Well, my first attempt at trying to move on went pretty horribly. Had the second worst date ever so far.
So I meet up with this cougar from OKCupid (she was 38). When we were chatting online she was quick to respond and seemed pretty friendly for the most part, and she seemed eager to meet up right away. So we decided to meet for coffee. Immediately I realized that there might be problems with this one, since she tried to shake my hand, and when I tried to hug her she seemed visibly uncomfortable. Then she didn't want me to pay for her coffee and said we should have separate bills. Sure that in itself probably might not have meant anything negative, but it didn't seem good. The first ten minutes we sat down and she kept having this weird, nervous look on her face. However, after that she started feeling more comfortable and she was smiling and seemingly actually enjoying herself. We chatted for two hours and I asked if she'd be up for something else. She said she was, and so we went to theater, which at first I thought was a good sign. Again, though she decided to pay for herself and when we went inside, she didn't seem to want to hold hands or anything. The movie experience (as well as the movie itself) sucked and was glad when it was over. I walk her to her car and ask her if she wanted to pursue a relationship and she says that she's not looking for a boyfriend right now and wants to remain friends.
UGH.
Okay, so she wasn't exactly the date from hell, and it's not like all my other dates ended in a slam dunk. But most of the time I had SOMETHING to show for it. This wouldn't be so bad if I didn't waste half my day with her.
At least she paid for her own shit, so credit where credit's due, I suppose.