I suck at this.

I keep forcing myself to go out, especially with groups of people that I know to be pretty lively, in hopes of getting to meet someone and that. Hasn't happened. Actually, that's a lie, last night at the bar some 40-something cougar jumped into whatever our conversation was about (I was kinda on the 'outside' of the group, making this easy), plopped herself right beside me, arm around me, and started talking about something. I didn't brush her off or anything, but I was pretty weirded out by the experience (not exactly common for me, especially because I hadn't even noticed her until that point) and I didn't really keep things going with her, so she left shortly thereafter. Perhaps I look older when I've got some stubble? Or perhaps she's just a cradle-robber. Whatever. The point remains that I suck at this. I still can't get myself to open.

I can come up with excellent "routines" though. I was thinking about hitting up the mall today, and in my mind came up with a great way to get in with some women.

Me:"Hey there, can I ask your opinion on something? Do I look gay?"
Her: yes/no/whatever - doesn't really matter
Me: "See all my friends keep telling me I dress like I'm gay, so I came here to get some new clothes. What would be a good place for a guy like me to get not-gay clothes?"

The idea is to get them to walk me to whatever store they suggest (I can use my recent arrival to the city as an excuse for not having any clue where anything is in the mall), and transition into getting them to shop with me, tell me what looks gay, etc. The stars have to align for the conversation to go exactly that way, because their responses have a lot to do with where it goes; but the point is the journey, not the destination.

I can swear up and down that that's what I'm gonna do, but I won't actually do it. I already know that.

All I need is the ice-breaker. But a big ice-breaker. Just the original opener isn't just what I need; but I need to get to the "they kinda know me, know my name, etc" acquaintance type stage. Once I'm there, getting wherever I want to go with them is easy. Getting there is the hard part. And I just can't do it. I don't even really know why.