Why do men choose to marry a plain Jane woman over a pretty woman?

Older men? No way to tell, really. What they thought was attractive was something even experienced hookers had no clue unless they were a repeat customer. It was really rather astonishing. Oh, there were a few weird exceptions. Old guys loved Cher. (Her working name.) If they used a walker, we called for her. No idea why. Oh, she wasn't hard on the eyes, but had been in the business for quite a while.

Two things, both primarily from my experience working as a bartender in a brothel and seeing the most extreme version of this first hand. You see there, when a guy comes in looking for a ‘date’ the only thing they really have to go on is looks.

About the only things that seem to be at all consistent are ‘healthy’ and ‘clean’. Otherwise, well,

Being fat is a trap - Hacker News

Young men chase ‘pretty’ women. Under 25, they would pick the ‘Barbie doll’ almost guaranteed. Blond hair, tits, smile, pretty. She was. And they'd get what they picked, if they had the money.

Men like what they like, and it rarely follows much of a pattern once they get past the initial ‘if it has boobs and hair’ phase of development. Gay men are a little more predictable, kinda sorta, but not really. Once they move past the ‘back alley upright’ phase of fucking anything they really do diverge a lot in tastes.