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If you’re crushing on a guy, you’re probably pretty eager to text him as much as possible so you can get to know him better. If you want him to chime in every day, it’s so important to keep him interested and engaged. Luckily, we’ve got a ton of helpful tips and example messages you can try out so you can carry on a great conversation!

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1

Ask him about his day.

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  1. Keep it casual by asking how he’s doing if you’re not sure what else you should talk about. Ask if he has plans for the day or if he had anything exciting happen to him recently. Once he replies, keep digging for more details to carry on the rest of the conversation. [1]
    • For example, you might text, “Hey! How’s your day been going so far?” or “What’s the most exciting thing that happened today?”
    • Even if he doesn’t ask you, respond with what you’re up to as well since he might want to ask you more about it.
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2

Pose a few fun, open-ended questions.

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  1. Open-ended questions usually start with words like “what,” “how,” or “why” so he can’t just reply with one word. Learn more about the things he likes to do, ask him for a recommendation, or try out a silly icebreaker so you can get the conversation going. Once he answers, ask some follow-up questions so you can keep chatting. [2]
    • You could ask him, “What do you like to do in your free time?”
    • If you want to get his advice, try something like, “What movie do you think I should watch tonight?” or, “What games do you think I’d like to play?”
    • Fun icebreakers include, “What 3 things would you bring to a desert island?” or “What would you do if you had a million dollars?”
3

Bring up your common interests.

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  1. If you’re already friends on social media, look through his profile to find a few things that he likes to do. Casually mention what you find in one of your messages and let him know that you’re into it too! Ask him more to talk about it more so you can dig deeper and build up your connection. [3]
    • If he’s really into football, you could say something like, “The Ravens are my favorite team too! Who’s your favorite player?” or “OMG I love football! What did you think of the game last night?”
    • If he’s into art, you might say, “That’s so cool you’re into painting! Is there an artist that you really look up to?” or “I wish I knew more about art. Are there any museums you think I should check out?”
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4

Flatter him with a compliment.

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  1. If you’re feeling flirty, mention something that you really appreciate about the guy you’re chatting with. You could talk about his looks, personality, or anything else you admire about him. He’ll either thank you, or he may compliment you back if he’s interested in you too! Just be careful not to come on too strong if you started talking recently since it may make him a little uncomfortable. [4]
    • Say something like, “I saw your Insta pic! You’re so handsome in a suit! 🥰” or “I love seeing your smile!”
    • You might say, “You always know just how to make me feel so special,” or, “You have such a way with words, you could be a poet!”
5

Be a little mysterious.

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  1. Rather than telling the guy everything right away, end your message on an intriguing cliffhanger. He’ll be so curious about what you’re up to, he’ll reach out again to ask you for more. Give him a little more to work with in each reply so you can keep texting back and forth. [5]
    • Message him something like, “You would not believe what happened at work today…” or, “That reminds me of a funny story from when I was younger! You’re going to laugh so hard at this.”
    • If you want to be a little flirty, you might try, “I had a crazy dream about you 😉.”
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6

Send him a few pics.

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  1. Your guy will love seeing you having a good time, so snap a pic or record a video to give him a quick glimpse of what you’re doing. Ask him a question or add a fun, flirty caption to show him that he’s really missing out.
    • You could send him a selfie and say, “Just got a new outfit! What do you think?”
    • You could send him a picture of where you are and say, “This would be so much fun if you were here! Wish you could come too!”
    • Avoid sending any explicit pictures since they might make him feel a bit uncomfortable.
7

Make plans to meet up in person.

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  1. Even though texting is a great way to stay in touch, ask if he wants to meet up and do something together if you want a deeper relationship. Suggest a fun date or a casual hangout so you can get to know each other better and test out your physical chemistry. If you live far away or can’t easily get together, you can always try talking on the phone or hopping on a video call. [6]
    • You might ask, “OMG my favorite band is playing here this weekend! Do you want to come with me?”
    • You could say, “Do you want to grab a coffee and chat sometime soon?” or “Are you free for dinner on Friday? I’d love to see you 😊.”
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8

Have a reason for texting him.

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  1. Conversations can get pretty stale if you’re just texting without any reason. Whenever you send a text, work towards getting to know him better or planning a date. That way, you aren’t interrupting what he’s doing or making him bored.
9

Keep your messages lighthearted.

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  1. Texting isn’t a great way to have serious conversations since the guy may misread the tone of the message. Stick to fun topics and learning more about him with every message. If you ever need to have a deeper discussion, save it for chatting on the phone or when you meet up face-to-face. [7]
    • Reader Poll: We asked 625 wikiHow readers about the best ways to build a connection with someone they like over text, and only 8% of people recommended bringing up super deep, philosophical topics . [Take Poll] Instead, keep it light, fun, friendly, and sweet—save the serious topics for in-person conversation!
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10

Let him reach out first a few times.

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  1. If you’re always texting a guy, he might think that you’re always available. Rather than always being the first one to message him, put your phone away and wait for him to text you first. If he’s really interested and wants to continue the conversation, he’ll eventually reach out to talk to you. [8]
    • When he messages you, you can sometimes tell him that you’re busy to keep him on his toes. You might say, “Hey! So good to hear from you but I’m with friends right now. I can talk later though 🙂.”
11

Wait until he responds to message him again.

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  1. If your guy opens up his messages and sees a wall of text, he might not know what to respond to. If he doesn’t reply right away, he might just be busy or doing something else. Once he finally does respond, give it the same amount of time before you reply to him so it doesn’t seem like you were waiting by your phone.
    • If he only sends one-word responses or takes a few days in between replies, it may be a sign that he’s not interested. Move on and put your energy into someone else who wants to build a deeper connection with you.
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Join the Discussion...

WikiSkyDancer007
35
Ugh, I'm getting so flustered with this guy I've been texting lately! It feels like he has all the right things to say and is SO cute about it, a... Read More
3
Cher Gopman
Dating Coach
I think if you are trying to flirt through text messages, it's okay to use emojis here and there. You don't want to overuse them, because that'll... Read More
WikiMongooseChaser121
1
A little bit of joking or teasing can help create a playful mood that's good for flirting... Read More

Improve Your Texting Game with this Expert Series

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  • Question
    Will compliments keep a guy interested?
    John Keegan
    Dating Coach
    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.
    Dating Coach
    Expert Answer
    It might, but only do this sparsely. Just give them a compliment every now and then to keep them invested. If you overdo it, it might scare them off or come off as insincere.
  • Question
    How can I keep our conversations interesting?
    John Keegan
    Dating Coach
    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.
    Dating Coach
    Expert Answer
    Don't take it too seriously! If you come across something silly or funny, send it to them. Share a laugh over something totally random. Those kinds of little interjections keep conversation fresh and interesting.
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