My friends met Larry David and I didn't

I generally have two groups of friends that rarely hang out together. Both are from Wisconsin, but different groups. Kumar's in one, while a guy named Bob is in another. I worked at a WI bar with Bob, so a lot of us meet up. On Saturday, each group was going to a different beach. Since Bob asked first, I went with him to North Ave. Beach. As expected, it was a good time, and now I'm really burnt. I met the boyfriend of one of the girls at the beach. He was a nice guy, but not as attractive as the girl (typical). So overall, our beachtime (and 44th floor rooftop swimming pool) was a good time.

Meanwhile, Kumar, Jay, and some other people went to a different beach. As I found out later, they ended up meeting Larry David on the street. Apparently he's pretty awesome, and now I'm jealous.

This weekend's nightlife wasn't filled with too much. Just dive bars and dance parties. As far as meeting girls goes, there isn't much of a story. I chatted up a skinny white girl who was wearing a Nas t shirt, but that's about it.

Last week I watched the movie Yes Man w/ Jim Carrey and Zooey Deschanel. It wasn't really good or anything, but generally entertaining and Zooey was cute as usual. It gave a pretty good general message to do what you want if you're the only one stopping yourself. I'll try to apply this to the whole thing I have with girls now. I guess if I'm pretty drunk at a bar it's not so tough to talk to someone, but I'm still a little hesitant about random places. I saw a cute girl at the grocery store today, but never said anything because it felt like I was ambushing her or something. Maybe none of it matters, though.

While I was at the beach with Bob and three girls who I've met once before, I tried to work on my conversation skills. I felt less pressure with them because they all had boyfriends, so it's not like I was trying to be smooth or anything. Since I had already met them, I also didn't have to be afraid to say anything introductory. I still had the problem of not knowing what to say as part of conversation. Would I proceed with more "getting to know you" questions? Or should I just say random things to them as I had to Bob? Keep in mind, I think I had already told about 5 horrible/boring stories to him that day, so it's not like I was keeping those gems for close friends.

Is that how it works, though? Don't try to "turn on the charm" and instead just talk to girls like you've been friends for years? And then just pick from whoever likes your conversation? or instead do you "be yourself" but just focus on not being really boring?