Let He Who Is Without (Redux)

Warning: The following post is not recommended for recovering judgaholics. 

I know, the heart wants what it wants. Still, I wonder what some of you think - when you're not in a kind mood - when you see two people romantically involved who ...
* By any objective (OK, subjective) standard are just not in the same league in terms of attractiveness and ...
* Are widely disparate in age, like say, at least one full generational cohort apart and ...
* One of the two is very wealthy or very in the public eye or both and the other is neither.

I understand the impulse to get romantically involved when both people are very wealthy or very in the public eye or both. What befuddles me - again, in only my unkind moments (and no doubt I have these much more than any of the more evolved folks reading this) - is what exactly draws people like this together? So, let me pose my judging question in the kindest way I can for anyone brave enough to admit they've shared my befuddlement, but not my judging component, of course.

Imagine you've just seen one of these pairings on TV or in the newspaper and you're not feeling very kind. Which befuddles you more? The delusional vanity of the much older, either very wealthy or very much in the public eye (or both) but not terribly attractive person? Or ... the calculating avarice and/or sycophancy of the much younger, neither wealthy nor in the public eye, stunningly attractive person?

Forgive me Father for I have sinned.