ohmanthatscrazy

I've never been good at this because I am normally a shy person.

In junior high I had a major crush on a guy, and it extended into the first couple years of high school. We knew each other but weren't really friends, and he knew I liked him even though he never directly told me I didn't have a chance with him. During the last couple years of high school and my first year of college I basically 'moved on' and explored opportunities with other guys. Recently I had the opportunity to hang out with him in a group of people but I didn't talk to him much. I'm sort of playing with the idea of trying to pursue something with him but I'm sort of unaware of how to go about it. I have his screen name on instant messenger and I've talked to him a couple of times since I saw him, and it didn't seem like he was that opposed to me.

But we have an awkward past and I don't want him to think I've been obsessed with him for the past almost 6 years, so how do you think I should go about it?

Tina Lee

If you hang around, and make yourself seen, then he may pursue you. Be yourself. As I said, hang around with your group of friends, but I wouldn't say anything just yet.

You said that he knew years ago that you liked him. Is he shy? Maybe that's why he never made a move on you?

ohmanthatscrazy

Well we don't really have the same circle of friends, I kinda had to go out of my way to create a situation where we could hang out. Luckily his good friend liked one of my friends. But that's not going to happen again because my friend doesn't like his, so now I have to go out on my own.

Honestly I can't tell if he's shy or not. It somewhat seems that way but somewhat doesn't. His last three girlfriends were in the same group of friends, so I don't imagine he really goes out of his way to pursue girls.

Tina Lee

That's what I had thought. You kinda have to be right under his nose, for him to make his move.

When you guys are talking, is it a friendly chat, or does he flirt with you?

ohmanthatscrazy

We hung out with my friend and his twice and he didn't really make an effort to talk to me. It sort of seems like he's the type of person who speaks when spoken to--just like me. But he knew I was going to be there beforehand both times and went along.

Honestly I think it's just friendly chat. I throw in my sarcastic sense of humor sometimes and he reciprocates, but both conversations were less than ten minutes and mostly about school.

Tina Lee

Yeah, I'm afraid it does sound like just friendly chat.

But just stay carefree & aloof. When you guys cross paths, chat with him a bit and see if he gets more confidence. Maybe he's just really shy, or maybe he's got his heart set on another girl, I don't know.

But I"d hate to see you make a bold move, and then find out he's got other plans..

Good luck though. I hope it's a happy ending for you!

ohmanthatscrazy

Well I'm pretty sure if I don't do something that's not gonna happen. Honestly at this point I'd actually like to get it over with. If I don't have a chance with him I want to know now so I don't always go back to wondering if I may have a chance with him. That's why I'm asking what I should say to move things along.

I don't want to wait and wonder if he's a possibility anymore, I want to know now.

Tina Lee

I can understand that too..

Why don't you mention that when you were in school, "remember when I had the crush on you?" That might start the conversation.

And then at that point, depending on what signal you're getting --you can then choose to let it go, or pursue it further.. It's a statement about the past, but isn't admitting anything in the present, until you're ready to.

ohmanthatscrazy

That's actually a pretty good idea, I just don't know if I'd have the courage to do that.