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As you and redsky mentioned having fun, I recall trying that. One of my problems (I think) was the company I was with. Back before I got married, I hung out with a group of guys who didn't follow any of this PUA advice. From what I could tell, they were just standing around in the club with beers in their hands, staring at everyone. So when I was trying to have fun, I believe (based on what you just wrote) I just wound up making myself look like "the entertainer". Of course, I'm sure there is probably methods I could have applied to counter that, but I wasn't and still not that advanced. Other than that, only thing I can think of is to get a different group of friends to go out with, but that's easier said than done so that's why I hope to be able to get comfortable going out alone.
What is The Natural Method and where can I find it? I feel that's a bit more in tune with what I need. I'm pretty good with women when I have them in my web, the problem I have is luring them to it. I know I could stand to lose a couple of pounds (I suppose I'm skinny-fat) which could help drawing an initial look from women because a lot of times, I feel they just glance right past me. However, I realize even the most blah-looking guy can pull a hot chick. That's kinda why I came up with this thread, I want to learn how to feel like I belong, no matter what the environment is so that I can eventually draw attention and work up the nerve and approach random women.
The Natural:
http://www.amazon.com/The-Natural-Effor ... 0062089781
The problem you had with your friends is they were boring and were too busy trying to look cool for everyone else that they wouldn't open up and have fun. It's not your fault, it's theirs. Besides, I find it best to go out with one friend. Groups generally don't work if you're trying to get women as it's more focused on the interaction between the group. So you have a lot of the same bullshit talk about football or other sports going on and not much fun or freedom to do what you want being part of a group. The only benefit to group outings is when there's a bunch of women involved or you're not afraid to leave the group and use them as a base from which you go to and from, making new friends and talking to random women.
Go out one of the nights with a good friend or even someone you hardly know, have a few drinks, go to a club and just have a laugh. You'd be surprised how much fun and how much freedom you'll have with just one person not to mention how good friends you'll become. Get used to this and then head out with them picking up women.