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I started talking to this guy in one of my classes, and he asked me out for a date a couple weeks ago. After that our communication sort of stalled, and I figured he wasn't interested anymore. But then we studied together for an exam, and I think it went well. He texted me a bit afterwards. Now, however, our conversation is short again, and it seems we're about on square one again.

I'm not looking for a relationship right now, but I do want to get to know him more and be friends. I think he would be fine with that, but I'm wondering if that would not be the right approach. (I am somewhat interested, but am not actively seeking a relationship. I would prefer to get to know him more casually before dating anymore.)

Part of the issue I think is that he's really busy, and I'm really shy. So I haven't initiated anything with him. It all comes from him. So he doesn't have the time to constantly try to do things with me or talk to me frequently, which I usually rely on to become friends with people. I'm guessing he might think that I'm not interested at all.

I know this seems a bit confusing and unorganized (which it is) but I'm basically just trying to figure out how to maintain a relationship with this guy who I might want to go out with again, but I'm also not sure if he's still interested. He may have given up on me by now.

I was thinking of getting some people to go see a movie and inviting him along. Do you think that's a good idea?

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    It might be useful to know that there's a good chance that the reason conversation in texting seems to taper off could be that the other person feels they are 'carrying the conversation' all the time. If someone only responds to my questions but never asks anything in return, this makes me feel like they aren't really interested in the conversation. If you have a close friend you feel you can trust with it, have them take a look at the message history so they can tell you how you're coming across.
    – Cronax
    Commented Sep 28, 2017 at 11:28

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Being shy is hard; a lot of people interpret that as being indifferent or rude when you're really not. Unless he's got women throwing themselves at him, he's probably just as curious and nervous as you are. he's also initiated, which shows a possible level of interest.

If I were to go back to dating again, my procedure would be this: develop a rapport with someone I'm interested in. Even speaking occasionally would count here - just to get a feel for how they talk to me. Do they smile when i talk to them? Encourage the conversation? Ask me questions? Joke around? Or is it more me trying to force a conversation?

If that seems positive, then my next step would be to find something I like doing that is going on. Movies, IMHO, are kind of impersonal for a first time together - there you sit in a dark room, being quiet. Blah. Rather I'd find an event I'm going to and talk about it with her. "hey, there's an exhibit opening at ..." "The museum has a cool display of mammoths..." "I'm going to the range..." Something like that. Then, if she sounds even somewhat interested, I'd add "I'm going to go there Saturday; it looks like fun" and see the response. Are they interested in going too? Do they give any kind of response? If so, then we can meet there and actually talk to one another and spend time together doing something we enjoy. Afterward we can have a pop or something together and continue enjoying each other's company. And if it flops, at least I got to do something I thought was fun.

The same can work for you. You're not asking him out; you're meeting to do something you both find interesting. That takes a lot of pressure off and after you do one or two things you find fun, then you can talk about a date.

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  • Thank you for this. Yeah, our first date was a college activity and drinks afterward; really fun and casual. And we've been talking since. Nothing is really coming up that I can think of, so I figured a group going to see a movie would be a nice "hey I still want to spend time with you, but not in a personal date environment"
    – W.Richardson
    Commented Sep 27, 2017 at 21:17
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I was thinking of getting some people to go see a movie and inviting him along. Do you think that's a good idea?

This sounds like a lovely plan to me. Group outings give opportunity to get to know someone, see him interact with others, and lessens any date-anxiety you may have. Best-case, you can sit next to or across from him when y'all go out for snacks or whatnot after the movie...

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