How To Ask A Guy Out Via Text

Maybe there’s a guy at work who you always get along with, a friendship you’d like to transition into something more, or even just a guy you matched with on Tinder. Rather than waiting for these guys to make the move, take that big first step and ask him out over text. Just like in person, you’ll want to be your best self to increase the odds that you’ll be getting that “yes.” Here’s how to do it.

  1. Build a great text connection. While it may seem bold to ask him out over text without any previous conversations, you’ll have better odds if you create a solid foundation. Even if you already know the guy in real life, don’t ask him out right away if you’ve never texted before. By developing a friendly text relationship first, the turn to a serious topic will come much easier. Plus, textual chemistry is a surefire sign that you’re meant to be.
  2. Start the conversation casually. You’re ready to ask him out. Great! But don’t jump the gun. Start the conversation as you always do. Maybe you watched an episode of a show he suggested or you have a fun inside joke you always bring up. Start there.
  3. Gauge his receptiveness to the conversation. Often, when you set your mind to something, it can be hard to hold off. “I’m going to ask him out right now!” But if he’s stressed out at work or sick and thus isn’t in a good mood through text, hold off. You can always ask him out tomorrow.
  4. Begin with a preamble. Rather than asking him out of nowhere, give a little preamble. When there’s a natural lull in the conversation, start asking him out with something like, “Hey, I was wondering…” This clues him in that you’re about to take things a step away from how your friendly relationship has always been.
  5. Make your intent clear. One of the biggest worries when asking someone out is whether or not they’ll understand what you’re asking. You’ve likely heard stories of going on a date only for one person to think it was just a friendship hangout. Awkward! Avoid this by making your intention clear. Try something like, “I’ve really enjoyed our talks at work,” or “You’re so good at making me smile.” Personalizing the text with a compliment and a description of how they make you feel is always a good opener.
  6. Suggest a meetup. Here’s where you get to the meat of the text. Avoid vague “hang out sometime” or “go out sometime” and instead say something specific. What would you want to do on this date? He’ll appreciate that you’ve been thinking about this and that some of the date planning has been taken out of his hands.
  7. Put it all together in one text. Avoid the urge to spread all of this out into multiple texts. A wall of texts is a surefire sign that someone is feeling insecure. Instead, show off your lovely confident vibes by asking him out in only one text. Putting everything together, that one text should look something like this: “Hey, I was wondering…I’ve enjoyed our conversations so much. You’re hilarious and really make me smile. Do you want to go to that new tapas place sometime soon?” Then, hit send.
  8. Give a little space and let the question breathe. While sending this text when you’re already having a nice conversation increases the odds that you’ll get a quick response, it isn’t a guarantee. You might be taking him off guard and he’ll need some time to think (or text his other friends to say “Holy crap! She just asked me out! Hell yeah!”). You might get the urge to fill the silence with another text. Do yourself a favor and stay away from your phone until you get a response from him. Don’t text “Just kidding.” Don’t text “Are you there?” Just let the silence breathe.
  9. Clear up any confusion. If you’ve been friends for a long time, there’s a chance he might be worried that he’s reading your text wrong. Even if you’ve been explicit and used the word “date,” he still might worry that if he’s interpreted this wrong, he might mess things up. If he comes at you with, “Are you being serious?” or “Do you mean a date? Like a date-date?” take this opportunity to further your message. “Yeah, I’ve had feelings for you for a while and thought this would be a good time to make a move.” Stick to your guns, girl.
  10. Accept the results with an open heart. If he said yes? Hell yeah, you did it! Time to celebrate! But if his reaction isn’t a resounding yes? Rejection can be tough, but it happens to everyone. Don’t take his “no” as an attack on your worth. You’re lovely and will find someone who agrees. Try to avoid taking the rejection personally. Of course, that’s easier said than done, so it doesn’t hurt to pick up a pint of ice cream, either.
Trisha is a full time writer living in Montana. In her free time, she paints mountainscapes on her skin with body paint and reads a ton of YA lit.