How to Start and Keep a Text Conversation Going

Co-authored by Imad Jbara and Aly Rusciano

Last Updated: March 7, 2023 References

You just got someone’s number, but now you’re staring at your phone, wondering what exactly you should text them. We’ve all been there, but fear not! In this article, we’ll share with you the best ways to start a text conversation and keep it going. With our simple tips and tricks, you’ll be texting like a pro in no time!

Things You Should Know

Get a conversation started by asking open-ended questions that require more than a “yes” or “no” answer.
Find common interests to talk about to keep a text conversation interesting and fun.
Avoid sending too many texts at once if they don’t respond—they’re probably just a bit busy!

Method 1

Method 1 of 3:

Opening the Conversation

1
Start the conversation by telling them who you are. If you know this person doesn’t have your number, let them know it’s you. Although a bit of mystery can build interest, keeping your identity a secret for too long could be a little creepy. Stick to stating your name or asking if they know who it is.
- “Guess who this is?”
- “Hey you! It’s Luis. Liam said you wanted my number?”
- “Hi Isabella! It’s Sierra, and you won't believe what happened after chemistry!”
2
Text them about something you recently did together. If you’ve hung out with this person before, make your initial text about the last thing you did together in person. Using an event as a reference point is a great way to spark a discussion and reminisce together.
- “Whoa, I’m so full. That restaurant was so good!”
- “Wow, Ms. Thornberry’s class was so boring today. I was falling asleep 😴”
- “I can’t stop thinking about the concert! I wish we had a time machine so we could relive it all over again.”
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3
Ask them an open-ended question to get a conversation going. Asking a question that requires more than a “yes” or “no” response is a great way to start a meaningful discussion. Consider asking them about their day or even their opinion on something. And when they respond, follow your curiosity and ask even more questions, sharing your own insight as well.^{[1]
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Expert Source

Imad Jbara
Dating Coach
Expert Interview. 5 November 2019.}
- “What are your plans for the weekend?”
- “What kind of shoes were you wearing today? I totally want to pick up a pair!”
- “How was the pep rally today? I hate that I had to miss it!”
4
Share a silly story to grab their attention. Adding humor to your first text is a great way to get the ball rolling. Plus, it beats the usual “Hi!” or “What’s up?” Try texting them something unique about your day. If they’re interested in what you’re saying, they’ll likely text you back.
- “So, I just walked 20 blocks for a sandwich only to realize that today’s Sunday and the store is closed. How’s your day going?”
- “Well, I totally didn’t just read the wrong chapter for the reading assignment 🙃”
- “Dave just slipped on a banana peel. No joke. It was like something straight out of a cartoon! Never thought those warnings from Bugs Bunny were legit.”
5
Use emojis to convey emotions. Emojis are super fun and useful because they can help you share exactly what you’re feeling. For instance, sarcasm can often get lost in texts, but emojis like 🙃 and 🙄 can help clarify a sarcastic tone. Try sprinkling an emoji or two after your message or when responding to a text.^{[2]
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- “Chemistry was really interesting today :)”
- “I just love doing taxes 🙃”
- “Are you watching the finale? The suspense is killing me 😩”

Method 2

Method 2 of 3:

Keeping the Conversation Going

1
Keep asking questions to learn more about them. Continuing to ask questions throughout a text conversation can keep you both engaged. Ask them about what they’ve told you so far, just as you would in an in-person conversation. The more questions you ask, the more likely you’ll keep chatting.^{[3]
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Expert Source

Imad Jbara
Dating Coach
Expert Interview. 5 November 2019.}
- “What’s your favorite food?”
- “That sounds like a fun weekend! What movie did you guys see?”
- “I’m so jealous you went to Disney World! You better take me with you next time 😉 What was your favorite ride?”
2
Send them pictures to help them feel included. Pictures are a great way to give someone insight into what you’re doing, especially when they’re not by your side! Try snapping a pic of what you’re cooking while chatting with them or something neat you saw on your evening walk. This way, they’ll feel like they’re involved in your life even if they’re miles away.
- If you don’t have any pictures to share, try sending them a GIF or meme to relay your emotions, an activity, or something funny.
3
Find common interests to discuss. After you’ve asked a series of questions, you’re bound to know more about who you’re texting. Notice if they like any of the things you like. Bringing up common interests is an excellent way to keep a conversation going and build a relationship.^{[4]
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- “No way! I’m a huge Yankees fan too! What’d you think of last night’s game?”
- “I’m obsessed with Olivia Rodrigo! She takes me back to my angsty teen years 😅”
- “How have you never told me you love to bake? So do I! What’s your favorite recipe?”
4
Play a texting game to pass the time. If you run out of questions to ask or things to say, try playing a casual texting game to continue the conversation. Games like Would You Rather, 2 Truths and a Lie, and 21 Questions translate extremely well through text. Plus, if you’re texting a crush or significant other, you can always add a flirtatious flair to the game.^{[5]
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- If you’re texting a partner, play Would You Rather (Flirty Edition): “Would you rather never be able to hug or make out with me again?”
- If you’re texting a friend or crush, play 2 Truths and a Lie: “I’ve never been on a boat, my favorite color is pink, and I’ve ridden an elephant.”

