How to Restart a Conversation with a Guy

Co-authored by Cher Gopman and Janice Tieperman

Last Updated: August 25, 2021 References

You’re chatting with this guy, and you feel like there’s a real connection… until he stops replying. Don’t worry. There are plenty of ways to jumpstart your conversation to get things moving again. We’ve put together some clever ideas that may catch his interest.

1

Acknowledge that it’s been awhile.

Mention the elephant in the room before restarting the conversation. Jokes and one-liners are a great way to break the ice, but they aren’t your only option. Basic, simple messages like “Hey stranger” or “It’s been awhile” are also great ways to restart the conversation.^{[1]
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- You might say, “Long time no see! How are you doing?” or “Hey stranger! What’ve you been up to?”

2

Follow up on previous topics.

Re-read your past messages so you know where you both left off. Pick out one of the topics you discussed earlier, and recycle that topic into your conversation now. You could also shoot him some questions about his family, hobbies, or interests.^{[2]
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- You could say, “How’s the soccer season going?” or “You mentioned you applied to a couple universities earlier. Have you heard back from them?”
- “Watch any good movies lately?” or “Did you hear they’re rebooting this TV show?” are other great ways to restart a conversation.

3

Send an intriguing message.

A vague but interesting message may leave him wanting to know more. Cryptically mention something cool or funny that happened to you recently, or something exciting that happened in your life. Pose this cool, exciting event as a vague question or statement, like “You won’t believe who I just saw!” Chances are, he might be interested enough to reply.^{[3]
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- You could say, “You’ll never guess where I was last weekend!” or “Something unbelievable just happened to me in class today.”
- You might also say, “Something crazy just happened to me, and I just had to tell someone.”

4

Compliment him.

Inflating his ego is a great way to get a reply. You don’t need to go over-the-top for this—a simple, sincere compliment is a great way to break the ice after a long pause in a conversation. Mention how nice he looked today, or make a sweet comment about how he’s on your mind.^{[4]
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- You could say something like, “You look like you were born to wear that hockey jersey” or “Congrats on making the debate team!”
- You might also say, “Man, I need a new TV show to binge. You have excellent taste—what shows do you like?”

5

Ask for his opinion.

If you send an interesting question, there’s a good chance he'll answer. Ask for his opinion on something, whether it’s school-related, sports-related, or something completely random.^{[5]
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Cher Gopman
Dating Coach
Expert Interview. 17 May 2019.} There’s a good chance he’ll message you back to share his opinion.^{[6]
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- You might say, “What do you think about this band?” or “If you could have 1 billion dollars or speak every language in the world, which would you choose?”

6

Offer a fun assumption about him.

Pretend you know something about him and see if he confirms it. Send a friendly message voicing your guess. He might reply so he can confirm or correct your assumption. Plus, these comments are a great way to give him a subtle compliment!^{[7]
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- You might say, “You look like you could run a mile in 6 minutes” or “You must spend 2 hours getting your hair to look so good.”
- You could also say, “You seem more like a cat person than a dog person,” or “I bet you’re a secret genius at physics.”

7

Send him a meme.

A good meme is worth a thousand words. Look through your old photos and saved pictures for a funny meme or picture you can send over. If he gets a laugh out of it, he just might reply.^{[8]
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- You could do a play on the classic Bernie Sanders meme and send an edited picture that says, “I am once again asking for the answers to tonight’s math homework.”
- You could also send a gif or screenshot that you think he’d find funny, like a silly animal or a scene from a popular TV show.

8

Pretend to message him by accident.

Random messages are a fun, spontaneous way to get his attention. Send him a random emoji, or something similar. Then, send a follow-up message explaining that you messaged him by accident. Transition this “mistake” into a new conversation!^{[9]
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- You might send a random key-smash of letters, and then say, “Oops! I didn’t mean to send that. But while I’m here, howdy stranger!”
- You could send him a random GIF, and then comment, “Whoops, wrong person!”

9

Offer a funny one-liner.

One-liners are a silly way to restart your old chat. You might send something simple like, “I’m just going to shoot my shot here,” or you could make a bolder move, like inviting him to ask you out. Play around with different jokes and one-liners until you find something that works for you!^{[10]
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- If you’re reviving an old Tinder or Bumble conversation, you could say, “I think you forgot to ask for this!” and then provide your cell phone number.
- “How long have you been waiting for me to reply again?” or “Are you waiting for me to come to you? If so, you win!” are some clever lines you could try.

10

Be sarcastic.

If he has a dry sense of humor, an ironic message could do the trick. Create a witty, sarcastic crack on how he hasn’t replied to you in a while. This might be hit or miss, but there’s a chance that he’ll enjoy the sarcasm and shoot you a message back.^{[11]
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- You could say, “Wow, you’re really chatty today!” or “You’re typing so fast that I can barely keep up!”

11

Change the format of your conversation.

Switching from texts to images might get his attention. Instead of shooting him a message, send him a picture, GIF, or voice memo message instead. If you’re feeling especially bold, you could even invite him to video chat with you.^{[12]
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Expert Q&A

Question

How do you revive a dead conversation?

Cher Gopman
Dating Coach
Cher Gopman is the Founder of NYC Wingwoman LLC, a date coaching service based in New York City. 'NYC Wingwoman' offers matchmaking, wingwoman services, 1-on-1 Coaching, and intensive weekend bootcamps. Cher is a Certified Life Coach, a former psychiatric nurse, and her work has been featured on Inside Edition, Fox, ABC, VH1, and The New York Post.

Cher Gopman

Dating Coach

Expert Answer

Ask an open-ended question. People generally enjoy talking about themselves, and asking questions will get them to open up and talk more.
Question

How do I let them know I'm interested if I said I wasn't in the past?

Cher Gopman
Dating Coach
Cher Gopman is the Founder of NYC Wingwoman LLC, a date coaching service based in New York City. 'NYC Wingwoman' offers matchmaking, wingwoman services, 1-on-1 Coaching, and intensive weekend bootcamps. Cher is a Certified Life Coach, a former psychiatric nurse, and her work has been featured on Inside Edition, Fox, ABC, VH1, and The New York Post.

Cher Gopman

Dating Coach

Expert Answer

Keep talking to them. Maintain that conversation and let them know you aren't going anywhere. Express a genuine interest in what they're up to. Over time, they'll realize that you are actively trying to be a part of their life and you can go from there.

Warnings

There’s nothing wrong with restarting a conversation, but don’t wait endlessly for a response, either. Your time is just as valuable as his!^{[15]
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