How to Get a Guy to Ask You Out Online

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So you’ve been chatting up a guy online and you’re feeling like you’re ready to take things to the next level, but you just can’t seem to make it happen. Never fear! Whether he’s shy, unsure, or totally clueless, there are plenty of ways you can try to get a guy to ask you out online. To help you do it, we’ve put together a list of tips and strategies you can use to hopefully land your dream date.

1

Tell him you’d love to meet up sometime.

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  1. If you’ve been talking online for a while and things are going well, try just casually mentioning that you’d like to meet IRL (in real life). He may take advantage of the moment and propose a date idea. [1] And just like that, he’s asked you out! [2]
    • The conversation could go like this: you could say, “It’s so fun talking to you, I hope we can meet up sometime” and then he could say, “Me too! How about dinner this Friday?”
    • You could also keep it playful and say, “I hope you’re this charming and funny in person!” He may respond with something like, “Why don’t we find out? Wanna grab a coffee Sunday afternoon?”
    • If he’s a little hesitant or doesn’t seem enthusiastic about meeting you, try keeping it lighthearted by saying, “Who knows, maybe one day we’ll actually get to meet face-to-face if the universe wants it.”
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2

Drop a major hint that you’d go out with him.

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  1. If you like the guy and you’d love for him to ask you out, why not just tell him? It could really boost his confidence and make him feel like it’s a sure thing. [3]
    • You could try, “You’re so fun to talk to you. If you asked me to dinner, I don’t know how I could say no.”
    • You could also be a little teasing with something like, “Oh no! I think we may actually have some chemistry here. I sure hope you don’t ask me out…”
    • If he doesn’t take the bait, don’t force it too much. He may come around eventually!
3

Make a joke about him asking you out.

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  1. If you’ve had a great back and forth with a guy and you just seem to have the same sense of humor, take advantage of it. Make a corny joke about getting his advice for a date or asking him if he knows anybody available for a date. He may play along with you, and while it started as a joke, it could easily end up as a real date! [4]
    • For instance, you could say something like, “I don’t know what to do. I really want to see this new movie on Friday night, but I don’t know any guys that I’ve been messaging on an almost daily basis who might be interested in going with me. Do you know anybody?”
    • You could also try, “I seem to be all out of dates for this weekend. I wish there was someone who could help me out.”
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4

Ask about a hypothetical date.

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  1. Make him feel more confident about asking you out and less worried about being rejected by playfully talking about going out together. Kill two birds with one stone by coming up with a fun date idea while also getting him to ask you out! [5] [6]
    • You could ask, “If we were going out on a date, where would you want to go?” It could lead him to eventually ask if you’d like to go out with him.
    • You could also tease him a bit with something like, “Here’s the thing: I love food. It’s very important to me. So I need to know where you’d take me to eat if we ever went on a date.”
5

Talk about weekend plans.

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  1. Everybody loves the weekend! He may have some time off from work or some free time he can use to potentially go out on a date. Tell him that you don’t have any plans and ask him what he’s up to. He may ask you to join him if he already has plans or he may ask you if you want to get together since you’re both free. [7]
    • You could try, “I’ve got nothing going on this weekend, what about you?” He may say something like, “Me either! Wanna go see a movie?” or he could say, “I’ve got this boring work party, any chance you want to come and make it more interesting?”
    • If he doesn’t seem interested in getting together, you can easily deflect and keep the conversation going with something like, “No problem if not, we can always try again in the future!”
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6

Mention something you’ve been wanting to do.

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  1. Talk about a movie you’ve been wanting to see, a restaurant you’ve been wanting to try, or a coffee shop you’ve heard is really cool. Tell him how fun it would be to go check it out and he just may pick up on the hint. [8]
    • You could try, “I’ve heard this bar has a typewriter you can use to write a poem, isn’t that cool?” He may respond with, “That is super cool, you wanna go check it out this weekend?”
    • You could also try, “I’ve heard the new Fast and Furious movie is terrible, but I kinda wanna see it.” He might say, “Yeah, there’s no way it’s good. Let’s go find out on Friday!”
7

Play the waiting game.

