25 Questions to Ask a Girl on First Chat to Impress Her

You’ve got her number and you’re going to text her…what do you say? Where do you start and how do you keep the conversation going? I’ve listed 25 questions that are good ice breakers to make the conversation flow.

A good place to start the conversation is always to say you saw something that reminded you of her, like say walking past a billboard advertising a movie the two of you were talking about, or seeing someone wearing the same dress as her. You can also simply say “Hey girl, you crossed my mind just now 🙂  How’s your day going?” If you want to make it even simpler “Hey, how’s it going?” works too.

Depending on your relationship with the person you can say call them lady, girl, cutie, lovely, etc. It makes it more fun and personal. You can even use sexy, hot stuff and so forth, but be sure to know they’re OK with it. Chances are they’ll be OK with it if you’ve flirted before.

What you don’t want to do is write “hey” and leave it at that. At least put in a little bit of effort, or she might very well not put in the effort to reply!

Remember to vary how you start conversations, as well as the questions you use during conversations. “How was your day?/How are you?/How’s it going?/What’s up?” is all very well, but you don’t want to ask that and only that every time you speak. It shows a lack of imagination and people will only want to answer that question so many times.

Really there are endless ways to start a conversation. Below find a few more possibilities.

  • I so have to study right now, but it was tons of fun seeing you yesterday and instead of studying I’m sitting thinking about what you said about…. (whatever funny/amusing/interesting thing she said that’s something that would stand out in your memory)
  • I just googled that thing you told me about yesterday…so weird! I can’t believe you were right! 🙂 How are you doing? 🙂
  • Hey girl, I came to think of you 😉 How’s your day going?
  • Hey! :)How are you doing? I’m totally supposed to study right now, but I thought it’d be more fun to text you… 😉

Whatever you do during the conversation, try to keep it fun, lighthearted and flirtatious, unless you’re talking about the deep stuff…then keep it deep. Compliments, innuendo, teasing, challenging…all that is part of flirting, so do it!

That said, let’s get started on the questions! The ones you ask once the conversation has gotten started properly!


1. How was your day? / How was school? / How was work?



This is the first and most obvious question when initiating contact. If you can, try to link it to something, like “How was school? Still stuck with Mr Nutcase in maths? I feel so sorry for you I’d almost opt to do your homework for you. Almost… ;)” And this is the one question you can ask to start the conversation – the rest are for once you’ve got talking!

2. So tell me one thing about yourself that I don’t already know?

Always a good one!

3. What’s one thing you’d never confess to your mother?

Often gets interesting replies…

4. Who’s one person you’d love to meet?



Is it her future husband, Britney Spears or Michelle Obama?

5. What do you think qualifies as “worst movie ever”?

Can lead to a funny discussion about horrible movies. Because they’re often so horrible it gets funny. Can also lead onto discussion about favorite movies, TV shows and books of all time.

6. Who do you think influenced you the most growing up?

Could be her mom, could be a plethora of different people.

7. Have you ever seriously read a book or seen a movie that changed your life?

If she has, that’s an interesting topic!

8. What are your main passions in life right now? What makes you happy?

Good to know for future dates!

9. Do you think you’ll ever move to another place?

Always useful to know if you want to get serious with them.

10. What are your pet peeves when it comes to dating?

You wanna know!

11. If you could go anywhere right now, where would it be?

Here you can play a game talking about what you’d do if you went to some specific place together.

12. What’s your favorite way to spend the weekend?

Will definitively give you some insight into her life!

13. What are three songs you’ll always want to have on your iPod?

Will invariably lead onto talking about music in general.

14. What are three goals that you have in life?

Goals and dreams are what propel people forward and one of the most attractive things is finding someone who understands and encourages your dreams.

15. What’s a childhood memory you have that always makes you smile when you think about it?

Will give you an insight into her childhood! And what makes her happy.

16. What are qualities you really enjoy in a friend?

Lovers are friends you have sex with. So…be her friend too. Knowing someone’s values is always helpful too. It can help you avoid unnecessary misunderstandings.

17. What was your favorite TV show as a kid?

Even TV shows shape us!

18. Who are your role models, if you have any?

It’s interesting to see what qualities she admires in people. Probably shows a lot about who she is too.

19. What’s your favorite cuisine?

Does she like Thai, or Mexican?

20. What’s one thing you’ve learnt in life that you think everyone would be better off if they learnt?

If she replies how to put on mascara you know the depth of her intellect right there.

21. What’s one thing you’ve done that made you feel totally embarrassed at the time, but now make you laugh looking back?

Can lead to an awesome and hilarious conversation!

22. What are the most attractive traits in men?

Only go down this line of questioning if you’re flirting…

23. Is there any fairytale or movie that reminds you of your own life?

Who knows, you might be dating Rapunzel?!

24. So tell me, if I were to give you any gift right now, what would you choose?

What kind of gifts/surprises does she love?

25. If I were to impress you, where would I take you?

If the two of you are flirting, this is a valid question!

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