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Even the most confident-looking people out there get butterflies in their gut when it comes to talking to their crush. You are not weak for taking a pause here—especially if you don’t have decades in the dating game. The good news is that all of this is going to be much easier as soon as you can push yourself to take that first step and push “send.” Once the first text is out there, you can just let the conversation develop organically. In the meantime, if you need an extra boost of courage or confidence, you’re in the right place!

This article is based on an interview with our professional dating coach, Cher Gopman, founder of NYC Wingwoman LLC. Check out the full interview here.

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1

List your best qualities for a self-esteem boost.

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  1. You can either grab a pen and paper and start writing, or just talk out loud to yourself. Start with something small that you really like about yourself and then work your way up to the big things that you’re really proud of. Remembering what makes you special will put you in a better head state to text your crush.[1]
    • You might start with something small and physical, like your hair or your height. Then, you might consider skills or talents, like your ability to write or your mastery of a certain sport. Finally, remind yourself of all of the great things that make you, you. Your compassion, your kindness, your ingenuity, etc.
    • If nothing immediately comes to mind, ask your best friend or parent about what they like about you. Sometimes, it really helps to hear it come out of someone else’s mouth!
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2

Strike a power pose for some quick courage.

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  1. It sounds totally silly, but striking a quick pose in the mirror will literally make you more confident. Take that shirt off, flex your biceps, throw your arms in the air like you just won a marathon, or hold your fists up like you’re about to get into a fight and let out a guttural growl. Feel goofy? Probably. But science says you’re going to be way more courageous than you were before![2]
3

Ease your nerves with some controlled breathing.

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  1. Controlled breathing is a great option if you just need to settle your mind before you try and lay down some game.[4] There are a lot of ways to do this, but the easiest is to simply breathe in through your nose, feel the air expand in your lungs and belly, and then breath out slowly through your mouth. Repeat as needed until you’re feeling as cool as a cucumber.[5]
    • If you’re more of a “pump some iron to calm down” kind of person, feel free to just exercise however you normally would. This is another great way to calm down and get some stress off.[6]
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4

Remind yourself it isn’t a big deal.

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  1. Think about it this way; all you’re really doing is typing out a few words and hitting the send button, right? Remind yourself that this isn’t all that deep, even if it really feels like it right now. If you can just trick your heart into listening to your head, this will be so much easier.[7]
    • A lot of people are way too tense when they talk to their crush. If you’re going to seal the deal, you want to come off as smooth, genuine, and laid-back. You can’t be any of those things if you keep thinking this is super serious!
6

Achieve a small win or two.

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  1. Even if it’s something as small as rearranging your room the way you’d been meaning to, or beating a tough boss in a video game, go do it. Pick something small that you can easily cross off of your to-do list and get to work. Not only will you feel better in the moment, but you’ll get a big dose of confidence to get your courage up for the big text message.[9]
    • If you really want to build some momentum, accomplish 3 small goals over the course of the next 3 days, then text your crush. You’ll have more than enough courage to do it by then!
7

Take your time to cool off.

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  1. There’s no need to force yourself to do this right now (or even today) if you aren’t ready. If you’re not in the most confident, courageous state of mind, no worries. Take a deep breath and relax. If you need to do something else to wind down right now, go for it. You’ve got all the time in the world.[10]
    • One of the worst mistakes people make when talking to their crush is that they try too hard. You want to be your genuine, authentic self. If you aren’t feeling particularly like you right now, don’t push yourself to say something you might regret.[11]
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8

Embrace the nerves.

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9

Draft out a shorter text if this is a first interaction.

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  1. If this is the first time you’re texting them, short is sweet. Aim for something a little more interesting than “hey,” but don’t write a huge paragraph if you’re just getting to know one another. Aim to shoot them a text when you know they’re probably up and able to chat. Remember, your goal here may be to simply get the conversation started.[13] You might say:
    • “Hey, this is Sarah from calculus. I know we haven’t talked much, but did you do the homework? I’m really struggling.” From there, get some “help” and then just ask them how their day was to try and establish a friendship.
    • “Hey Stacey! This is Nick, from the party. How are you?” Then, just chat and get to know them.
    • If you’ve already chatted in real life, you could even open with a random funny gif, or a meme that you think they’d like.
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10

Compose a flirty message if you want to test the waters.

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  1. The moment you move just from casual chatting to flirting can feel like a momentous occasion. Remember, they don’t know you’re trying to flirt, so there’s no need to be tense! You could aim to lean into a shared interest and bond over that, or pay them a compliment that implies you’ve been thinking about them.[14] You might try:
    • “Have you seen this new Batman movie yet? It looks interesting and I know you love comics as much as I do. We should see it sometime!” If things go well, you might say, “It’s a date!” if they seem a little hesitant, you can always back off and just say you should hang out as friends.
    • If the two of you both love The Office, lean into it with something like, “You and I should team up like Jim and Pam to prank my annoying coworker. I’ve had such a long day at work, how are you?”
    • “I loved that dress you wore today. Super cute stuff. Where do you get your sense of style?”
    • Throw a flirty emoji in there with your message. The raised eyebrow emoji or the hearts-for-eyes face are great ways to build some romantic tension.[15]
11

Let them know how you feel if the vibe is right.

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  1. If you’ve worked up the courage to finally tell them how you feel, congratulations! This takes guts, but you’ve got this! Draft your message and scan it a few times to make sure you’re happy with the way it reads. Try to keep this low-key and don’t put any pressure on them.[16] You could try:
    • “Hey, I’m sorry if this is a lot, but I’m going to kick myself if I don’t say it. I think you’re neat and I’d love to take you out some time!”
    • “I really hope this isn’t too out of nowhere, but I’ve developed feelings for you. Would you be interested in going out sometime?”
    • “Okay, I’m just going to say. You’re cute, I’m cute, we should go out.”
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13

Send it and wait for a response.

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  1. It’s possible that they’re busy when you texted them, or maybe they’re just thinking about what to say. It’s even possible they like you and they’re just going to play a little hard to get. In any case, put the phone down if they don’t respond right away and relax. Once they respond, keep the conversation moving organically and stay cool.[18]
    • If you send multiple texts after you’ve texted them once, no good is going to come of it. They’re either going to feel like you’re overwhelming them, or they’re going to get annoyed that their phone keeps going off while they’re busy. Remember, play it cool!
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  1. Imad Jbara. Dating Coach. Expert Interview. 5 November 2019.
  2. Imad Jbara. Dating Coach. Expert Interview. 5 November 2019.
  3. https://www.fastcompany.com/3022177/feeling-anxious-why-trying-to-keep-calm-is-a-terrible-idea
  4. https://www.businessinsider.com/how-to-text-someone-you-want-to-date-2017-2
  5. Cher Gopman. Dating Coach. Expert Interview. 17 May 2019.
  6. Cher Gopman. Dating Coach. Expert Interview. 17 May 2019.
  7. https://www.seventeen.com/love/dating-advice/a26324989/how-to-tell-someone-you-like-them/
  8. Imad Jbara. Dating Coach. Expert Interview. 5 November 2019.
  9. Cher Gopman. Dating Coach. Expert Interview. 17 May 2019.

About This Article

Cher Gopman
Co-authored by:
Dating Coach
This article was co-authored by Cher Gopman and by wikiHow staff writer, Eric McClure. 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. This article has been viewed 41,200 times.
42 votes - 79%
Co-authors: 7
Updated: May 28, 2022
Views: 41,200
Categories: Crushes
Thanks to all authors for creating a page that has been read 41,200 times.

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