Everyone so far has given me some really good advice, but I was told that a few more specific examples could help more. Here's a few selections of situations I've found myself in. These were all solo attempts.

  1. I get shut down right from the get go. I made my approach, stood next to her at the bar ordered my drink and then I introduced myself. The girl says hi, and then turns her back on me. Now I didn't bother trying any further with her, but it did ruin my mood.

  2. This time I initiated and things were going great. I complimented her, gave her a few neg's, and just had her hooked right away. There were lots of IOI, and she kept wanting to know more. I told her something that freaked her out (oh hind sight) and it was game over. I've learned from that, but now I think it has me self conscience and worried I'm going to freak other people out, which leads me feeling like I've run out of "safe" topics.

I don't do small talk well, I get bored easily, and my idea of funny or entertaining seems to be radically different from those around me.

Edit 1: Thanks, lots of good advice, and it's made me realize that I've been sitting out way too long. Time to get out and practice. Sorry if these are specific enough, but those were the last ones I could remember well (those nights I didn't end up in a drunken stupor) Thanks again guys.