If I was the man I am now when I was in my late 20's my world would be rockin. I have broken the wall of shyness, style and self confidence but here is where I TOTALLY get blocked (well this block and simply that I dont feel I have built up enough experience to be comfortable 'settling down' YET but its starting to roll).
I am 44.
But to be honest a George Clooney kind of 44 (just as a random reference). I was dating a woman who was 51 who broke up with me because she said 'you need to date younger women and you are the kind of guy who can pull that off and until you get that out of your system you cant have a relationship'. Well the thing is when she said that it was TOTALLY what I was thinking that entire week before she said it.
Bars and nightclubs are often filled with women in their 20s, additionally to be honest I like going where they go so I am exposed to them but when I see an attractive woman the first thing I do is size up their age and that that millisecond is just enough for me to say to myself 'i bet she is too young'. I totally need to break that. Me being too old for her is her choice, not mine at the moment and besides I need to be able to brush off that kind of rejection. In fact, a little rejection could do me some good because I would learn to not worry about it.
Understand I am not looking specifically for a younger woman and its not even on my to-do list, its just that there are a lot more attractive women looking who are younger then attractive women who are older and looking.