How to Play It Cool Over Text: The Best Flirting Techniques

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Draw your crush’s attention via text with these expert tips

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IN THIS ARTICLE

1 Send one text at a time.

2 Keep your texts short.

3 Let them text first sometimes.

4 Keep your texts positive.

5 Take a few minutes to respond.

6 Focus on your shared interests.

7 Ask them interesting questions.

8 Talk about your plans for the day.

9 Compliment them.

10 Send a few flirtatious messages.

11 Use emojis to show your feelings.

12 Send them a meme.

13 Suggest a plan to hang out IRL.

14 Plan a group outing to be a little more subtle.

15 Express your intentions if you need to.

16 Move on if they don’t reply.

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Written by John Keegan | Edited by Aly Rusciano

Last Updated: December 4, 2024 Fact Checked

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It’s such a great feeling to finally land your crush’s number, but figuring out what to say can be nerve-wracking. Believe us, we get it! Thankfully, there are plenty of ways you can play it cool, send the right messages, and win your crush over. We interviewed relationship and dating coaches to teach you how to master these texting skills, so keep reading to learn how to entertain and play it cool with your crush over text.

Steps

1

Send one text at a time.

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1. Double texting may come off as you being desperate for an answer. If you want to play it cool, send your crush one text at a time—and don’t be afraid to wait for their response. If you constantly text them over and over or ask, “Why aren’t you replying?,” they might feel a bit smothered and you could lose their interest.

   • People stop replying for all sorts of reasons. More often than not, it’s because they got busy with something else, not because they’re intentionally ignoring you, so don’t worry if your crush is taking longer than usual to reply!
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2

Keep your texts short.

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1. Long texts can be a little off-putting. As dating coach John Keegan puts it, “keep it simple.” Play it cool by keeping your texts short and sweet and refraining from sending long paragraphs. That way, your crush can easily read your texts and respond, and you’ll stay as cool as a cucumber to keep them interested.

   • Plus, shorter texts are a little easier to digest and won’t come off as strong as long texts would. It’s best to keep it casual when you can!

3

Let them text first sometimes.

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1. Initiating the messaging should ideally be a 50/50 split between you two. If you find that you’re always the one texting first, wait a little bit to see if they reach out. That way, you don’t feel like you’re putting in all the effort, and they see that they’re going to have to text first sometimes.

   • Plus, when someone texts you first, you know they’re at least mildly interested in talking to you (which is a good sign). If your text never initiates text convos with you, it may be time to move on to someone who’s more willing to put in the effort to get to know you.
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4

Keep your texts positive.

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1. Complaining about lots of things could rub them the wrong way. It’s totally fine to vent about a bad day every once in a while, but if all your texts are negative or talk about drama, your crush might lose interest. Try to keep your messages mostly upbeat so that your crush looks forward to your messages.

   • As an example, try to turn annoying or irritating situations into funny stories. For instance, if you were walking down the sidewalk and got splashed by an oncoming car, you might text your crush, “OMG, I’m gonna be so late to work today. I was walking down Main St. and totally got splashed by the bus. It was like a waterfall!! I had to run home and change super fast.”
   • 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!
   EXPERT TIP

   

   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.

   

   John Keegan
   Dating Coach

   Avoid talking about heavy topics right away. Stay away from politics or other deep issues in the initial stages of talking. Instead, opt for light-hearted topics to keep it playful and light.

5

Take a few minutes to respond.

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1. Try to match their response time so you don’t seem too eager. If they take an hour to respond, feel free to wait about 45 minutes before you reply. You don’t have to follow this rule exactly, but texting back instantly can make it seem like you’re just waiting by the phone for their text.

   • However, some people may argue that it’s even cooler to not care what your crush thinks and avoid playing any games. If they took awhile to text you back but you see their text and want to respond to them, you do you!
   • Try not to take long response times personally—a lot of people are just bad texters, and they lose track of who texted them when.
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6

Focus on your shared interests.

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1. A cool, casual conversation can start with common interests or hobbies. If you and your crush share any favorite TV shows, hobbies, or sports teams, use that as an opening line. As Keegan explains, asking about hobbies is way more engaging than a simple “hi” or “hello” and shows that you’re interested in their life.

   • For instance, you might say, “Did you see the new season of Riverdale? I have so many questions…”
   • Or, “Gone frisbee golfing lately? I want to try that new course down by the waterfront!”

7

Ask them interesting questions.

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1. Showing a genuine interest in their life can keep the conversation going. Relationship coach Mark Rosenfeld advises asking them questions about what they do for fun, what their hobbies are, and who they hang out with. People generally love talking about themselves. Plus, as matchmaker Judith Gottesman says, this is a great way to “find things you have in common to connect on.”

   • Ask questions like: “What are you up to this weekend?” “What do you like to do to relax?” and “What’s your favorite activity to do outside the house?”
   • But as Keegan advises, try not to ask too many questions in a row. It could be a little off-putting if you sound like you’re conducting an interview.
   EXPERT TIP

   

   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.

