There seems to be a fundamental disconnect in my life. And finding the root cause has proven quite challenging.

I live in New York, and there are an abundance of beautiful women in this city. An abandoned of women with all sorts of personalities, interests, ethnicities, shapes and sizes. Yet. I seem to predominantly attract girls who are heavier. Rarely do I attract a fit girl. And when I do, there is often some other flaw making her quite undesirable.

A little bit about myself. I went to a great school and have an engaging, lucrative career which involves a lot of responsibility for my age.

I go to the gym 4-5 times per week. There are certainly men with better bodies. But I am in decent shape (no beer belly, somewhat muscular).

My looks are average. And my clothes could use improvement (better brand names perhaps for the "perceived luxury" implied by an alligator), but they are a far cry from ridiculous or embarrassing.

Most importantly, I am articulate and intelligent. A bit of an elitist who harbors some anger and resentment, sure. However, I am quite comical and congenial.

When I go to a party or an a trip. I am quickly catapulted towards the center of attention with my humor and wit. Or I am ostracized as the immature, loud and boisterous one. It is very binary and depends on the crowd.

Lastly, I put myself out there. I often talk to people in lines, elevators, café's, etc. despite the rejection by which these actions are often accompanied.

Yet, I still attract women who are certainly "below average" looking. I simply fail to understand why.

Has anyone else had a similar issue? Are there patterns or red flags I should watch for in my own behavior? Are there exercises I can do to gain a better fundamental understanding of how I am perceived by others?