I really want to be with him, or be his friend, but worry he might not want to even talk to me

A female age 36-40, anonymous writes:

My cruch and I went to high school together and we were pretty good friends then. I didn't get to talk to him as much as I wanted to though because his girlfriend saw to that, who I was friends with. He and I were also really shy around each other but still tried to talk from time to time. Later, he started going out with another one of my friends who knew I liked him. I don't think he knew about my feelings though at the time. And she used to tell me about things they did together and it really bothered me. But they eventually broke up as well. Anyway, around our senior year, he didn't have a girlfriend and I was still single. So around the time of senior prom, he started talking to me more, asking me about my day, and gave me a phone call every once in a while. Even though we didn't talk much on the phone, I was still glad he called. Soon, during the baseball season, we sat next to each other on the bus holding hands and small stuff like that. So, eventually, he asked me to prom so of course I said yes. Then he asked "are you sure?" and I said of course I am. So we went to prom and held hands a lot through the night when we were together, but he also spent a lot of time with his friends too. About a week later, I asked him if he wanted to go out with me, and he said "we'll talk about it later". So I thought he would call me later or something. But he didn't really give me an answer, so I asked his best friend what he thought about me. And he said "he really likes you!" So I gave him time because I know that he was living in a foster home so I didn't want to add any extra stress. So we eventually lost touch and haven't seen each other in a while. And about a year later he called me asking me "did I want to go out?" So I said "yeah". We didn't talk for a few weeks and I asked him "you don't really want to go out do you?" so he said that he didn't mean going out as in a couple, he wanted to just hang out. So it hurt me some and we stopped talking for a while again. So around last year I started working at one his usual hang-out spots. And almost every time I looked at him he was looking at me. He made sure he didn’t go through the night without at least saying hi. And there were times it seemed like he was just staring at me. I eventually had to quit that job so it’s been almost a year since I seen him or talked to him. I think about him a lot, and there are times that I really worry about him. I really want to be with him or at least be friends, but I'm afraid he won't want to talk to me after all this time. What should I do?

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A male reader, CaringGuy  +, writes (14 January 2010):

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