How to Keep a Text Conversation Going with a Boy

Written by John Keegan | Edited by Hunter Rising

Last Updated: February 10, 2023 References

Texting a guy you’re crushing on is such a great way to get to know him. Even though it’s completely normal for conversations to slow down or fizzle out, there are still a lot of ways you can catch his attention. We’ll go over a ton of helpful ways to revive and carry a conversation along with some example messages you can try out to keep him interested!

This article is based on an interview with our professional dating coach, John Keegan, founder of The Awakened Lifestyle. Check out the full interview here.

1

Ask him open-ended questions.

Use questions that start with “what” or “how” to get him talking. Open-ended questions require more than a one-word answer, so it gives the guy a chance to go into more details. Try asking him about his life, the things he likes, or just fun hypothetical questions to get the ball rolling. Just try to stay away from taboo topics, like politics or religion, since they could lead to a heated discussion.^{[1]
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John Keegan
Dating Coach
Expert Interview. 19 August 2021.} Some fun questions you can try asking include:^{[2]
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- “What did you think of that movie last night?”
- “If you won the lottery, how would you spend the money?”
- “What’s the best advice someone’s ever given you? 🤔”

2

Mention something from an old conversation.

Use this easy in so you don’t have to think of a new topic. If you’ve already been chatting with your guy, look back through your old messages to find something you’ve already mentioned. Since you’ve already brought it up before, it’ll be pretty easy for you and him to pick up right where you left off.^{[3]
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Julia McCurley
Certified Professional Matchmaker
Expert Interview. 30 September 2021.} You could try saying something like:^{[4]
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- “I tried that new coffee shop we talked about yesterday and it was so cozy 🙂 We should definitely go sometime!”
- “Remember that video I mentioned last night? Well I FINALLY found it and it’s so embarrassing.”
- “You said something about getting a new game this week. Did you get a chance to play it yet?”

3

Comment on something he shared.

He’ll love that you remembered and paid attention to him. Take a peek at the guy’s social media to see if he’s posted anything recently. You could also bring up something that he told you to check out earlier in your conversation. Since he took the time to send it or post it, he’ll appreciate that you noticed and want to keep chatting. A few things you might say are:^{[5]
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Expert Source

John Keegan
Dating Coach
Expert Interview. 19 August 2021.}
- “I just checked out that song you sent and it’s SO good! Where did you find it?”
- “Wow, I love that picture you posted on Insta! You look really good 😍”
- “OMG that video was so funny! How did you even get the idea for that??”

4

Talk about his interests.

Guys love to gush about the things they’re into right now. You probably have some idea of what the guy likes, but scroll through his social media if you aren’t sure so you can see what he posts about. Even if you aren’t as interested in the subject, he’ll have a lot to talk about and he’ll really love that you cared enough to ask about it.^{[6]
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Julia McCurley
Certified Professional Matchmaker
Expert Interview. 30 September 2021.} Try saying something like:^{[7]
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- “I’m a huge movie nerd too 🤓 What’s your favorite thing that’s come out this year?”
- “I’ve been trying to get into video games too. Which ones would you recommend playing first?”
- “It’s so cool that you make music! How did you get started doing that?”

5

Ask about his day.

Catch up with him so you get in the habit of chatting daily. Since you're both probably a little busy throughout the day, this is a great way to start up a conversation that died out earlier. Even a quick message as he wraps up his day could bring a smile to his face and keep your conversation alive. Reach out and message him questions like:^{[8]
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Expert Source

John Keegan
Dating Coach
Expert Interview. 19 August 2021.}
- “Hey you 🙂 what have you been up to?”
- “Man, it’s been a crazy day for me. What about you?”
- “You had a math test today right? How did that go?”

6

Give him a compliment.

Saying something nice boosts his ego and shows you care. Guys love hearing nice things about themselves, so take a second to tell him! You could respond to something else he said or start a new conversation.^{[9]
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Julia McCurley
Certified Professional Matchmaker
Expert Interview. 30 September 2021.} Just compliment him about how he looks or what you admire about him to show him that you noticed. Some nice things to say to your guy might be:^{[10]
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- “Has anyone ever told you that you have the cutest smile ever??”
- “That shirt you wore today really made your eyes pop! 😍😍😍”
- “Thank you SO much! That was really helpful advice. You always know exactly what to say.”

7

Share a fun story.

