How to Start a Texting Conversation: Opening Lines & Tips

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A complete guide on how to start and keep a text convo going
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Texting someone new can be tricky. Whether you’re texting a crush, friend, or someone you just met, getting that initial conversation started can be awkward. Luckily, you don't have to overthink things. We're here with plenty of tips to help you get a conversation going! We spoke with dating and relationship coach Suzanna Mathews to bring you the best texting advice, so keep reading to learn which conversation starters can help you break the ice.

How do you start a texting conversation?

Start a texting conversation by commenting on something you both have in common, sharing something interesting, or asking an open-ended question. Try saying something like, “Planning anything this weekend?” or “You won’t believe what just happened.”

Section 1 of 3:

The Best Text Starter Conversations

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  1. Whether you’re chatting with your crush, a long-distance friend, or a complete stranger, sending that initial text can be nerve-wracking. Thankfully, you can send some simple questions and clever remarks to get them interested and start the conversation . Here are some of our favorite ways to start a text conversation:
    • “What did you do today?”
    • “What’s your astrological sign?”
    • “Planning anything fun this weekend?”
    • “Tell me about one of your pet peeves.”
    • “Do you have any hidden talents?”
    • “What’s your favorite food?”
    • “Have you watched any good movies lately?”
    • “Which emoji best describes you?”
    • “I’ve been thinking about you.”
    • “What’s been the best part of your day so far?”
    • “If you could have a superpower, what would it be?”
    • “Hit me with your best joke.”
    • “Help me pick dinner: pasta or tacos?”
    • “Saw a cute dog that reminded me of you.”
    • “Who’s your biggest role model?”
    • “How have you been? I miss you!”
    • “I saw you got a new job. How are you liking it?”
    • “Pineapple on pizza: delicious or disgusting?”
    • “You watching the game tonight?”
    • “You’ll never guess what I dreamed about last night.”
    • “If your pet could talk, what would they say?”
    • “What are your top three goals in life?”
    • “What do you like to do for fun?”
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Section 2 of 3:

How to Start a Conversation Over Text

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  1. If you want to pull someone into a conversation, think of a hook that's going to make them want to know more. Just be sure you have a good story to follow it up, or the conversation might fizzle out once you come out with the reveal. Try getting the conversation started with something like: [1]
    • "Okay, you're going to laugh at me, but I have to tell you what I did..."
    • "The craziest thing just happened to me!"
    • "Well, my morning just took an interesting turn."
    • "Please tell me you heard about..."
  2. Everybody loves a well-timed compliment , so if there's something you really like about the other person, let them know! But as Mathews advises, don't go overboard—laying it on too thick can actually backfire and make the other person feel like you're being insincere. [2]
    • Keep it simple and sweet by saying something like, "I really enjoyed meeting you!"
    • You could also say something like, "You seem really cool. We should hang out again soon!"
    • Or, you could make it more specific by saying something like, "You have an awesome sense of humor. I'm still laughing at your joke about the turtle!"
  3. If you know the other person is especially good at something, ask them for advice to get a conversation going. Not only will they be flattered, but there's some evidence that it will make them think more highly of you, too. [3] Then, use that as a lead-in to chat more about the situation you're asking about.
    • For instance, if you noticed that the person you're talking to is a really sharp dresser, you might send them a picture of two shirts and say, "Which one do you think I should wear to my interview?"
    • If their profile says they love to cook, you could say, "I'm having friends over to grill tomorrow. Do you have any awesome tips for cooking steak?"
  4. Think back to a previous conversation or look at their profile. If you were talking in person, it would feel really natural to start chatting about things you have in common. That makes it a perfect lead-in when texting because it follows the natural flow of conversation. And if it's something you talked about before, it will show that you were paying attention to them the last time you were together. [4]
    • If their profile has a picture of them with their dog, you could say something like, "What's your dog's name? I have a lab named Max!"
    • You might also say something along the lines of, "I remember you said you were into skiing. I'm going with some friends this weekend. Do you have any tips?"
  5. Asking questions is a great way to get to know someone, but try to avoid questions that can simply be answered with "yes" or "no." Instead, phrase your question in a way that invites the other person to explain more so they'll be more likely to open up to you and chat with you longer. [5]
    • Instead of saying, "Do you like pizza?" you might say, "What's your favorite pizza topping?"
    • Or, instead of saying, "Did you have a good day at work?" you could say, "What's your favorite thing about your job?"
    • Similarly, try to answer questions with a full sentence instead of just a one-word answer. [6]
  6. According to Mathews, memes, GIFs, and emojis are all great ways to communicate what you're thinking. [7] Even better, you don't have to rack your brain for something to say. If you see something posted on social media that you think the other person would think is funny, save it and send it to them, then see if you can build on their response to keep the chat going. [8]
    • For instance, if you're tired after a long day, you might send a GIF of someone collapsing on the floor. If you just want to say hi, you might send a clip of someone waving.
  7. As you get to know the person better, keep an eye out for news articles, videos, or press releases that they might think are cool. If you see something, text it to them with a little note, like "Have you seen this?" or "This made me think of you." [9]
    • If you like the same type of music, for instance, you might share a blog post where your favorite band announced a new tour.
  8. Jump right to chatting with them in person if you’re excited to see them again. Asking them to meet up IRL is an excellent start to a conversation, especially with a crush or partner. Plus, this also shows that you’re thinking of them.
    • Try sending them a message saying, “So, when’s our next date?” or “Hey, want to check out that new restaurant downtown this weekend?”
  9. A quick check in can do wonders when it comes to starting a text conversation. Think of it as seeing someone in person and saying, “Hey! How are you?” This open-ended question lets them steer the conversation, giving them the opportunity to talk about whatever they’d like.
    • Start by texting them, “Thinking about you! How are things?” or “Hey! What’s up?”
    • Then, continue the conversation based on what they say next. For instance, if they’re not feeling great, ask them what’s the matter; if they’re heading to a movie, ask what movie they’re seeing.
  10. You definitely don't want to spend time thinking of the perfect opening line only to get back an awkward, "Um, who is this?" It might not be the most creative lead-in, but it gives them a chance to save your number if they haven't already. Also, try not to wait too long to text them after you get their number so you'll be fresh in their memory. [10]
    • For instance, you might say, "Hey, this is Leah from the gym earlier!"
    • Or, you could say, "Hi Jim, this is Chris from work!"
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Section 3 of 3:

