30+ Conversation Starters For Texting That Are Better Than Hey

Attractive woman holding coffee and mobile texting her crush

There’s something about getting a “hey” for conversation starters for texting that makes you feel like a pre-teen on AOL instant messenger (more commonly known as AIM). Most of us tend to give the same energy we receive, so if we receive a “hey,” we’ll respond with a “hey” or maybe a “what’s up.” It almost feels wrong for the conversation to not devolve into, “nm u?”

Of course, these types of conversations aren’t great for getting to know each other or capturing anyone’s interest, and they probably won’t land you a date. If you’re online dating, you might have to win someone over with your text message banter, which can be challenging. 

Here’s a tip and/or challenge: never send a “hey” text. 

Personally, I rarely even respond to a “hey,” “hi,” or “hello.” I look at the text, and figure that I’ll give the person time to tell me what they want to know.

Chances are, if you’re messaging someone on an app (especially if you’re messaging a straight, cis woman), they’re getting lots of messages. You want yours to stand out from the crowd! If you’ve moved to texting, you still want to engage the person you’re chatting with and make texting fun!

Here are some conversation starters for texting that are just as cool and casual as “hey,” but actually lead to interesting conversations that’ll help you and the person you’re texting get to know each other. 

30 Conversation Starters for Texting that are Casual, Cool, and Interesting!
1. What was the best part of your day?

This is one of my favorite conversation starters for texting that takes the basic “how’s your day?” text and helps you get a more interesting answer than, “good!” 

2. How’s your day going?

That being said, this classic text isn’t ever a bad idea either. It shows that you care about their day and sounds sweeter than “what’s up?”

3. Good Morning. What’s on the agenda for today?

Another way to ask about their day, but this time in the morning. It can also be an opener if you want to ask them out for that day, because you’ll see if they’re available. 

4. What’s your week looking like?

If you’re not a big texter, this is a great way to turn texting into a date. Find out when they’re free and confirm some plans!

5. Where should we go for our first date?

Another text opener to show that you’re not looking to waste time with small talk, but this can also lead to a conversation about what they like doing, what food they enjoy, etc. 

6. Three emojis that sum up your day so far? I’ll go first…

This text is a cute way to ask how someone’s day is going, especially if you’re both not great with words. Based on the emojis they send, you can ask questions to keep the conversation going. Like, “why on earth is a whale emoji summing up your day?”

7. What’s your favorite cuisine? 

This text works best when complimented by an eye emoji so you can preview what you’re about to ask next. And what you’re about to ask next is, “I love Thai food too! There’s an amazing place on my block. When are you free so I can take you there?”

8. I hope this was your face when you saw my name pop up on your phone: *insert cute GIF or emoji here*

This is cute, flirty, and a good way to start a conversation without getting too deep.

9. Good morning! Are you a morning person?

Take the good morning text, but learn something new about the person you’re texting. After all, synchronized sleep schedules are pretty important in a relationship. 

10. It’s so nice out today! Wanna go on a walk or something?

Again, winning conversation starters for texting take a basic small talk topic and turn it into a potential date or something more interesting. 

11. Thinking about you and hope you have a great day!

If you want to text someone, but aren’t sure if either of you have time to engage right now, this is a good way to keep you on someone’s mind without taking too much time. 

12. What’s your favorite cocktail? After the day I’m having, I think I’m going to need one.

This asks a question about them while also telling them something about you. It also will likely lead them to ask why your day is so stressful.

13. You were in my dream last night. 

Good conversation starters for texting illicit a response and nobody can resist texting back, “what happened in your dream?” to this text. 

14. What’s your zodiac sign?

Say what you want about horoscopes, but it really can tell you a lot about a person. If your date only responds with their sign, ask them if they think the description fits their personality or not. 

15. Did you see [insert news item here]? What are your thoughts?

Personally, I don’t think politics make for fun flirting, so maybe try to stick to celeb-news, viral internet sensations, or something less polarizing.

16. Doing anything fun at work today? 

You probably know what they do for a living at this point, but do you really know? If they like what they do, they’ll probably love telling you about it, which wins you points!

17. Just saw your Instagram post…those donuts look amazing! How were they?

If you follow each other on social media, their posts are an easy thing to piggyback off of for conversation starters that feel natural.

18. Just saw your Instagram post…I think we might need to go back to that donut shop, this time I’m buying 😉

If you’re a little more daring, you can also piggyback off of their social media posts to ask them on a date!

19. How was your [interview/meeting/test]? 

This seems simple, but you’d be surprised how much it means to someone when you remember that they have a big thing going on that day.

20. Can you help me choose between [X] and [Y]? 

Did you know that asking people for favors makes them like you more? Plus, asking someone for their opinion makes them feel special. Ask them which tie to wear tomorrow (with pics attached), which rug to order for your new apartment, or which ice cream flavor to pick up from the grocery store. Maybe they’ll even invite themselves over to eat some ice cream with you! 

21. Hey! What’s your schedule like this week? Let’s grab dinner one night? 

Simple, direct, and to the point. Can’t go wrong here.

22. Have you heard the new [band] album? This track is my fave so far. 

This text works better if you’ve already discussed music and are on the same wavelength. If they’re into EDM and you love country, they might not even know the artist you’re talking about. 

23. This song reminds me of you *send song link*

Always adorable, and who doesn’t like music recommendations?

24. What’s your guilty pleasure? I’m not ashamed to admit that I’m watching The Bachelor right now. 

Interesting questions seem to work best and come off more casually when you also insert a tidbit of information about yourself, like this. 

25. You just crossed my mind and I thought I’d say hi 🙂 

While this doesn’t actually say much more than the basic, “hi” text, it’s way cuter and will definitely get you a better response.

26. You look so good right now. I can’t see you, but I just know that you do, cuz you always do 🙂

This is a fun, flirty text to send that will certainly put a smile on your date’s face.

27. Send me the last meme you saved on your phone. It’s for science. 

Get a window into your date’s sense of humor while being a bit cheeky.

28. BTW, do you prefer texting or calling? 

Who knows? Maybe your date hates texting as much as you do and would rather talk on the phone or Facetime? You’ll never know until you ask.

29. Can’t stop thinking of how cute you looked in [item of clothing they wore on your last date]

This is a surefire way to make your date feel good and be more comfortable texting you first. 

30. *GIF*

If you’re really shy and stumped on what to say, just type “hi” into the GIF search bar and see what comes up. Find a cute GIF and send it. It might not be one of the best conversation starters for texting, but it’ll at least be better than a “hey” text. 

Ashley Uzer

Ashley Uzer is a freelance writer who specializes in sex and dating. She has written for many international outlets including Bustle, VICE, & Galore. She’s currently doing the whole digital nomad thing, but you can find her in Washington D.C. or NYC every once in a while. Follow along with her adventures on TwitterInstagram, or on her blog.

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