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What kind of girl should I pursue? (if any)


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Posted (edited)

I'm a quiet, insecure guy who is slowly analyzing and working on conquering my many, many problems in terms of dating, relationships and social activity. Recently I've been thinking about the few girls I've tried (unsuccessfully) to court, and it breaks down something like this:

 

age 16/17: girl in high school who was somewhat short, brown hair, feisty personality -- awkwardly asked her to go with me to a school function and got shot down majorly. Bummed me out for over a year.

 

age 18-?: girl I met online, then talked to on the phone for years and met in person a couple times; she was 5 years younger and I was an upstanding citizen so I refused to even go to a movie with her, for fear of reprisal or doing anything illegal/immoral etc. When she was finally of-age and we finally hung out a few times, most of the time it was a disaster. She couldn't "read me" = basically my mannerisms threw her off entirely and ruined any chance of anything. This was after years of great phone conversations. She was really a bit of a head-case, I'd say we were both basically messed up and just not at all compatible in person.

 

age 18-22+: college, obsessed over girl who was 5 years older; short, dirty blonde hair, was essentially a bipolar sociopath (I was too young to comprehend that at the time). She liked me a bit at first, then I ruined it by acting awkward, not having anything to say and then by obsessing over her saying I was in love etc. Wrecked me for years.

 

I'm 35 and I still think about this last girl occasionally. She is married now (I think she is still married anyway) and has several kids. If I think about it logically, I wouldn't really want to be with her even if she wanted to. We don't have much in common, either in interests or in terms of personality. I could never trust her because of her bipolar, amoral nature. And yet, I still identify love as the time I spent crying myself to sleep every night wishing I could be with her. It's the closest thing I can identify to love anyway.

 

Strong, burning obsession is what I associate with love and I don't understand any other kind; I don't seem to have felt any other kind. Is normal love obsessive at first? Do you feel obsessed when you have an actual relationship, not just unrequited love? I don't understand how strong emotions like that can coexist with a stable actual relationship.

 

I seem to consistently chase after "exciting" girls who I imagine as or who are in fact out of my league, obsess over them and get rejected. I have actually been liked and have even obsessed over a few times myself, usually by short blonde girls who are fairly unattractive to me. I find the experience repellent and it kind of kills my interest, especially the obsession part. In my mind, if a girl likes me -- what the heck is wrong with her that she would like me? Why would anyone like me or worse yet obsess over ME? I have no self-esteem, so if someone likes me "there has to be something wrong with them."

 

So anyway, I think I got off on a tangent there. But as far as what kinds of girls to pursue -- I seem to have a tendency to be highly attracted to "exciting" girls who are really forward and outgoing and socially successful, and really nothing like me. I, who struggle to even be slightly normal socially seem to find them very compelling, but all it tends to do is end in my rejection and heartbreak. I also see a pattern in that many of these girls have similar physical features (short, pretty and ultra-feminine looks -- Zooey Deschanel is a prime example) and also unstable, possibly bipolar and aggressive.

 

I guess recently I was pretty interested in a SOMEWHAT shy, quiet girl who shared some of my nerdy interests -- but she was taken, and I think I mistook her actions toward as flirting when maybe they weren't. I actually tried testing the waters even KNOWING she was taken, but she was ultra-loyal and there was no way it was happening.

 

Anyway, advice appreciated.

Edited by ChessPieceFace
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