Is this a American cultural quirk I'm not understanding? Who cares that he's old enough to be her father? Why is it interesting or relevant? He married an attractive younger woman. She married a rich older man. It happens every day all over the world. Its not the first marriage for either of them and they both already have children. It says very little about either person involved except that one likes attractive women and the other likes rich men with a sense of humor (if we assume the most cynical motivations).
> Is this a American cultural quirk I'm not understanding?
As an American I would say: yes, it is.
I suspect it has something to do with the rising neoteny of more recent generations coupled with America's persistent puritanical views on sex, but there has been an increasingly bizarre fixation on the age gap of couples. All teenagers have recently be re-defined as children, so much that it's common on places like reddit to view even attraction to say a 17 year old viewed as a form of pedophilia.
For nearly all of human history men over 30 forming relationships with women in their late teens has been normal. This was even not too rare 30 or so years ago in the US. But there has been a rising moral panic about age and sex that leads to comments like the above.