Photo by Andrea Piacquadio

Flirty conversation starters can make all the difference in how you’re going to be perceived by your crush.

First impressions matter a lot.

This is why it’s a great opportunity to shine by charming them with a creative text or a unique joke.

This way you can be sure, you’ll come across as confident, funny and ultimately very attractive.

Good flirty questions are all about striking the right balance between making your intentions clear and keeping things light and playful.

To help you out with navigating these sometimes tricky waters of ambiguous social interactions, I’ve put together a list of unique teasing icebreakers.

You’ll only find the crème de la crème here.

Using them will inevitably charm your crush and make them want you more.

All the conversation starters from this post can be used as a text message.

However, I’ll have a separate category for the ones suitable to be used in person too.

Here are the types of conversation starters you’ll find in my list:

  • Funny Flirty Conversation Starters
  • Deep Flirty Conversation Starters
  • Flirty Conversation for Her
  • Flirty Conversation Starters for Him
  • Flirty Conversation Starters in Person

Funny Flirty Conversation Starters

Ice beakers listed here are bound to make anybody laugh.

These are the funniest one-liners and jokes to charm your crush and make them fall for you.

You can absolutely use them to start a conversation with both a girl or a guy over text.

Some of them, are a series of text messages you can send to playfully flirt and let your crush gradually warm up to you.

1. Can I have your picture, so I can show Santa what I want for Christmas?

2. Baby, if you were a fruit, you’d be a fineapple.

3. Are you a keyboard? Because you’re my type!

4. What did the chocolate syrup say to the ice cream? “I’m sweet on you!”

5. I’ve been thinking… If you’re hotter than me, then that means I’m cooler than you.

6. -Knock, knock. -Who’s there? -Wendy. -Wendy who? -Wendy you think we can go on a date?

7. Not even Snape could Severus apart.

8. Would you rather wrestle in a pool of jello or chocolate pudding?

9. Describe yourself in one emoji. I’ll go first: 👑

10. What’s one thing that never fails to make you cringe?

Deep Flirty Conversation Starters

The icebreakers in this category will not only make your crush fall for you more, they’ll also let you two feel closer and more emotionally connected.

They’re great for starting deep conversations. A more serious and meaningful interaction is bound to follow suit!

They’re actually great to use as a text message, as well as in person.

11. What’s hiding behind that sweet smile of yours?

12. Tell me a quality you’ve been looking for in a partner, that I actually possess?

13. Fun question for you: What movie title best describes your life at the moment?

14. I would really love to know what inspires you right now.

15. What are you like when you let go?

16. What small things make your day better?

17. When I look in your eyes, I see a very kind soul.

18. What was the last song you’ve listened to?

19. What is something about you that’s irresistible?

20. What are you looking for in a relationship?

The last question here is a good way to challenge your crush.

If you want to find how to best use it, check out this post: “What Are You Looking For in a Relationship” Is a Test – How to Answer

Flirty Conversation for Her

When starting conversations with a girl, it’s generally better to avoid being too direct or sexual.

Women like to be teased and romanced. They also love receiving compliments, or being asked about their thoughts or preferences.

The icebreakers here will make any girl interested in you.

21. It’s girls like you that cause global warming!

22. I just saw the new picture you uploaded. Looking hotter than ever, I see.

23. What qualities does a man need to have before you’ll go on a date with him?

24. I can’t figure out if I should start this conversation with a compliment, a horrible pick-up line, or a simple “hello.” You choose.

25. Is your name Summer? ‘Coz you’re HOT!

26. What food do you crave most often? Maybe we could go get it together sometime?

27. Be honest. How long have you been waiting for a text from me?

28. Is it cocktail o’clock yet?

29. I’m thinking about deleting Tinder, because I’ve already found the girl I want to be with.

30. FYI. We’re hanging out tonight. And if not tonight, then tomorrow.

Flirty Conversation Starters for Him

On the contrary to women, when flirting with a man, being direct and making sexual remarks often works very well.

Guys can be extremely oblivious to girls showing interest in them. This is why it’s so important to make your point impossible to miss.

Just like women, men love to be showered with attention and complimented.

These conversation starters will make any guy interested and want more from you.

31. If kisses were snowflakes, I’d send you a blizzard.

32. I had a dream about you last night. I’d tell you what happened, but it’s way too inappropriate.

33. We should go out for coffee sometimes because I definitely like you a latte.

34. Do you fish? Because you have me hooked.

35. You must be a very important textbook passage, because seeing you is the highlight of my day.

36. Oh by the way, I’m wearing that smile you gave me.

37. Just wanted to personally thank you for liking my Instagram story…

38. Tell me something about you that you want me to know.

39. I’m no scientist, but I think we’re going to have pretty good chemistry.

40. Do you like girls who make the first move?

If you’re looking for with even more ideas of what to text a guy to get him to want you more….

I’ve got you covered with 50 Flirty Texts to Make Him Think About You All Day Long

Flirty Conversation Starters in Person

Starting an in person conversation with a sexy stranger can be daunting. It’s all about being playful, charming and keeping things a little vague.

Keep in mind, we’ll all awkward and desperate at times. Plus, dating should be fun and games.

Being the brave person who is daring to break the ice will only make you seem more attractive to any potential partner.

41. Hi, I’m writing a phone book, can I have your number?

42. There must be something wrong with my eyes—I can’t seem to take them off of you.

43. You look like you know how to have a good time. Been on any adventures lately?

44. I’m afraid my flirting skills are a bit rusty. Would you mind if we practiced together?

45. I was just trying to buy a drink here, but you’re very distracting.

46. I’m not sure what it is yet, but something about you seems fascinating.

47. Your hand looks heavy, can I hold it for you?

48. Hi! I have a quick question… Do you believe in love at first sight, or should I pass by you again?

49. I seem to have misplaced my phone, could you give me a ring?

50. I need some advice. There’s someone I want to ask out here, but I’m not sure how…

And if you want to be sure you’re really prepared for an in person exchange, check out these 10 Unique Questions for a Perfect Date.

Thank you for reading, and if you want to share your best flirty conversation starters, be sure to drop them in the comments section!


Karolina Bartnik