I have a (clean, safe for work) photo of a pretty young* blonde woman. She and a friend were selling pictures of themselves at the last Dorian's** to raise money for a cat charity. I think in conventional terms, probably prettier than this woman (NSFW), who happens to be a bit more to my taste because I like the black hair, somewhat darker skin, and the shape of her nose.
I chatted with both young ladies a while, they seemed happy to chat. They introduced themselves, and asked if they'd see me at other Dorian's. I asked the young lady to hold onto the photo, which is 8-1/2" x 11", until she was leaving, as I found it awkward to carry around. Later in the evening she came and found me as they were starting to pack their table, and said she wanted to be sure I got the pictures, and touched me on the arm and chest a few times while talking to me. She strongly gave me the impression that she considered me attractive, which as usual surprises me in such a pretty woman.
After admiring the picture of the black-haired girl (wishing she were more my age and that Mjukhet had more pictures near my age), I turned to get up, thinking there was no way someone who looked like that would be interested, and saw the picture of the blonde girl, and realized I was probably selling myself short again. And this would carry over into any social interaction. If I were to meet a woman my age who looked like the black-haired girl would, I would probably be especially reserved, eager not to show the hubris of thinking she might be interested, and I would come across as very cold and uninterested myself. I've noticed that I often encounter that kind of reserve in women I approach, and that the women who more approach me are much more attractive in conventional terms than the ones I approach; so I think I'm seeing the same phenomenon.
I know a couple that are a considerable mismatch in terms of looks; the husband, while by no means ugly, doesn't exactly stand out; the wife is quite beautiful (especially to my tastes, long black hair and olive skin). One time the subject of preferences came up, and I related mine, and she sighed and said to her husband (in a somewhat joking way), "I'm every man's dream except yours." I don't remember his tastes except that he likes blondes. I think that one of the reasons they ended up together was that he was the guy who was not intimidated by her looks, because they don't work so well for him.
So, I'm thinking not just league thinking but even our individual tastes sometimes sabotage us, entirely unnecessarily.
* My friends tell me I look about 32, not my actual age of 42. Women who approach me are usually in their early 20s; that's too much of an age gap for me, thinking of marriage. Not sure what to do about that.
** Yes that's where I get most of my blog fodder, also the highlight of my social life.