Method 3

Method 3 of 3:

Texting Tips and Tricks

1
Send texts that are appropriate for your relationship. The texts you send your mom, best friend, colleague, and partner are going to be very different from each other. Consider the relationship you have with the other person, and avoid too personal straight away, especially if you don’t know them that well.^{[6]
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- If you’re texting a family member, you probably don’t want to use the same flirtatious language you’d use with your significant other.
- If you’re texting someone you don’t know well, keep things casual and mellow to start. Then, as the conversation continues, consider their tone. Mirroring their texting style can even help you connect and build a stronger relationship.^{[7]
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2
Take your time responding and sending texts. It may seem counterintuitive, but taking a few seconds or minutes to type out your response may help build interest. Texting too frequently can also overwhelm the other texter, especially if you send them back-to-back messages. Opt for sending one consecutive message at a time that’s well-thought-out.
- Think of texting like any in-person conversation. There are generally pauses between discussion points for each party to share their points—the same goes for texting! If you text too many short messages at once, the other person may feel interrupted.
- If they don’t text you back right away, don’t sweat it! They may be busy, so be patient and wait for their response instead of sending multiple messages.
3
Keep the conversation lighthearted. Long detailed conversations are best left for phone calls or in-person chats. Sometimes, there can be miscommunications while texting, so it’s better to leave serious topics out of your texts. Instead, focus on fun and simple topics that encourage back-and-forth conversations, especially if you’re not specifically close to this person.^{[8]
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- If there’s something more serious you’d like to discuss, like politics or the future of your relationship, text the person asking if they can meet or are available to chat.
- For example, you might text something like, “Hey! Can I call you? There’s something I want to talk about, and it’s too much to type up,” or “What are you doing tomorrow? There’s something I’ve been meaning to ask you, and I would love to meet for coffee.”

Fun Conversation Starters

Expert Q&A
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Question

How do you start a good text conversation?

Imad Jbara
Communication Coach
Imad Jbara is a Dating Coach for NYC Wingwoman LLC, a relationship coaching service based in New York City. 'NYC Wingwoman' offers matchmaking, wingwoman services, 1-on-1 Coaching, and intensive weekend bootcamps. Imad services 100+ clients, men and women, to improve their dating lives through authentic communication skills. He has a BA in Psychology from the University of Massachusetts Dartmouth.

Imad Jbara

Communication Coach

Expert Answer

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You could ask question, share an interesting observation, or try flirting with them. Honestly, it can be kind of hard to get a great conversation going over text. You just miss out on a lot of the magic and spontaneity when you're texting and it's easy to misread tone when you can't hear someone speak. If you're really looking for a meaningful conversation, try calling them or talking in person!
Question

What is a good text conversation starter?

Imad Jbara
Communication Coach
Imad Jbara is a Dating Coach for NYC Wingwoman LLC, a relationship coaching service based in New York City. 'NYC Wingwoman' offers matchmaking, wingwoman services, 1-on-1 Coaching, and intensive weekend bootcamps. Imad services 100+ clients, men and women, to improve their dating lives through authentic communication skills. He has a BA in Psychology from the University of Massachusetts Dartmouth.

Imad Jbara

Communication Coach

Expert Answer

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The easiest way to get a text chat started is to ask the person a question. This way they know how to easily reply to you. Stick to an easy, open-ended question so they don't have to think about their answer too much.
Question

If there is miscommunication during a text conversation, how do you resolve it without typing a whole paragraph?

wikiHow Staff Editor
Staff Answer
This answer was written by one of our trained team of researchers who validated it for accuracy and comprehensiveness.

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Try asking if you can meet up in person to talk or chat on the phone. Sometimes it's easier to vocalize your concerns or misinterpretations rather than typing them out.