Panel of Experts

I feel like I need a panel of experts with me at all times to help me get back into the dating pool. Not that I was ever a confidant social swimmer, but I really feel like I should be asking people advice this time. I'm still dependant on my relationship water-wings.

For instance, there's the whole personals thing. Should I spend $20 to send out an email? Is it a waste of money to send someone an email whose pictures indicate a level of gothness I might not be able to deal with? (But which I also find masochistically attractive.) Should I just stick to the free, but for some reason (at least it seems to me) more risky craigslist.org personals? Should I try to meet real people face to face like a normal human being?

Also, there's this girl who works at the Subway near the depot, out of which my mattress delivering is based. We kind of smiled at each other the first week. Never said anything more than what I wanted on my sandwich, and I ate there every day. (Not actually because of her, just because I like subway and am boring.) So week number 2 rolls around, and I go in for my daily sandwich, and she has her hair all done up and she's wearing waaaay too much makeup, and she keeps walking out from behind the counter to do things like put 4 ice cubes in an otherwise empty cup, and smiling at me. What does this mean? Does she want me to ask for her number? Does it mean she has a photo shoot after work and is working on a recipe that requires exactly 4 frozen blocks of water?

I also need someone to help me not say stupid stuff, and to compliment more effectively and often. When I first started going out with Kristin, I regaled her with a tale about me throwing up with such force in the toilet that a little bit got in my eye. That's not a good story to tell a prospective girlfriend. It's a wonder she stuck it out as long as she did. And saying things like, "Hey cute pants" don't convey that I think the person is cute. It conveys that I think their pants are cute, which generally I don't. I don't know cute pants from non-cute pants, I just know that someone looks nice. What I need to say is, "you look nice." But phrases like that are much to advanced and sensible for me.

All this is to say that I don't want to keep my cycle of 2-3 years between girlfriends. It's not a good cycle, and I refuse to continue it. Unless I can't help it, in which I case I'll just deal.