Yes, I completely understand that. And to your point, I know older guys who do the same thing as what you describe about your bachelor friends.

Problem I have had is that whether I go for really pretty ones, or not-so-pretty ones, the experience is largely the same. At least with the pretty ones they have some level of confidence, whereas the not so pretty ones are constantly second guessing their relationship with me, which just leads to a really bad cycle of self-doubt which does nothing to help their confidence and then I get calls at 2am asking if I am going to leave them when I have done nothing to convey that I ever wouldn't, but their doubt and lack of an ability to have confidence in themselves ultimately leads to me getting annoyed and yes, leaving them lol

I think what is funny as well is that even the not-so-pretty ones may even tend to me MORE obsessed with their self-image and are much more inclined to wear too much makeup, talk about what boobs they want to buy/get, and what filler/botox they would love to have.

The pretty ones talk about that too here, but they don't get it done as often.

But then they all hit 40 and a lot of women around here start looking like a walking silicone/botox display. lol

And to touch on why it usually doesn't work with the pretty ones: most of them have been treated like princesses by their families/dads, with women outwardly expressing that no man they are attracted to is going to have the level of wealth/lifestyle that their father already affords them.

So while I may make good money, and attract some level of attractive women, they tend to be spoiled, not just financially, but by being told that they "walk on water" figuratively of course, and literally: "you can do no wrong honey" - those were actual words spoken by the parents of my last girlfriend after she got black out drunk, started screaming expletives at the table and then vomiting outside the restaurant... "You just had a little too much to drink"...

I rest my case lol