Is Someone Playing a Joke?

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Okay here we go again...everyone knows the deal with me. Never had a girlfriend or a girl that's a friend. I have countless stories about girl after girl and how nothing ended up resulting from it and I have made it 22 years without a girl in my life. I think once I tried to kiss a girl when I was in 6th grade and got denied, and I've never had an opportunity since.

Is it because of me? Somewhat. Is it bad luck? Yes in some cases.

Is it because of a lack of trying???

After the last couple of failures, I was sick of it. I have been trying for 5 years now and have gone through my senior year of HS, community college, and then a bigger 4-year college. I can deal with failure once, twice, thrice....but after hearing story after story of how crazy things would happen, how the odds didn't go in my favor, I figured I would stop trying and hope that one day it came to me.

So at work, I'm in a big building so I walk around and a lot of people from other offices do as well. Walking down there gives me hope that I will run into someone special that's around my age and while I have seen some girls I would like to talk to, the situation hasn't presented itself (meaning im not going to cut across the hall and approach someone bc that would prob be creepy)

But what happens...a 40-something year old lady starts flirting with me...following me around, and trying to send cues to have lunch with her. Then I was in line one day getting lunch and there was this kid around my age that noticed my Yankees shirt and because he was a fan himself we began talking. So we sit down to eat and were getting to know each other, talking about sports, etc...and then towards the end he asks me out.

Yes I said that right.

I'm not gay but I don't have any issues with them but I just thought it was crazy how the whole thing happened so quick.

Now I guess the one positive would be that I was appealing to someone, but what gives.

If only I would get an opportunity like that with a girl my age, I would be golden...but why don't I appeal to my desire? I don't know it's just laughable to me. I have all these crazy things happen to me trying to get with a double-digit amount of different girls and then I score...with a cougar and a gay guy.

It feel like someone is playing a joke on me? Anyone have any idea what I can do? Thanks

Typically this is the result of our inability to read emotions, and pick up on body language. I've had gay men ask me for a date, and I had no clue ! !! You probably need a male NT friend to help you with this skill, most of them are downright predatory towards women.

As for the older woman, don't be so quick to say no ! ! You should give her a chance and see what happens ….

I don't know, I just don't get it...every time I seemed to have something brewing with someone (maybe 2 or 3 of the 10+ girls) something was in the way, either a boyfriend or an engagement ring. The others it just would never get to that point.

And as for the older lady in her 40's...I can't really see myself doing that. I feel like I would just be using her because in my heart I know it would never be someone I would realistically be with 5 years down the road.

Thanks for your comments, I appreciate it

Well yeah I tried to take positives out of it...unfortunately it wasn't a funny story because the gay guy kind of felt like a fool and looked like he was about to cry, got up, said "sorry to bother you," and left.

All I said was "Sorry I'm not gay" and I don't know if he felt foolish because he asked right away after just meeting me. I felt bad for the guy, I would of been friends with him but he just left ASAP.

Well, maybe you can try to clarify if you see him again.

Perhaps it was your tone? Who knows. If you didn't have a negative tone, maybe he was just upset he was rejected, although it might be a good thing he left.

If he reacts like that over you telling him you're not gay, maybe he'd be quite the dramatic friend. I wouldn't bother with someone like that. I don't like drama.

Nah I was just like "Sorry I'm not gay." Just a regular tone...but anyway back to my actually issue...what is it?

Why am I attracting the wrong species?

Hit and quit the 40 year old woman for some confidence.

You'll figure it out as you get older (the rules of the dating game). The more experiences you have, the more you are able to make connections in your brain. I don't think you are unattractive. I think you just don't understand how to get from point A to point B. I don't know about you, but I shut down when I don't know what to do in social situations. I am kind of like Raj from the Big Bang Theory when I am face-to-face with a woman and there is mutual attraction (or just me being attracted to her). If that is how you are (lacking self-confidence) perhaps you can talk about specific scenarios with an understanding friend. I suggest talking to females instead of males.