Good Conversation Starters & Prompts for Text Messaging

Nervous about sending the first message? Break the ice and spark deeper chats with our text conversation starters.

Original prompts for good text message conversation min

Need help getting that text conversation started? You’re not alone.

In today’s world, it’s not uncommon to start conversations in DMs on social media and then move to text messaging or other chat platforms. 

Whether you’re online dating or a friendly conversation turned into a professional opportunity, there are tons of scenarios where it’s on you to start the conversation, and we could all use a hand in making the best first impression. 

The guide below will take you through the do’s and don’ts of opening a chat and plenty of good conversation starters for texting, so you can stop the never-ending staring contest with your phone.


The Do’s and Don’ts of Starting Text Message Conversations

Although we’ve covered text message etiquette in a previous blog, there’s an added layer of complexity when starting a new chat with someone. 

To make sure it’s an interesting and, most importantly, welcomed conversation, follow these six simple rules:


  1. If the person doesn’t have your number or they don’t know who you are, start off by introducing yourself. This will avoid any confusion and prevent the inevitable “Sorry, who’s this?” message, so you can get right into the conversation.
  2. If you recently saw them at a get-together, outing, or special event, bring it up in your message. 
    • For example, “Hey Lily! It’s Brandon. It was great meeting you at the concert last night! What’d you think of the show?” 
    • If you took pictures together when you hung out, you already have the perfect text conversation starter! Sharing the photos with a fun message like “Name a better duo” or “Damn, we look good!” is a great way to break the ice.
  3. Especially if it’s a professional introduction, re-read your message before you hit send. Even a small typo can completely change the meaning of a sentence, so it’s always better to be safe than sorry. You only get one chance to make a first impression, after all!



  1. Don’t ask simple questions that can be answered with a quick “yes” or “no.” Stick to open-ended questions as often as possible to get the conversation flowing. This strategy is a great way to keep the other person engaged and take your discussions deeper.
  2. Unless your text conversation starter is for a professional opportunity and requires a lengthy introduction, don’t make your first message long. If their first text from you is a short story, it can be overwhelming and may push them away.
  3. If they don’t get back to you right away, don’t text again. It can be tempting to reach out again after a little while—especially if you’re eager to hear back from them—but it’s best to give them time and avoid blowing up their inbox with multiple messages. If and when they want to get back to you, they will.
  4. Never complain, and never explain.  Don’t allow yourself to go down the dreaded “venting” path. While it can be cathartic to get a stressful day off your chest, or share a pet peeve, it’s better to keep things positive as you get to know each other better and avoid creating a cycle of negativity. Don’t look for things to go wrong, either.  Don’t assume you need to apologize, or take the edge off with an LOL. Allow your words to stand on their own while someone else replies. Assume they will interpret your information positively and share an explanation, rather than an apology, if your response isn’t well received. 


Flirty Text Message Conversation Starters 

Now that we’ve gone through the do’s and don’ts of text conversation starters, let’s get into some fun ways to strike up a chat with someone you’re interested in.

The MOST common roadblock for people pursuing a new partner is starting a meaningful conversation without coming across as awkward or embarrassing themselves.

But we’re often our own worst enemies in these situations. We’ve all spent five to ten minutes overthinking what to say and typing and retyping the same message twenty times…

But at the end of the day—although it might sound cliché—keeping it light and being yourself is the best way to start a flirty chat with your crush.   

The next time the opportunity arises, try out these flirty text message conversation starters, and feel free to add your own spin to them if the inspiration strikes!

If you’re already having a friendly chat, add one of these questions into the mix to make things interesting:

  • What does your ideal first date look like?
  • What do you look for the most in a guy/girl?
  • What’s your type?
  • Do you have a celebrity crush? If so, who is it?

