100 Conversation Starters for Dry Texters

It can be a real head-scratcher trying to keep a conversation going with someone who doesn’t give you much to work with. I’ve faced the same challenge, and it’s not always easy to find the right words.

That’s why I’ve put together some foolproof conversation starters that will help turn those dry texts into delightful dialogues.

These suggestions range from meaningful questions to light-hearted, fun prompts, all designed to draw out more than just a simple “fine” or “okay.” Stay tuned, and I’ll share the secrets to making every message count!

Everyday Conversation

1. How was your day?
2. Have you read any good books lately?
3. What’s the highlight of your week so far?
4. I saw a movie and thought of you. Have you seen it?
5. Do you have any weekend plans?
6. What’s your favorite way to unwind after a long day?
7. I tried a new recipe. Do you enjoy cooking?
8. What’s your go-to comfort food?
9. Have you ever traveled abroad? Where was it?
10. What kind of music puts you in a good mood?
11. Do you follow any podcasts? Any recommendations?
12. I started a new hobby. Do you have any hobbies?
13. What’s your favorite holiday and why?
14. If you could have any superpower, what would it be?
15. What’s one thing you always wanted to learn?
16. Have you seen any good TV shows lately?
17. What’s your favorite outdoor activity?
18. Do you prefer tea or coffee?
19. What’s your dream vacation spot?
20. Do you have any pets?

Building Stronger Connections

1. What’s something you’re really passionate about?
2. Do you have a secret talent?
3. What’s your favorite childhood memory?
4. What’s the best advice you’ve ever received?
5. What’s the most meaningful gift you’ve ever received?
6. Do you have a favorite family tradition?
7. What’s one thing you couldn’t live without?
8. Who is your biggest inspiration?
9. What’s your favorite family recipe?
10. What’s one thing you’re grateful for today?
11. What’s your biggest dream?
12. Do you have any siblings? Tell me about them.
13. What’s your favorite way to spend time with friends?
14. What’s a cause you care deeply about?
15. What’s the best trip you’ve ever taken?
16. What’s your idea of a perfect day?
17. What are your top three personal values?
18. What’s something you want to achieve this year?
19. Do you prefer a night out or a cozy night in?
20. What’s your favorite way to relax?

Fun and Light-Hearted Questions

1. What’s a funny thing that happened to you recently?
2. What’s your guilty pleasure TV show?
3. If you could meet any celebrity, who would it be?
4. What’s the weirdest food you’ve ever tried?
5. If you could live in any country, where would it be?
6. What’s the strangest dream you’ve ever had?
7. Do you have a go-to joke?
8. What’s your favorite meme or viral video?
9. If you could time travel, what year would you visit?
10. What’s your favorite holiday destination?
11. What’s your spirit animal?
12. Have you ever been on a blind date?
13. What’s your favorite childhood cartoon?
14. If you could have dinner with anyone, dead or alive, who would it be?
15. What’s the most random fact you know?
16. What’s a quirky habit you have?
17. Have you had any weird food cravings lately?
18. What’s the most adventurous thing you’ve ever done?
19. If you had to eat one meal for the rest of your life, what would it be?
20. What’s your favorite board game or card game?

Open-Ended Questions

1. What’s something you’re looking forward to this week?
2. How would you spend a perfect day if you could do anything?
3. What’s a passion of yours that not many people know about?
4. Can you tell me about one of your happiest memories?
5. What’s the best piece of advice you’ve ever received?
6. How do you like to unwind after a long day?
7. What’s one goal you have for this year?
8. If you could learn any skill instantly, what would it be?
9. What’s something that always makes you laugh?
10. What’s the most interesting book you’ve read recently?
11. If you could travel anywhere right now, where would you go?
12. What’s a movie that really impacted you?
13. Who in your life has influenced you the most?
14. What’s your favorite way to spend a weekend?
15. What are three things you can’t live without?
16. What’s a skill or hobby you’ve always wanted to pick up but haven’t yet?
17. What’s one of your favorite family traditions?
18. If you could have a conversation with anyone in the world, who would it be and why?
19. What’s a recent challenge you overcame, and what did you learn from it?
20. What’s the most memorable place you’ve visited, and what made it so special?

Confidence-Boosting Starters

1. I loved your last post about _____! Can you tell me more?
2. I heard you’re really good at _____. How did you get into it?
3. What’s your favorite thing to do on a rainy day?
4. You have a great taste in music! What are you listening to these days?
5. I’m curious, what’s your dream job?
6. What’s something that always makes you smile?
7. I saw this and thought of you. Do you like _____?
8. Do you have any go-to movie recommendations?
9. I’ve been getting into _____ lately. Any tips?
10. What’s your favorite way to spend a Sunday?
11. I’m planning a trip. What’s one place you’d recommend?
12. Have you tried any new restaurants lately? Any favorites?
13. Your opinion matters to me. What do you think about _____?
14. Do you have any hidden talents?
15. What’s the best book you’ve ever read?
16. I loved the outfit you wore in your last photo! Where do you shop?
17. What’s been the highlight of your month so far?
18. Do you have any favorite motivational quotes?
19. I remember you mentioned you like _____. Have you done it recently?
20. What’s the best advice you’ve ever been given?