105 Text Conversation Starters

Texting shouldn’t be this hard, but sometimes, it totally is. Like, do you go with a casual “Hey”? A quirky joke? A deep question about life at 10 PM? (Been there.)

That’s where this little cheat sheet comes in. I’ve put together a bunch of easy, natural, not-cringey text conversation starters for every kind of situation. Go ahead, steal a few. I won’t tell!

First Texts to Break the Ice

1. Hey! How’s your day going so far?
2. I just realized we never really got to chat properly. How’s everything?
3. Random question: What’s your go-to comfort food?
4. I saw something today that reminded me of you (in a good way, promise).
5. What’s something fun you’ve done recently?
6. I’m in need of a good show to binge. Any recs?
7. I heard this song and thought you might like it too.
8. You seem cool, so I figured I’d say hi before overthinking it.
9. Coffee or tea person? This is important.
10. What’s the most random thing you’ve Googled lately?
11. Do you usually reply fast or just when you feel like it? No judgment.
12. What’s one thing you actually enjoy doing alone?
13. I’m trying to be more social—so hi, how are you?
14. What’s your idea of a perfect weekend?
15. I’m the worst at texting first, but here we are.

Friendly Starters to Keep in Touch

1. Hey, you! How’s everything going lately?
2. Just checking in. Felt like catching up.
3. What’s something you’re looking forward to this week?
4. I miss our random convos. Got time to chat?
5. It’s been a minute! What’s new with you?
6. Can we pretend we’ve been texting non-stop and skip the awkward gap?
7. I saw this and thought of you—had to send it.
8. What’s a small win you’ve had recently?
9. Any life updates I should know about?
10. I was just remembering that one time we couldn’t stop laughing.
11. Felt like talking to someone familiar. How are you holding up?
12. How’s your mental space these days?
13. We don’t talk as much, but I still appreciate you.
14. I’m low-key craving a catch-up session. Up for it?
15. Let’s bring back our tradition of texting about random stuff.

Funny and Playful Openers

1. If we were stuck on a deserted island, what would you bring (besides snacks)?
2. Be honest—how many alarms do you set in the morning?
3. I just made the most questionable food combo and I need validation.
4. What’s the weirdest dream you’ve had recently?
5. I feel like you have chaotic energy… in the best way.
6. If we switched lives for a day, who would crash first?
7. Would you survive a zombie apocalypse or just trip on day one?
8. Okay, serious question: Pancakes or waffles?
9. What’s your most random talent? I’m talking party trick level.
10. I once tried to microwave eggs. How’s your day going?
11. What’s your spirit animal when you’re hangry?
12. You have 30 seconds to impress me with a meme. Go.
13. Describe your mood today using only emojis.
14. What’s a completely useless fact you can’t forget?
15. I feel like we’d either be best friends or get banned from places together.

Flirty Conversation Starters

1. So, who usually texts first—you or me?
2. I feel like we’d be dangerous together… in a good way.
3. You’ve been on my mind today. Thought I’d let you know.
4. What’s your idea of a perfect date night?
5. Just wondering… how are you still single?
6. If I sent you a good morning selfie, would you rate it?
7. I swear you’re the kind of person who makes texting fun.
8. I’m bored and slightly cute. Should we talk?
9. Can I be honest? I like talking to you.
10. On a scale from 1 to 10, how good are you at flirting over text?
11. What’s one thing you find attractive that most people don’t expect?
12. If we were out right now, where would we be?
13. Just a casual reminder that you have a great smile. (Yes, I noticed.)
14. I’m in a playful mood—can you keep up?
15. What’s something cute you’d never admit in person?

Conversation Starters for Someone You Just Met

1. I don’t know much about you yet—what’s one thing I should?
2. So what’s your vibe: Early bird or night owl?
3. What do you usually do for fun?
4. What’s something totally random you’re into?
5. What’s your go-to comfort activity when you’re feeling off?
6. Are you more of a homebody or always out and about?
7. What’s something you’d recommend everyone try at least once?
8. Ever had a super unexpected talent or hobby?
9. What kind of music puts you in a good mood?
10. Are you more spontaneous or a planner?
11. If you could live in any city for a year, where would it be?
12. I’m trying to guess your personality based on your vibe—help me out.
13. What’s something you’re into that people wouldn’t guess?
14. How do you usually spend your weekends?
15. Is it weird that I’m actually enjoying this convo?

Conversation Starters When You’re Bored

1. What’s the most random thing you’re thinking about right now?
2. Wanna play a quick this-or-that game?
3. I’m bored. Distract me with something funny.
4. What’s your go-to “I have nothing to do” activity?
5. If you could be anywhere else right now, where would you be?
6. What’s a movie you’ve watched more than five times?
7. Wanna trade weird facts for a bit?
8. What’s your ultimate snack combo?
9. If we had superpowers, what would our duo name be?
10. What song instantly changes your mood?
11. What’s something totally random you wish you were good at?
12. Should we create a fake business idea just for fun?
13. What’s the weirdest trend you actually kinda liked?
14. What’s a childhood TV show you secretly miss?
15. I’m low-key just texting to cure boredom—hope that’s okay.

BONUS: Follow-Up Texts to Keep the Conversation Going

1. That reminded me—have you ever…?
2. Wait, I didn’t ask. How did that thing go?
3. You left me hanging with that last reply, haha.
4. Okay, now I’m curious. Tell me more.
5. I’ve been thinking about what you said earlier.
6. Not to be nosy, but that sounded interesting.
7. Also, totally forgot to ask this last time.
8. I had to circle back to this because it’s too good.
9. Can we go back to that convo from before? It stuck with me.
10. Speaking of that… I just saw something similar.
11. I love where this is going. Mind if I keep it going?
12. That reminds me—what’s your take on…
13. It’s been a few days, but I didn’t forget our chat.
14. Your last message low-key made my day.
15. Before I forget—thanks for that, by the way.