27 Ways to Spark a Fun Text Conversation

woman texting

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Hannah Berman
Hannah Berman175

Sometimes, when you’re desperate to speak with someone specific, it can feel difficult to find the perfect words to start a conversation. You don’t want to come on too strong, but you also don’t want to ask a question that won’t prompt a response. It’s a difficult balance to strike, made worse by the fact that you certainly can’t just ask them “What’s up?” since the conversation that ensues will likely bore you both. 

So, what are some good conversation starters? Below you'll find a bunch of lines that you can feed to people in different areas of your life with whom you're interested in conversing; use any of them to kickstart a killer convo!

New friends.

1. Who’s your fav author? Looking for book recs!

This line is great because it helps you to get to know your friend better, and also produces a topic that you can bring up multiple times as you read their recommendations.

2. PLEASE tell me you’ve heard the news about [something you both care about].

If there’s news worth sharing, letting a possible new friend know that you’re thinking of how they’ll react to it is a good way to strengthen your bond. 

3. Have you seen Friends? I feel like you remind me of [insert character name].

As long as you don’t say "Ross," this line is sure to reinforce the friendship you’ve begun to build with your intended subject. Feel free to substitute any other TV show or film, of course.

4. What’s your pet peeve?

It’s good to know so that you don’t ever end up accidentally annoying them!

5. What’s your favorite ice cream flavor?

This line makes it really easy to propose a trip to the local ice cream parlor down the line.

6. I feel like we need to figure out if we’re astrologically compatible. When’s your birthday?

There comes a point in any friendship when you need to check if your bond was meant to be, so there’s no time like the present. Asking for someone’s astrological sign helps build a friendship for two reasons: first, you’ll know when their birthday is coming up, and second, it offers a wonderful opportunity to discuss whether or not you believe in all that star mumbo-jumbo.

Old friends you want to reconnect with.

7. I think I just saw [insert high school acquaintance’s name] on the street! 

This line will prompt a discussion of a character from your shared past — you can expect questions along the lines of “How did they look? What did they say to you?” in response, and from there, you can transition to catching up. 

8. What’s your deal this summer?

Getting in touch with an old friend over text is nice, but hanging out in person is even better for catching up. Ask this question if you’re interested in finding out when your friend is free and perhaps getting together. 

9. Remember when you…?

If you’re thinking of getting in contact with an old friend, sharing a sweet memory with them is a great way to reconnect. Even if they don’t remember the moment you bring up, they’ll appreciate that you do it.

10. Hey, do you still have that recipe for [something] that we made [specific day]?

Asking an old friend for something specific is a great way to relive a memory and ensure a response at the same time. Plus, maybe you’ll get a fun baking project out of it.

11. I’m back in town! Any suggestions for old haunts I should visit?

Instead of providing a shared memory yourself, this line puts the onus on your old friend to bring up an old memory and reminisce. You can commiserate about your favorite restaurants that are now closed and learn which spots from your past were really important in the eyes of your friend.

People you want to date. 

12. What’s your favorite board game?

Whether they love Settlers of Catan, Monopoly or Cards Against Humanity, this line will start a heated, flirty debate over the merits of each game — and the excuse to propose game night.

13. Big spoon or little spoon?

Flirty, coy and important to know for future reference.  

14. [picture of dog] Thinking of you! 

Dogs are perhaps not the most sensual animal, but sending a pic of the right pup is better than texting “You up?”

15. What’s your favorite type of food?

Once you have this essential info, you can probably finagle your way into suggesting a visit to a restaurant that serves this cuisine. (Or, if you’re feeling more frisky, suggesting a home-cooked meal.)

16. Hey, I think you should check this out! [interesting article tangentially related to something you’ve discussed]

Show off your intellectual side by sharing an article. There’s value in convincing your potential beau that you’re a true scholar!

17. What are you up to this weekend?

This line is subtle — it could be starting an idle conversation, or it could be suggesting a possible date. See where their response leads you.


18. How’s [insert project with deadline] coming along?

If you’ve paid attention to your colleague’s schedule and workload, you’re probably aware of what they’ve got going on. Hit them with this line over the weekend to let them know that you’re there if they need to vent. 

19. Thinking of bringing in cookies to the office — what kind do you like?

Imagine the smile that would spread across your face if you were to receive a text like this. Try spreading that joy to your coworker! 

20. Is your week looking free enough to grab drinks after work someday?

Reaching out to your coworker to spend some time together outside of work is a good idea if you’re interested in moving your relationship out of the work realm to a more friendly space.

21. Ugh, can’t believe how much work I had to take home this week! 

Nothing works better to bring people together than a common enemy, and being coerced into bringing your work home certainly constitutes that common enemy.  

22. Overheard at the water cooler: [insert gossip].

If there’s gossip to share, don’t keep it to yourself. Share the wealth. It’ll help you and your coworker connect and open the floodgates for more talking behind the boss’s back.

Relatives you haven’t spoken to in a while.

23. Did you hear that [insert juicy familial gossip here]?

It's still true: everyone loves gossip. Your cousin will be overjoyed to hear from you and even more overjoyed to find out the REAL reason why Aunty Lucinda missed Christmas this year.

24. I just found something that Grandma/Grandpa gave me.

If you’ve recently unearthed an artifact from your youth and you want to share that discovery, tell a relative.

25. I’m trying to trace our family tree. Do you know anything about our ancestors?

The perfect line to reconnect with your current — and past! — relatives. They’ll be sure to ask why you want to know.

26. When’s the next time you’re coming to town?

Let them know you’re interested in seeing them the next time they swing by! 

27. I feel like it’s been forever! How are things with you at work/school?

When all else fails, be honest. You want to have a conversation with them, so just reach out!

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