second. Do we have a deal?”

She can confirm or deny it. 

42. “I usually send dirty icebreakers. But you’ve already turned me into a gentleman.” 

Again with the flattery. Works every time. 

43. “Do you prefer matching or talking?”

Everyone prefers to chat, right? 

44. “Out of all your matches, none of them can juggle with fire like I can.” 

It’s a bold statement – and one that’s guaranteed to catch her attention. 

45. “I think we should both try something new today! Like talking to each other.” 

I’ve always said that people should be willing to do something different every day. 

46. “You’re my 33rd match. 33 is my favorite number. It means something.” 


47. “So, you’ve matched with me. Congrats. You have completed online dating.” 

To be fair, this flirty text could come across as too arrogant to some girls. But if she replies, just make sure to tone it down a little with your next messages. 

48. “What’s your idea of a perfect match?”

Let’s see if you’ve got what she’s looking for. 

49. “Haven’t heard from you yet! Wanna match on another app and see if we have more luck there?”

Worth a try. 

50. “I mean, we can't set up a date until one of us talks.”


These are 50 flirty conversation starters that you can use to kickstart a conversation with your dating site matches. You can copy and paste them if you like or you can make a few tweaks. Whatever you decide to do, make sure to check out our other articles that will help guide you through what to do next. Because – after all – a conversation starter is only the start of things.

About Will Titterington

Will is a writer, coach and life lover who enjoys helping people reach their potential. Will has plenty of experience with Online Dating. He loves to test different apps and sites and share his experience on DatingXP. He loves art, sports, connecting with new people from all over the world, and making people laugh.