How To Keep A Text Conversation Going With A Boy - WikiHow

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15 Ideas to Maintain a Flirty & Sweet Text Convo With a Boy Download Article The top ways to continue a text conversation with a guy Explore this Article IN THIS ARTICLE 1 Ask him open-ended questions. 2 Mention something from an old conversation. 3 Comment on something he shared. 4 Talk about his interests. 5 Ask about his day. 6 Give him a compliment. 7 Share a fun story. 8 End your message with a cliffhanger. 9 Tell him when he’s on your mind. 10 Send him pictures or videos. 11 Tease him. 12 Flirt with him. 13 Make a plan to meet in person. 14 Give him some time and space. 15 Let the conversation end naturally. Example Questions to Ask over Text + Show 13 more... - Show less... Other Sections Tips and Warnings Related Articles References Written by John Keegan | Edited by Hannah Dillon

Last Updated: December 2, 2024 Fact Checked

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This article was written by John Keegan and by wikiHow staff writer, Hannah Dillon. John Keegan is a Dating Coach and motivational speaker based in New York City. With over 10 years of professional experience, he runs The Awakened Lifestyle, where he uses his expertise in dating, attraction, and social dynamics to help people find love. He teaches and holds dating workshops internationally, from Los Angeles to London and from Rio de Janeiro to Prague. His work has been featured in the New York Times, Humans of New York, and Men's Health. There are 9 references cited in this article, which can be found at the bottom of the page. This article has been fact-checked, ensuring the accuracy of any cited facts and confirming the authority of its sources. This article has been viewed 250,249 times.

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. With the help of expert dating coaches John Keegan and Julia McCurley, 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!

Having a Text Conversation with a Boy

• Ask him questions about himself.
• Ask him about his plans based on any interests or activities he enjoys.
• Give him a sincere compliment.
• Bring up something from pop culture to chat about.
• Make a joke or share a funny meme.

Steps

1

Ask him open-ended questions.

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1. 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. Keegan says to try and stay away from taboo topics, like politics or religion, since they could lead to a heated discussion.[1] Some fun questions you can try asking include:
   • “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? 🤔”
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2

Mention something from an old conversation.

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1. 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. According to Keegan, 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.[2] You could try saying something like:[3]
   • “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.

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1. 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. Keegan suggest that a few things you might say are:[4]
   • “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??”
   • Reader Poll: We asked 356 wikiHow readers who've talked to their crush online, and 56% of them agreed that the best way to get his attention is by responding to his story with an emoji or quick reaction. [Take Poll] Then, you can follow up with a conversation!
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4

Talk about his interests.

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1. 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. Keegan says that 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.[5] Try saying something like:
   • “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.

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1. 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. Keegan suggests to reach out and message him questions like:[6]
   • “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?”
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6

Give him a compliment.

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1. Saying something nice boosts his ego and shows you care. Guys love hearing nice things about themselves, so take a second to tell him! Keegan says you could respond to something else he said or start a new conversation.[7] 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:[8]
   • “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.”
   EXPERT TIP

   Julia McCurley

   Certified Professional Matchmaker Julia McCurley is a Certified Professional Matchmaker, Relationship Coach, and the CEO of Something More, Austin's premier matchmaking service. She has been creating happy couples in Austin for over 12 years and has helped hundreds of singles on their journey to finding love. Her blogs have been published on the Huffington Post, Good Men Project, SheKnows, Emlovz, and The Dating Truth. She also just published her first book, Game Set Match: A Professional Matchmaker's Advice on How to Win At the Game Of Love. Julia holds a BA in Business and Communications from The University of Puget Sound and received her Master Executive Matchmaker Certification from The Matchmaking Institute. Julia McCurley Certified Professional Matchmaker

   Complimenting your guy is a great way to renew your spark. Try saying something like "You have such a great sense of humor! I miss your jokes." This moves the conversation in a direction that prompts him to suggest that you meet up soon sometime.

7

Share a fun story.

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1. 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. According to Keegan, some ways you can start a story are:[9]
   • “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!”
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8

End your message with a cliffhanger.

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1. 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:[10]
   • “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.

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1. 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. Keegan says that even if you’re just wondering how he’s doing, reach out and let him know.[11] Some things you can try messaging could be:[12]
   • “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.”
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10

Send him pictures or videos.

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1. 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:[13]
   • “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.