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  1. If you’re really shy, you don’t know him super well, or you just aren’t quite sure how you feel about him yet, don’t worry about it! You can still enjoy messaging him back and forth and seeing where things go. If you have great chemistry and he starts to really like you, he may feel comfortable just asking you out. [9]
    • There’s nothing wrong with taking your time and letting your relationship develop organically as you get to know each other online.
    • Try not to come on too strong by sending a ton of messages in a row or by getting upset if he takes a while to get back to you. It could make you look desperate or drive him away.
    • If he doesn’t seem to be making any moves, you may want to consider dropping some hints here and there that you’d like to go out with him.
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8

Flirt with him a bit.

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  1. It may seem a little obvious, but if you want a guy to like you, let him know that you’re into him by flirting with him! Spice up the conversation with some playful teasing and make it clear that you’re interested in more than just being friends. [10] He may take the hint that you’re into him and ask you out. [11]
    • For instance, if he says something like, “Work was a pain, had a super stressful day,” you could respond with something like, “Sorry to hear that. I bet I could make you feel better.”
    • You could also try flattering him a bit with something like, “Well, someone who’s super hot like you probably doesn’t have any problems getting a date.”
9

Try to be relaxed and laid-back.

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  1. It can be nerve-wracking trying to get a guy to like you and ask you out but don’t let him see you sweat. Play it cool and calm whenever you’re messaging each other back and forth. Don’t make a big deal about it if he takes a while to respond to your messages or if he doesn’t pick up on any of your hints that you want him to ask you out. It could actually make him want to chase after you even more. [12]
    • For instance, if he replies to a message hours after you sent it to him and says something like, “So sorry to take so long to get back to you! Got caught up at work.” Send a casual response like, “No worries, I was running around all day anyways.”
    • You could also play it a little cheeky. If he sends you a message after not communicating for a few days, you could say something like, “Oh, look who it is! It’s not like I was sitting here waiting around for you. Just kidding, how have you been?”
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10

Flip the script and ask him out.

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  1. Maybe he’s really shy or he’s just not catching that you’re into him, but whatever the case may be, you don’t have to wait around if you don’t want to. Be direct and go get him if you want him! [13]
    • You could try, “I’ve been wanting to check out this new art exhibit and was planning to go on Saturday. Do you want to come?”
    • You could also try, “One of my favorite bands is playing a show Friday night. You wanna go with me?”
    • Reader Poll: We asked 1981 wikiHow readers about which first date they’d like to go on the most, and only 8% said going rock climbing . [Take Poll] So, suggesting a more casual activity, like grabbing coffee, might be more fun for him.
    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

    Planning something in-person helps you build a solid connection. While there's nothing wrong with chatting online, in-person activities are the way to go when it comes to building successful relationships.

How Do You Ask Someone Out Over Text?


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      Tips

      • Try not to rush things if you just starting talking to a guy online. Take your time and enjoy talking to and getting to know them. If there’s real chemistry there, he may ask you out without any effort on your part.
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      Warnings

      • If you’ve never met him before, make sure he is who he says he is. If he has a profile picture, run it through a reverse-image search on Google to make sure it’s real. Check out his social media to make sure it doesn’t look fishy or like it’s a fake account. [14]
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      References

      1. ↑ Maya Diamond, MA. Relationship Coach. Expert Interview. 17 January 2019.
      2. ↑ https://www.huffpost.com/entry/online-dating_b_1401185
      3. ↑ https://upjourney.com/how-to-get-a-guy-to-ask-you-out
      4. ↑ https://upjourney.com/how-to-get-a-guy-to-ask-you-out
      5. ↑ Maya Diamond, MA. Relationship Coach. Expert Interview. 17 January 2019.
      6. ↑ https://upjourney.com/how-to-get-a-guy-to-ask-you-out
      7. ↑ https://www.huffpost.com/entry/online-dating_b_1401185
      8. ↑ https://www.huffpost.com/entry/online-dating_b_1401185
      9. ↑ https://www.today.com/health/snag-man-let-him-do-chasing-2D80555256
      1. ↑ Maya Diamond, MA. Relationship Coach. Expert Interview. 17 January 2019.
      2. ↑ https://pandagossips.com/posts/294
      3. ↑ https://stylecaster.com/10-tactics-get-guy-ask-you-out/
      4. ↑ https://stylecaster.com/10-tactics-get-guy-ask-you-out/
      5. ↑ https://www.rainn.org/articles/online-dating-and-dating-app-safety-tips

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