Guys, should I text him to ask him out?

Background: I have met this guy about two months ago, we have met each other when we are with friends and he has flirted with me quite a bit in 'real life' and also through text. When we meet when we are with friends he looks at me and I can see he says things about me to his friends, but I think he doesn't have the guts to really start conversations with me (he only asks lame questions that don't lead to any conversations).. Problem is, out of the 5 longer texting conversations we have had over these two months, I started 4 (he did ask for my number though, and texts me back immediately all the time). I would like to get to know him better, but I am getting put off by the fact that he doesn't text me first.. I do know he is extremely busy, and working about 60 hours a week. Should I ask him out or just wait until he initiates something?


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Most Helpful Guy

  • You can start a conversation and let him know that you like listening to what he has to say. It should motivate him into conversing with you. Also, if you can get him to tell you some story.. like whatever was the craziest thing he's done in life or something silly.. you can react to his story to swap the roles and tell him afterwards you enjoyed it. Even if it's a boring story, try to be positive if you like the guy. It's not easy to open up personalities.

    It's not much but it's a start :)

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    • I don't see him in person that much, and if we meet, we only meet together with mutual friends..

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    • but wouldn't you say that if he was interested he would start a conversation himself once in a while? He seems eager to talk to me when I text him first, but I am thinking maybe he just texts back to be nice to me or something

    • Maybe he just expects you to start the conversations because he doesn't want to seem eager. Anyhow, you could always just ask him if he's into anyone. This should give you a clue while being casual-ish.

What Guys Said 1

  • Don't do it over text because you are giving him a chance to reject you.

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    • ok thanks, I wouldn't straight out ask him probably, first start a light conversation and if he responds well maybe ask ;) I don't have the guts to just ask him.

    • Woman up and just go for it lol

What Girls Said 1

  • I would ask him to hang out with you in person and if you are still feeling the same ask him out then. If you do he may admire your guts to say it in person! That maybe the type of person he needs :) I think either way it wouldn't upset him. But I feel like it is more close and personal when you are face to face since you can then read body language and all those awk but cute things people do when they first starting dating and such!!

    Overall: Do it in person but in text wouldn't kill you if you did!

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    • problem is I don't run into him occasionally, I only see him when we're with mutual friends, which happens about 1-2 times per month.. so that's why I am thinking if I'll text him because otherwise I won't see him for a month probably

    • Okay I would then text him to be like "Hey! Want to go to XX or Get XX with me?" Make it casual but he will wonder what's up since it will be just you two. I would get to know him better on a face to face level. But from the sounds of it you two are hitting it off really well right now! So just let him know you want to hang out with him. Again its up to you!! You really know the context of the relationship and I don't, do what feels right! :)

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