Hopeful, but confused

[kooooo8]

Hello Everyone,

Um I'm in a bit of dilemma. A bit of back story, i've been talking with this guy on OkCupid. We share a good amount of interests, personalities that are similar, on friendly terms. There was a period where he went though some very hard times, and during that time he stopped talking to me. A couple months later he came back apologizing, and I attempted to just pretend nothing happened. He explained to me the troubles, and I thought we made a good milestone in our friendship considering how we live in different states yet he is comfortable enough to share with me what is happening.

Fast forward, we stopped talking on OkCupid and are now talking via messenger apps. I've had some good long conversations with him, and I do genuinely like him. So my dilemma is I don't know how I should approach our friendship. I want to date him or at least propose to date him after a few meetings. I'm kinda old fashioned in that sense. This is the first gay guy i've felt this way about, and I feel like i'm in high school again ready to hide in a corner, or too scared to talk to him about it. I don't want to seem too forward with him considering he is pretty introverted like me.

[Bowyn Aerrow]

IF you are able to talk about his problems, then why can't you talk about this?

Why not tell him exactly what you said here?

I want to date him or at least propose to date him after a few meetings. I'm kinda old fashioned in that sense. This is the first gay guy i've felt this way about, and I feel like i'm in high school again ready to hide in a corner, or too scared to talk to him about it. I don't want to seem too forward with him considering he is pretty introverted like me.

But do change it slightly to something like:

You are the first guy I've felt this way about, and I feel like I'm in high school again ready to hide in a corner, or too scared to talk to you about it. I don't want to seem too forward with you considering you're pretty introverted like me. I want to date you or at least propose to date you after a few meetings. I'm kinda old fashioned in that sense.

If you want you can just copy and paste the above....

I think this says what you are feeling, and brings up the issue and explains why you are slightly reluctant to even talk about it.

The worst that can happen is that he rejects you... However rejection in this case is better than pursuing it in 'hope' of more without that hope bearing fruit.

[LateBloomer]

You think YOU'RE old fashioned?

Wait until you here THIS.

You live in San Diego, apparently. Why don't you get out of the house and go meet someone in person and talk to them face to face?

I'm sorry, but communication by texting is EXTREMELY limited. It's limited to such an extent (and I don't care how many smilies you use) that there is NO WAY you can get a FEEL for the real person behind the electronic device.

Get this: He might not even be who he says he is!
Think about that for a second.

Listen, I like technology. I met my current partner online. We skype and text and use Facebook. The whole Nine Yards.

You live in a big city with a vibrant gay population. Go live life.
Good luck.