I think this post resonated with a lot of people, myself included. It's something I think about a lot, even though I understand there is no point thinking about it or dwelling it.
I got no action in my university years. Objectively I'm a lot happier now but at the same time I know I'm far from young anymore and that really grates. I also hate that I'm too old to get the young girls (at 36 I think realistically the youngest girls I would get are 26 but more often late twenties or early thirties).
The problem is my mindset now is the mindset all the people having fun seemed to have in college, i.e. drinking, partying and getting laid. Whereas when I was actually in college I didn't drink and was too shy and awkward to really enjoy it. They weren't happy times but, as some people have said, I tend to look back with rose tinted spectacles, for a time that never existed. It's a common phenomenon though, people will be nostalgic for an imagined age. The film 'Midnight in Paris' is sort of about that, amongst other things.
Describing the feeling as a 'void that can never be filled' seems exaclty right. I just can't bring myself to settle down now, whereas the guys who were players in school and at college are almost all now settled down. I don't know if they are but I always imagine them to be happy because they were successful in their youth and therefore have nothing left to prove. Whereas I feel that I do. It's not that simple of course, I do love meeting new women, variety, etc but part of it is trying to make up for lost time.
It's hard to deal with. I do understand that it's better just to move forward but for us introspective types it can be tough.
I hate the fact there's such a disconnect between the mindset of the girls I date now and my own mindset. I want fun and casual flings, they want marriage and kids. I'm kind of horrified to see that my friends are now married and having their second or third child. It shows me that there's nobody around to party with. I think if I had buddies that were single and were up for trips to NY or Vegas to swoop women, I would feel ok. I have money now, I can afford to go anywhere, stay in nice places, eat at great restaurants, etc. My life is much better now than it was but I don't have people to do that stuff with! Everybody has settled down. I don't get it, I really don't. That wife and kids lifestyle sucks for me. I can understand some people choosing it but EVERYBODY I know has gone down that path.
I wish I could just meet some like minded guys to get up to shenanigans with. There are clearly a lot of people like that on this board but most of us are scattered around. It's a shame. A lot of the times I resort to rolling solo. It's ace sometimes but other times it's kind of isolating and I see these mixed groups of young people drinking, having a good time and probably screwing each other and I do feel envious and like an outsider.
Everybody is so serious now. Everybody is preoccupied with their kids. I don't feel the same urge to settle down and have kids at all. What are you supposed to do in that situation? Having said all that, right now I would rather have my life than theirs (the guys who got tail in college but have now settled down I mean). They may be very content but it's just not for me, so right at this point I'm happy I'm still single, travelling to different countries on a momen's notice and meeting new girls (I'd like to meet many more but I guess I have to get better).
Sorry, maybe some of this post was off topic but the OP and subsequent discussion definitely hit a nerve. It's something I, and by the sound of it many others, have been thinking about a lot but I didn't realise a lot of other people felt this way. I just want to hang out with buddies, drink and screw a cornucopia of women, you know? I dont give a f**k about catchment areas for schools, house prices, climbing the corporate ladder, etc. But everybody around me is, so I feel really isolated.