If you saw each other recently, you could say:  Hey Eric, I’m glad we ran into each other the other night! Hanging out with you was honestly the highlight of my night :)

If you’ve met your crush before, but it’s been a while since your last hangout, you could text something like:  It’s been too long since we’ve seen each other. We should change that ;)

If a friend gave you their number, the direct route is always a great option:  Alright, I’ll be honest ๐Ÿ˜‡ I asked Leo for your number because I wanted to ask you out. Would you want to grab coffee sometime?

Or, if you’ve never met and you’re chatting through social media, try sending a DM in response to a recent post or story of theirs:

  • I like (band or DJ) too, you’ve got great taste ;) What’s your favorite album?
  • You like (band, DJ, movie)? Wow, so you’re hot and you have great taste.

And if you want to have some fun, you could always get a little cheesy with it and send a silly pickup line, like:  Are you taking boyfriend/girlfriend applications? I think I’d be a tremendous asset to your team.

But as a general rule, keep these to a minimum—especially if you’re not too familiar with the person. Many pickup lines fall flat or can come across as weird or creepy!

Humor goes a long way in warming up the room, so get a set of fun memes to send based on the conversation.   Text messages often feature a GIF search right in the chat, and if a picture is worth a thousand words a GIF is worth a million.  Consider sending a YouTube video or music track as a response rather than a standard text message and to evoke an emotional response that only music can. 


Text Message Conversation Starters for Couples

Whether you’re dating exclusively or married with years of bliss under your belt, it’s important to have interesting and meaningful conversations with your partner.

Give these text conversation starters a try next time you want to connect with your sweetheart:

  • Hey love, what’s your favorite thing about our relationship? I know what mine is, but you go first!
  • I can’t stop thinking about our trip last summer. If we could go anywhere together, where would you want to go?
  • What’s the most impactful way our relationship has helped you grow as a person? *You can share yours before asking this question or after they respond with theirs.
  • If we could start any hobby together, what would you want it to be?


Deep Text Message Conversation Starters

If you want to mimic those late-night chats on the couch or in bed that keep you up for hours, drop some of these questions in your text thread:

  • What’s your biggest regret and why?
  • Do you feel fulfilled at work? 
  • If you could have any career, what would it be?
  • If you could go back and change one thing about your life, what would it be?
  • What’s your favorite thing about life?
  • Do you have a life motto? If so, what is it?
  • If you won the lottery, what would you do with the money?
  • Is there a song or movie that changed your life? If so, what is it?
  • What does happiness mean to you?
  • What would be your perfect day?
  • What are you most proud of about yourself?
  • Who do you look up to most in life and why?


Funny Text Message Conversation Starters

Getting a bit silly with a new friend or romantic interest is a great way to bring you closer, learn their sense of humor, and, of course, make each other laugh.

Next time you can’t think of something funny, use this list of text conversation starters as inspiration:

  • Tell a funny story from your life or an experience you two shared in the past.
  • What’s your spirit animal, and why?
  • What’s the craziest thing that’s happened on a first date?
  • What’s your best drinking story?
  • What’s the weirdest thing you’ve ever eaten?
  • What’s an embarrassing story from your childhood?
  • What’s your favorite comedy movie or TV show?
  • How long would you survive in the zombie apocalypse?


The Takeaway

As helpful as these ice-breakers can be in a pinch, the most fun and engaging conversations involve topics you’re both passionate about.

So, when using the above suggestions as a reference, feel free to make them your own. Ask questions that you’re genuinely interested in, flirt in your own unique way, and keep the conversation going with open-ended questions to learn more about them and get closer with each other.

Above all, keep it light-hearted, don’t be afraid to get deep, and have fun!

Happy texting!

And, if your texting turns into an epic story: whether it’s a drama, romance, or comedy, you can turn your chat and text message histories into a texting book from Keepster.  These are the perfect way to combine messages and photos to create the ultimate story about how your conversations got started in the first place and memorialize your exceptional conversational skills in a hardbound book.  Learn more about Keepster texting books


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