Relatable stories from your life help him get to know you even better. Rather than making the guy do all the talking, open up a little so the guy has a chance to learn more about you too. If the topic you’re talking about reminds you of something that happened to you, bring it up if you’re comfortable sharing it. Some ways you can start a story are:^{[11]
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Expert Source

John Keegan
Dating Coach
Expert Interview. 19 August 2021.}
- “OMG that reminds me of this time I got SO embarrassed at work! 😅”
- “Back when I was younger, I used to LOVE exploring until I got lost.”
- “Did your family ever go on big vacations? This one time, we went to Disney World and it was soooo fun!”

8

End your message with a cliffhanger.

Keep him guessing what happens next so he has to message back. Instead of sending all the details in a single message, send him a few vague details to pique his interest. He’ll really want to find out what you’re talking about, so he’ll message you back asking for more. Some fun things to say may include:^{[12]
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- “I had a dream about you last night. Can you guess what it was about?”
- “OMG! You’ll never believe what happened in science class today…”
- “I can’t wait to tell you about my trip! It got pretty crazy one night 😏”

9

Tell him when he’s on your mind.

He’ll feel really special knowing that you’re thinking about him. There are a lot of things you could see throughout the day that remind you of the guy, so be sure to mention them to him. Even if you’re just wondering how he’s doing, reach out and let him know.^{[13]
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Julia McCurley
Certified Professional Matchmaker
Expert Interview. 30 September 2021.} Some things you can try messaging could be:^{[14]
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- “Hi! You’ve been on my mind a lot today 🥰 How are you doing?”
- “I just watched a movie, and all I could think about the whole time is how much you would have loved it.”
- “I just had some Thai food and it reminded me of that really nice time we had at that one restaurant together.”

10

Send him pictures or videos.

Show him what you’re up to so he misses you more. You could send him a cute selfie, a pic of where you are, or even a funny meme you found online. Just be sure not to send him anything too sexual without building up to it first, or else it could make him feel uncomfortable. You might say something like:^{[15]
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- “Check out this sunset that I just saw!! Isn’t it so beautiful?”
- “Not sure if I like this new outfit yet. What do you think?”
- “I saw this meme and couldn’t stop laughing 🤣 I just had to share!”

11

Tease him.

Some playful jabs let him know you like him more than a friend. As you get to know the guy a bit better, you’ll feel a little more comfortable poking fun at him a little bit. Just pay attention to how he responds so you aren’t bullying him or hurting his feelings. As long as you aren’t being mean, he’ll have a fun and flirty time with it. Some small things you can say to tease him are:^{[16]
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- “You really think you can beat my high score?? I’d like to see you try 😉”
- “Oh, you had a ‘fum’ night? Don’t worry, I had a lot of fum too 😜”
- “You’ve never seen Star Wars!? Were you born under a rock??? Haha”

12

Flirt with him.

Be upfront that you’re interested so he doesn’t get confused. If you’re starting to feel closer to the guy or want to make your feelings clear, try shooting your shot! Throw a few emojis into your messages to keep them light and fun. Some cute and fun things to say to him are:^{[17]
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Expert Source

John Keegan
Dating Coach
Expert Interview. 19 August 2021.}
- “Texting you is fun, but I think we’d have more fun in person 😏”
- “The only thing that would make this movie better is you cuddled up next to me.”
- “Do you want to know what I’d do if we were together? Use your imagination 😘”

13

Make a plan to meet in person.

Try to get together so you can build your physical connection with him. Even though texting is a great way to learn more about a guy, hanging out together is better for finding out if you’re a good match. Clearly let your guy know that you want to see him so he gets excited about spending time with you. Some ways you can ask to meet up could be:^{[18]
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- “So there’s a concert this Saturday night and it’s really close by. Would you want to come with me?”
- “I’d love to see you again soon! ☺️ When are you free this week to meet up?”
- “Guess who got tickets to the baseball game next Friday!! Do you wanna be my plus one?”

14

Give him some time and space.

Texting too much or oversharing could seem needy. If you’ve barely talked to the guy and you’re already telling him how much you like him, it might turn him off. Rather than messaging him all the time about what you’re feeling, take some breaks and keep some of your feelings to yourself. You can always talk more when you hang out in person.^{[19]
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Expert Source

John Keegan
Dating Coach
Expert Interview. 19 August 2021.}

15

Let the conversation end naturally.

It’s okay for conversations to eventually fizzle out. If the guy you’re talking to doesn’t respond or only replies with short messages, he might be signaling that he wants to end the conversation. If he doesn’t end up responding at all, give it a little time before messaging him about a new topic.^{[20]
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- Letting a conversation end doesn’t mean the guy isn’t interested in you. It might just be a sign that he's busy or want to talk about something else.

Example Questions to Ask over Text

Sample Questions to Ask over Text

Warnings

Only send appropriate pictures since unsolicited sexual images could make the other person feel uncomfortable.^{[23]
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