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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.

4

Keep your texts positive.

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  1. 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.”
    • Reader Poll: We asked 432 wikiHow readers about the best ways to build a connection with someone they like over text, and only 7% 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!
7

Ask them interesting questions.

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  1. Ask them questions about what they do for fun, what their hobbies are, and who they hang out with. [2] 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]
    • 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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8

Talk about your plans for the day.

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  1. 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.

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  1. 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] 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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13

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

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  1. 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]
    • “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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15

Plan a group outing to be a little more subtle.

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  1. 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!”
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      References

      1. John Keegan. Dating Coach. Expert Interview. 29 June 2021.
      2. Mark Rosenfeld. Dating & Relationship Coach. Expert Interview. 11 June 2021.
      3. Judith Gottesman, MSW. Matchmaker & Dating Coach. Expert Interview. 19 October 2021.
      4. John Keegan. Dating Coach. Expert Interview. 25 May 2021.
      5. Julia McCurley. Certified Professional Matchmaker. Expert Interview. 30 September 2021.
      6. Julianne Cantarella. Dating & Relationship Coach. Expert Interview. 6 August 2021.
      7. Suzanna Mathews. Dating & Relationship Coach. Expert Interview. 18 August 2021.
      8. Mark Rosenfeld. Dating & Relationship Coach. Expert Interview. 11 June 2021.
      9. John Keegan. Dating Coach. Expert Interview. 28 September 2021.
      1. John Keegan. Dating Coach. Expert Interview. 25 May 2021.
      2. John Keegan. Dating Coach. Expert Interview. 25 May 2021.

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