How to Play It Cool over Text

Written by John Keegan | Edited by Hannah Madden

Last Updated: May 28, 2022 References

It’s such a great feeling to finally land your crush’s number—but figuring out what to say and when to say it can put a lot of pressure on you and your texting skills. By playing it cool and sending the right messages, you can win your crush over and keep them interested. Read through our helpful tips to figure out what kind of messages to send and when you should send them to your crush.

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

Send one text at a time.

Double texting shows that you’re kind of desperate for an answer. If you want to play it cool, send them 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.

2

Keep your texts short.

Long texts can be a little off-putting. To play it cool, keep your texts short and sweet, and avoid sending long paragraphs. That way, they can easily read them 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 they won’t come off as strong as long texts would.

3

Let them text first sometimes.

Initiation should be about 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 that they’re at least mildly interested in talking to you (which is a good sign).

4

Keep your texts positive.

Complaining about lots of things could be a little off-putting. It’s totally fine to vent about a bad day every once in a while, but if all your texts are negative or talking about drama, your crush might lose interest. Try to keep your messages mostly upbeat and positive so that your texting buddy looks forward to a message from you.
- A good way to do this is 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.”

5

Take a few minutes to respond.

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 exactly, but texting back instantly can make it seem like you’re just waiting by the phone for their text.
- 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.

6

Focus on your shared interests.

This is a great way to start a cool, casual conversation. If you and your crush share any favorite TV shows, hobbies, or sports teams, use that as an opening line. It’s way more engaging than “hi” or “hello,” and it shows that you’re interested in their life, too.^{[1]
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Expert Source

John Keegan
Dating Coach
Expert Interview. 29 June 2021.}
- 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.

Show them that you’re genuinely interested in their life. Ask them questions about what they do for fun, what their hobbies are, and who they hang out with.^{[2]
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Expert Source

Mark Rosenfeld
Dating & Relationship Coach
Expert Interview. 11 June 2021.} People generally love talking about themselves. If you keep the conversation on them and not you, you’re going to have a great time. ^{[3]
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Expert Source

Judith Gottesman, MSW
Matchmaker & Dating Coach
Expert Interview. 19 October 2021.}
- 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?”
- Try not to ask too many questions in a row, though. If you sound like you’re conducting an interview, it could be a little off-putting.^{[4]
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  Expert Source
  
  John Keegan
  Dating Coach
  Expert Interview. 25 May 2021.}

8

Talk about your plans for the day.

Show your crush that you aren’t just waiting around 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 that you can’t text for long because you’ve got a busy day ahead of you. 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.

The right compliment can tell your crush that you’re interested without going overboard. Pick out something that you like, like their sense of humor, their personality, or even their friendship. Tell them how much you appreciate it, but stick to one or two compliments per conversation.^{[5]
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Expert Source

Julia McCurley
Certified Professional Matchmaker
Expert Interview. 30 September 2021.} 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.”

10

Send a few flirtatious messages.

Show that you’re interested with some cheeky banter or a little teasing. By flirting subtly, you can let your crush know that you might like them while still playing it cool. Sprinkle in a few flirty messages here and there, like:^{[6]
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Expert Source

Julianne Cantarella
Dating & Relationship Coach
Expert Interview. 6 August 2021.}
- “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

Send them a meme.

Tell your crush that you’re fun and funny with a well-timed meme. If the conversation is a little lacking or you aren’t sure what to say next, grab a meme from Instagram or Twitter that makes you chuckle. Send it to your crush with something like, “This made me think of you!”^{[7]
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Expert Source

Suzanna Mathews
Dating & Relationship Coach
Expert Interview. 18 August 2021.}
- If you aren’t sure what to send, try searching “meme” on Instagram to find something that you like.

12

Use emojis to show your feelings.

Flirty emojis can spice up a message without going overboard. A few well-placed winks or kissing faces show your crush that 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.^{[8]
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Expert Source

Mark Rosenfeld
Dating & Relationship Coach
Expert Interview. 11 June 2021.} Try messages like:
- “Can’t wait to see you later! 😙”
- “Wish I was there with you right now 😉”

13

Let them know it’s not a booty call if you text late at night.

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, you can turn a potentially awkward situation into a funny one. Try something like:^{[9]
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Expert Source

John Keegan
Dating Coach
Expert Interview. 28 September 2021.}
- “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.”

14

Suggest a plan to hang out IRL.

Keep it vague to seem cool and casual. If you want to hang out with your crush in-person, don’t be afraid to ask them what their plans are for the weekend or if they’d like to chill sometime. Texting is great, but the best way to get to know someone is face-to-face.^{[10]
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Expert Source

John Keegan
Dating Coach
Expert Interview. 25 May 2021.} 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.”

15

Plan a group outing to be a little more subtle.

If you’re not sure whether they’re interested, try inviting 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!”

16

Move on if they’re not replying.

You deserve someone who doesn’t make you wait around for their response. If your crush isn’t responding or they never reach out first, they might just not be interested, and that’s okay.^{[11]
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Expert Source

John Keegan
Dating Coach
Expert Interview. 25 May 2021.} 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 that you’re moving on. Just don’t reach out first, and they’ll get the message.