With over 23 billion text messages sent daily, it’s safe to say that texting has surpassed phone calls and e-mails in our daily lives. But texting doesn’t have to be tedious or brief.

Replace the mediocre “Hey” or “What’s up?” with one of these 110 intriguing questions or prompts to create a more meaningful discussion.  

Best Conversation Starters for Texting

Statistics say that more than 60% of people read their texts within 5 minutes of receiving them. But how many get a response? Here’s how to stand out in their inbox and dig more profound than the regular “Hey, how are you?” 

  1. What’s the best part of your day so far?
  2. Working on anything exciting at the moment? 
  3. What do you have planned this weekend?
  4. You won’t believe what just happened!
  5. What’s your opinion on _______?
  6. Did you see that viral [meme, social media post, video]? What did you think?
  7. How would you describe yourself in 3 words? 
  8. Would you choose a road trip or a resort vacation? 
  9. What food are you craving right now? 
  10. Can you help me choose between Thai and Italian food? I can’t decide 🤪
  11. What would you rather have: unlimited money or unlimited time? 
  12. What motivates you? 
  13. What’s your astrological sign?
  14. Who is your biggest role model?
  15. What was your first concert? 
  16. What are your top 5 bucket list activities?
  17. What is something people do that drives you nuts?
  18. What was your dream job as a kid?
  19. What’s the most exciting thing you’ve read recently?
  20. What do you love and hate about technology?
  21. If you could time travel, what era would you revisit? 
  22. What is something trendy that annoys you?

Having great conversation skills can be one of the best ways to connect over text. Knowing what to say is one element, but knowing how to continue a conversation and end it on a high note is a skill you can take with you for life. Here’s how!

Communicate With Confidence

Do you struggle with small talk? Do you often run out of things to say or feel awkward and self-conscious in social situations? Our Conversation Mastery Course teaches you the secrets of master conversationalists and gives you the skills you need to have confident, engaging, and captivating conversations with anyone, anywhere.

Conversation Starters for Couples Texting

A short and sweet text is a great way to let your significant other know you’re thinking of them throughout the day. You can use the opportunity to check in on how they’re doing, wish them luck on a specific activity, or bring a much-needed smile to their face (if you know they’re somewhere they don’t want to be). 

  1. How is your day going, and how can I improve it?
  2. Remember that one time we ______?
  3. How did your [class/interview/meeting/event] go? I can’t wait to hear about it!
  4. Good morning beautiful/handsome! What are you looking forward to today?
  5. What’s an emoji that sums up your day? 
  6. What was your first impression of me?
  7. Here’s your daily reminder that you are the smartest, cutest, funniest person I know. I’m so grateful to have you in my life. 
  8. Your ambition/creativity/zest for life inspires me so much. What’s your secret? 
  9. What song do you have on repeat today?
  10. I miss you. I saw [your favorite food/car/place] and thought of you earlier. 
  11. What was one of the best moments of your life so far? 
  12. I have so much to do, but I keep getting distracted thinking about you.
  13. So what’s your guilty pleasure?
  14. What have you been craving lately?
  15. Waking up to you was the best part of my day. I can’t wait to see you after work.
  16. What is the most romantic thing you’ve always dreamed someone would do for you?
  17. What’s the best compliment someone has ever given you? 
  18. What do you want most in a relationship?
  19. What would it be if you could change one thing about our relationship?
  20. Just curious: what’s the best way to cheer you up when you’re in a bad mood?
  21. I can’t wait until the next time we _______. 
  22. Do you want a foot or back massage tonight? 

Pro Tip: Send a random photo of something that reminds you of them. Whether it’s a car they like, their favorite flower in bloom, or a restaurant menu they’d love, sending pics via text is a great way to initiate a thoughtful conversation. 

Conversation Starters for Texting Your Crush

Your heart leaps when their name appears on your phone, but you never quite know what to send to get a text convo flowing. Complimenting your crush, making a flirty implication, or making plans are great ways to start. 

  1. Hey! Let’s get together—when are you free?
  2. I finally checked out the recommended show, and I’m addicted now. How do you already know me so well?
  3. I just discovered a new [their favorite food] spot. Want to join me this weekend? 
  4. What are you doing this weekend? Besides hanging out with me, of course.
  5. Is it just me, or did we knock that first date thing out of the park? 
  6. Guess which emoji I put next to your name on my phone? 
  7. What’s your favorite movie and why? 
  8. You are so cute. I’d love to hang out sometime.
  9. Hey, gorgeous/handsome. How the heck are you still single? 
  10. I have an extra ticket to [concert/festival]. Want to come?
  11. Beer and burgers or pasta and wine? 
  12. (Send a YouTube or Spotify link) This song just reminded me of you.

Flirty Text Conversation Starters

Whether you’re messaging on a dating app or sending the first message after getting someone’s phone number, a flirty text is the easiest way to make the first move. Don’t be afraid to be creative, quirky, or a little forward. Many people are willing to text things they may not say out loud. 