   

   John Keegan
   Dating Coach

   Think of your text conversation as an ongoing conversation, rather than a virtual chat. What can you ask that’s engaging and will get your crush talking? In other words, what will keep the conversation going?
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8

Talk about your plans for the day.

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1. Subtly show your crush that you aren’t just waiting for their text. If they ask what you’re up to, feel free to share any plans you’ve got going on, like hanging out with friends or heading to the beach. You could even tell them you can’t text for long because you have a busy day ahead. They’ll realize that you have a life outside of them, and it will make you seem like a well-rounded, cool person.

   • For instance, you could say, “I’m about to grab a couple of drinks with friends. What are you up to tonight?”
   • Or, “Sorry, can’t talk long! I’m heading to the beach to catch some rays.”

9

Compliment them.

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1. The right compliment can show you’re interested without going overboard. As matchmaker Julia McCurley says, “Complimenting your crush is a good way to renew the sparks.” Pick out something that you like about them, such as their sense of humor or personality. Tell them how much you appreciate it, but stick to one or two compliments per conversation. That way, you’ll flatter them while still being cool and casual. Try something like:

   • “You’re so funny! Your texts always make me laugh.”
   • “You’re such a kind person. I’m really lucky to have you in my life.”
   • “No wonder you have so many friends! You’re such a giving person.”
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10

Send a few flirtatious messages.

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1. Some cheeky banter or teasing is an excellent way to show your interest. By subtly flirting, you can let your crush know you like them while still playing it cool. Sprinkle in a few flirty messages here and there, like:

   • “Wow, reading about physics on your day off? Didn’t know I was texting with a genius 😉”
   • “I had a dream about you last night!”
   • “Stop thinking about me so much! I can’t sleep if I’m busy running through your mind all night!”

11

Use emojis to show your feelings.

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1. Flirty emojis can spice up a message without going overboard. A few well-placed winks or kissing faces show your crush you’re interested, but it doesn’t seem desperate. However, you should try to match their emoji style—if they don’t use emojis at all, you might want to hold off, per Rosenfeld’s advice. Try messages like:

   • “Can’t wait to see you later! 😙”
   • “Wish I was there with you right now 😉”
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12

Send them a meme.

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1. A bit of humor can go a long way in showing your crush your personality. If the conversation is a little lacking or you aren’t sure what to say next, Dating coach Suzanna Matthews suggests grabbing a meme from Instagram or Twitter that makes you chuckle. Send it to your crush with something like, “This made me think of you!”

   • If you aren’t sure what to send, try searching “meme” on Instagram to find something that you like.

13

Suggest a plan to hang out IRL.

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1. If you want to hang out with your crush in person, don’t be afraid to ask! Keep it vague to seem cool and casual. Ask them what their plans are for the weekend or if they’d like to chill sometime. Texting is great, but as Keegan clarifies, the best way to get to know someone is face-to-face. Try messages like:

   • “Have you heard about that new bar downtown? I was thinking of trying it out this weekend if you’d like to join me.”
   • “What are you up to this weekend? If you have any free time, I’d love to grab some coffee.”
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14

Plan a group outing to be a little more subtle.

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1. If you don’t know if they’re interested, invite them to a “friend” outing. See if a couple of your buddies want to meet up and do something fun, like grabbing a drink or going on a hike. Then, you can invite your crush along, just to keep things casual. Try something like:

   • “My friends and I were thinking of hitting up that new restaurant on the waterfront tonight. Want to join us?”
   • “If you don’t have any plans on Sunday, I think me and some buddies are gonna go hiking. You’re welcome to come along!”

15

Express your intentions if you need to.

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1. If you’re texting late at night, let them know it’s not a booty call. Late-night texts tend to insinuate that you only want to hook up. If that’s not the case, but you’d still like to send a text late at night, tell your crush that you’re texting them genuinely and you aren’t looking for them to come over right now. If you make it into a joke, Keegan says you can turn a potentially awkward situation into a funny one. Try something like:

   • “Hey! I know it’s late. I promise I’m not trying to make you a booty call lol. What are you up to?”
   • “People who text this late are usually looking for a booty call, huh? Haha, good thing I’m not like that.”
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16

Move on if they don’t reply.

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1. You deserve someone who doesn’t make you wait around for their response. Keegan explains that if your crush isn’t responding or they never reach out first, they might just not be interested, and that’s okay. There are plenty of fish in the sea, and you can find someone else to text you back quickly.

   • You don’t need to tell your crush you’re moving on. Just don’t reach out first, and they’ll get the message (or they may even start reaching out themselves).
   EXPERT TIP

   

   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.

   

   John Keegan
   Dating Coach

   If someone likes you, they’ll make texting easy! They’ll respond quickly, engage in conversation, and text you first. If they make it hard, it’s usually a sign they’re not really that interested.

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Tips

• Dating coach Julianne Cantarella points out that “we always know when someone’s flirting with us by their tone.” So, if they’re complimentary or use a lot of flirty or happy emojis in response to your texts, they may be into you too!
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• When someone texts “cool,” they’re usually approving or agreeing with something.
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• When someone says “cool it” in a text, they’re saying, “You need to calm down.”
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