Hey guys, I think I have a unique problem.
For one let me start off with the fact that I am a young adult (black) male and interested almost exclusively in (generally white), older men. I am not trolling. When I say older I mean generally 50+, I have gone for 40s before, 60s is great too, 70s is kind of pushing it but still sometimes hittable. I know that sounds gross and to a normal person it probably is. However in my head it's just very hot.
That said, I have yet to have any type of relationship of any kind with such a man that wasn't first arranged on a dating site. Makes sense, right? The nature of the attraction doesn't make ordinary methods such as merely approaching an attractive man viable, for reasons you can imagine. So it's always been online.
But a few years ago I met a guy who I found attractive and strangely I also got the feeling that he was attracted to me. I was very cautious with such thoughts, really, because I knew it could just be the lonely side of me reading into things. He and I had a semi-business relationship where I was sort of his intern.
This happened during the final weeks of my senior year in high school. For two weeks my class shadowed someone who worked in a field of our choice; presumably someone in an industry we'd like to be involved in in the future. So I worked for him, but it was really rather casual and nothing too serious. I was kind of his friend even afterward, helping him and his daughter with a few projects and even got paid a little bit. However eventually we fell out of contact and I simply didn't talk to him for a few years.
At the time it was merely an unrequited crush I had. To try to avoid any kind of disappointment or heartbreak I considered the facts. He was very Catholic. He had a daughter. He was almost sixty. He was an old white dude and I was young black guy. I'm not sure as to his marriage status. (If he ever had a wife she is no longer around, I don't know if she's dead or divorced or something, but I've never heard anything of her from him or his daughter.) So these factors mounting up it seemed pretty unlikely that he would actually like me -- despite the impression I got the first time I met him. I mean, statistically, my attraction is probably pretty rare, and similarly for him to be attracted to me seems unlikely from a statistical standpoint alone. Not to mention other considerations like him liking my personality or body type and shit like that.
However there was always some part of me that thought otherwise. The look he gave me when we first met strongly reminded me of the gazes I had gotten from other dates who liked me. I can't think of any other reason why someone would stare at me for several seconds mid-conversation with just a sincere smile on their face if it wasn't admiration or something else.
It was a few weeks ago when I saw him again for the first time in a while. This time I was trying to be much more attentive toward "hints". My experience in the mean time had taught me that the things I pick up as hints often are. And, well, he dropped what could be looked at as several hints. When he saw me he looked very happy and told me I looked good. During that same meeting he made a few other compliments. At one point he was singing to me, "Look at that face" by Barbra Streisand:
Look at that face just look at it!
Look at that fabulous face of yours,
I knew first look I took at it,
This was the face that the world adores,
OK, what?
Well I guess this could be a gesture of friendship or it could be him hitting on me. So there's the intuitive part of me thinking, this guy wants me. The logical part of me goes, pfffft how could that happen?