  1. What do you have planned for this Saturday? Can I be part of those plans? 
  2. I can’t get your smile out of my head.
  3. Has anyone ever told you that you look like [attractive celebrity]?
  4. My phone has only 5% battery, but I’m using the last of it to text you.
  5. Watching a movie and the main character looks just like you… except obviously not as cute.
  6. Can we skip the small talk and go straight to flirting?
  7. You’re killing me with these Instagram selfies you keep posting. Where did you take that most recent one? 
  8. What emoji reminds you of me? 
  9. Netflix and chill or movie date?
  10. I have Netflix on, but nobody to snuggle with. Can you help me out?
  11. What did you dream about last night? 
  12. You’ll never guess what I dreamed about last night.
  13. I can’t wait to kiss you again.
  14. Do you prefer foot massages or shoulder massages? 
  15. It’s cold out today. Can I come warm you up?
  16. I have an oversized, cozy hoodie with your name on it.
  17. I can still smell your cologne/perfume in my car. 

Weird and Funny Conversation Starters for Texting

How often do people LOL from a text anymore? A random funny text is the opportunity to connect over a shared sense of humor or maybe form some inside jokes that will have you and your best friend cracking up the next time you hang out. And when you want to stand out in someone’s phone inbox, a strange or random question can spice things up quickly.

  1. If your pet could talk, what would it say to you? 
  2. Could you send me your corniest joke? I’ll go first: Why do melons have weddings? … They cantaloupe.
  3. What’s the craziest advice you’ve ever received? 
  4. Have you seen the new movie, Constipated? (Wait for response) It hasn’t come out yet.
  5. When’s the last time you laughed so hard your stomach hurt? 
  6. What celebrity would play you in a movie about your life? 
  7. What’s your weirdest hidden talent? 
  8. What’s the worst prank someone has ever played on you?
  9. Are you a loan? Because you got all my interest🏦😜
  10. (Send a Step Brothers GIF) Our friendship in a nutshell.
  11. What’s the difference between a piano, a tuna, and a glue pot? (Wait for response) You can tuna piano, but you can’t piano a tuna. (They ask about the bond) …I knew you’d get stuck there 😉
  12. (Send a funny gasping GIF) My face when I found out ______. 
  13. Would you cut off your pinky toe for $1 million? 
  14. OMG, you won’t believe what just happened.
  15. Would you be on my team for the zombie apocalypse? 
  16. What’s the weirdest food combo you’ve ever tried?
  17. What food describes your personality? 
  18. Do you believe in aliens? What about ghosts? 
  19. What’s the funniest thing you’ve ever done in public? 
  20. Two strands of DNA are walking down the street. One says to the other: do these genes make me look fat?
  21. What would the color blue smell like? 

Deep Conversation Starters for Texting

Short and sweet don’t mean shallow. Some profound connections can be built up via text, making for even deeper relationships IRL. Once you’ve been texting someone for a while, don’t be afraid to get a little philosophical or personal with a conversation-starting question.  

  1. What is a controversial opinion you have?
  2. What is your proudest accomplishment?
  3. What is something that scares you but you’d like to do anyway?
  4. Who are you closest to in your life?
  5. What are your top three life goals?
  6. How have you changed since your teenage years?
  7. How important is family for you?
  8. If you could change one thing about yourself, what would you change and why?
  9. What’s the biggest lesson you’ve learned this year? 
  10. Where were you ten years ago, and where do you want to be ten years from now?
  11. What’s the most significant thing people misunderstand about you?
  12. What is a topic you could talk about for hours?
  13. How do you define success?
  14. What is your definition of true happiness?
  15. Do you believe in conspiracy theories? Which ones?
  16. At what age did you indeed “find yourself”? Are you still discovering who you are?

Key Takeaways: How to Have a Great Conversation Over Text

Compared to phone calls and in-person conversations, texting is a pretty low-stake form of communication. You can push some boundaries and take solace in the fact that it’s only a text message, after all. Why not set yourself apart from the millions of other texts and try something new? 

If you don’t know where to start, remember these tips for creating a sound text thread:  

  • Keep it short: People move fast today, and messages are no different. Texts are for short blurbs, not novels. Giant chunks of words can be hard on the eyes, so it’s best to keep your initial conversation starters to a few lines or less. When in doubt, a little mystery may warrant a better response. 
  • Ask questions: The art of regular conversation still applies via text. People love to talk about themselves, so they express interest in what they have to say by asking questions. 
  • Spark interest: Most people get asked, “how are you?” or, “what do you do for a living?” several times a day. You can generate a far more intriguing text conversation by bringing up unique topics, funny references, or unconventional subjects. 
  • Compliment them: Who doesn’t love a positive message on their phone? Whether you’re trying to flirt or initiate a conversation with a friend, typing a nice compliment is an easy way to brighten your day.    
  • Reference something they said: When in doubt, you can always bring up past conversations that you want to continue. For example, if you previously discussed travel and your friend mentioned that they’ve always wanted to visit Greece, you can reignite the topic via text and ask about their specific interest in that destination. It shows that you’ve been paying attention and want to learn more. 
  • Use emojis or GIFs: The most significant thing missing from texts is nonverbal communication like facial expressions. Emojis and GIFs help people understand when we’re being goofy, flirty, or profound. Plus, they can make texting more fun. Read about the top 45 Emojis You Should Know and Their (Hidden) Meanings

No matter how far technology progresses, the basics of human connection and the art of conversation remain the same. If you want to uplevel your communication skills over text and in-person, learn How to Have and Hold a Dazzling Conversation With Anyone.

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