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1. 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:[14]
   • “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”
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12

Flirt with him.

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1. 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. Keegan says that some cute and fun things to say to him are:[15]
   • “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.

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1. 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:
   • “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?”
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14

Give him some time and space.

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1. 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. According to Keegan, you can always talk more when you hang out in person.[16] EXPERT TIP

   Kristina Mirgorodskaya

   Dating Expert Kristina Mirgorodskaya is a Dating Coach and the Marketing Director of Amiccio, a New York City social app that helps singles make new connections. Amiccio connects singles by hosting parties, socials, beginners salsa, bachata, and tango classes, and speed dating events. With over four years of experience, Kristina specializes in leveraging people skills, cultivating welcoming environments, and intercultural communication. Her expertise allows her to easily bring people together. Kristina earned a degree in business from Baruch College. Kristina Mirgorodskaya Dating Expert

   Give your crush some space if he doesn't reply after two texts. If you keep sending messages, you'll come off as desperate—or it could annoy him so much that he won't respond at all. He could be busy or just not in the mood to talk right now. Give him time to reply before shooting off another text.

15

Let the conversation end naturally.

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1. 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.[17]
   • 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 wants to talk about something else.
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Example Questions to Ask over Text

Sample Questions to Ask over Text

Expert Q&A

Search Add New Question Ask a Question 200 characters left Include your email address to get a message when this question is answered. Submit Advertisement

Tips

• Try to stay positive while you’re texting the guy so you have fun and exciting conversations. Assuming he has good intentions prevents any miscommunications.[18] Thanks Helpful 3 Not Helpful 0

Submit a Tip All tip submissions are carefully reviewed before being published Name Please provide your name and last initial Submit Thanks for submitting a tip for review! Advertisement

Warnings

• Only send appropriate pictures since unsolicited sexual images could make the other person feel uncomfortable.[19] Thanks Helpful 4 Not Helpful 1

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References

1. ↑ John Keegan. Dating Coach. Expert Interview
2. ↑ Julia McCurley. Certified Professional Matchmaker. Expert Interview
3. ↑ https://rendezvousmag.com/how-to-start-a-conversation-over-text/
4. ↑ John Keegan. Dating Coach. Expert Interview
5. ↑ Julia McCurley. Certified Professional Matchmaker. Expert Interview
6. ↑ John Keegan. Dating Coach. Expert Interview
7. ↑ Julia McCurley. Certified Professional Matchmaker. Expert Interview
8. ↑ https://www.seventeen.com/love/tips/g2366/flirty-texts/?slide=1
9. ↑ John Keegan. Dating Coach. Expert Interview

More References (10)

10. ↑ https://rendezvousmag.com/how-to-start-a-conversation-over-text/
11. ↑ Julia McCurley. Certified Professional Matchmaker. Expert Interview
12. ↑ https://rendezvousmag.com/how-to-start-a-conversation-over-text/
13. ↑ https://www.seventeen.com/love/tips/g2366/flirty-texts/?slide=5
14. ↑ https://www.psychologytoday.com/us/articles/200607/the-art-the-tease
15. ↑ John Keegan. Dating Coach. Expert Interview
16. ↑ John Keegan. Dating Coach. Expert Interview
17. ↑ https://www.sweetyhigh.com/read/how-to-let-text-conversation-die-013119
18. ↑ https://greatergood.berkeley.edu/article/item/six_tips_for_reading_emotions_in_text_messages
19. ↑ https://kidshealth.org/en/parents/2011-sexting.html

About This Article

Written by: John Keegan Dating Coach This article was written by John Keegan and by wikiHow staff writer, Hannah Dillon. John Keegan is a Dating Coach and motivational speaker based in New York City. With over 10 years of professional experience, he runs The Awakened Lifestyle, where he uses his expertise in dating, attraction, and social dynamics to help people find love. He teaches and holds dating workshops internationally, from Los Angeles to London and from Rio de Janeiro to Prague. His work has been featured in the New York Times, Humans of New York, and Men's Health. This article has been viewed 250,249 times. How helpful is this? Co-authors: 10 Updated: December 2, 2024 Views: 250,249 Categories: Texting In other languagesJapanese

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Yes No Advertisement Cookies make wikiHow better. By continuing to use our site, you agree to our cookie policy. Written by: John Keegan Dating Coach Click a star to vote Co-authors: 10 Updated: December 2, 2024 Views: 250,249

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