How to Keep a Text Conversation Going

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  1. Try to avoid hopping around from one topic to another. If you start chatting about something, let the conversation naturally flow in that direction for a little while. If you abruptly start talking about something else, it might feel like you're not really paying attention to what the other person is saying. If it feels like things are stalling out, though, it's fine to move on to something else. [11]
    • If the person is talking about their day at work, ask a follow-up question or share something about what you did that day.
  2. Don't take yourself too seriously. As Mathews suggests, try to stay positive, clever, and funny when you're texting. [12] Everything doesn't have to be a joke, but if your attitude is generally upbeat, you'll be more likely to keep the other person engaged in what you're talking about. [13]
    • Try to avoid sarcasm—it doesn't usually translate well through text. In addition, avoid sensitive subjects like politics, religion, illness, sex, or finances. It's better to wait until you know someone better to talk about that stuff, and it's better to discuss them in person, anyway.
  3. Just because they always have their phone on them doesn't mean they have to (or can) respond to texts at all hours. If you notice that they're mostly sending one-word answers to your questions or if there are long gaps between texts, they might be busy. The best thing you can do is to busy yourself with something else for a while. [14]
    • If they always respond to your texts with short answers, they might not be interested in texting you. That doesn't necessarily mean they don't like you, though—some people just don't like to text, and that's okay!
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Sample Questions to Ask over Text

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  • Question
    How do you talk to a beautiful woman?
    Suzanna Mathews
    Dating & Relationship Coach
    Suzanna Mathews is a Dating and Relationship Coach and the Founder of The Date Maven. With over a decade of experience, she specializes in creating mindset tools, social strategies, and digital strategies that help her clients elevate dating and deepen connections. Suzanna holds a BA in Communications from Bethel College, North Newton, and an MA in Theater and Dramatic Arts from Wichita State University.
    Suzanna Mathews
    Dating & Relationship Coach
    Expert Answer
    Guys often want to lead with things like you're beautiful, you're gorgeous, you're pretty and any beautiful woman has probably heard that 20 times already before lunchtime. Don't be the guy that is the 21st person to tell her that she's attractive, be the guy who noticed that something just a little bit different about her and just doesn't become another cliché of, you know, yet another guy who hit on such a predictable way.
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      Tips

      • Emojis can be a fun way to spice up your texts, but don't go overboard—especially if you're texting someone you work with or a professional contact.
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      References

      1. ↑ https://rendezvousmag.com/how-to-start-a-conversation-over-text/
      2. ↑ Suzanna Mathews. Dating & Relationship Coach. Expert Interview. 18 August 2021.
      3. ↑ https://www.scientificamerican.com/article/asking-advice-makes-a-good-impression/
      4. ↑ https://www.thelist.com/53749/the-right-way-wrong-way-text-crush/
      5. ↑ https://www.nbcnews.com/better/lifestyle/how-have-better-conversations-people-you-ve-just-met-according-ncna1005941
      6. ↑ https://www.chicagotribune.com/lifestyles/sc-fam-0512-conversation-101-20150515-story.html
      7. ↑ Suzanna Mathews. Dating & Relationship Coach. Expert Interview. 18 August 2021.
      8. ↑ https://rendezvousmag.com/how-to-start-a-conversation-over-text/
      9. ↑ https://www.thelist.com/53749/the-right-way-wrong-way-text-crush/
      1. ↑ https://lifehacker.com/the-dos-and-don-ts-of-texting-a-romantic-interest-1753671407
      2. ↑ https://www.chicagotribune.com/lifestyles/sc-fam-0512-conversation-101-20150515-story.html
      3. ↑ Suzanna Mathews. Dating & Relationship Coach. Expert Interview. 18 August 2021.
      4. ↑ https://www.thelist.com/53749/the-right-way-wrong-way-text-crush/
      5. ↑ https://rendezvousmag.com/how-to-start-a-conversation-over-text/

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