It seemed like the right choice at the time

After the pool party, I started to think that there was a chance Jane liked me. One thing we talked about during our conversation at the pool party was Homecoming. Testing the waters, I said that she probably already had a date lined up for the Homecoming Dance. Surprisingly, she said she didn't. How much I wanted to ask her to that dance! How much I wanted to ask her then and there, in front of everyone! How much I wanted her to reply, "I was hoping you'd ask me that, now kiss me you fool!" How much I wish these excessive exclamation points were not formed out of exasperation.

I decided not to ask Jane to Homecoming. It really did seem like the right choice at the time. Here was my thought process.
1: We just went to Spring Fling. Although that was about 5-6 months earlier, there was only one other dance in between, so it would be pretty close. I didn't want Jane to be frightened by my forwardness in asking her to two dances in such a short time span.
2: For the past couple years, I really wanted to take Jane to prom, and this year would be my final shot at it. Similarly to reason #1, if I asked her to Homecoming AND Prom, that would be too forward and I would certainly scare her off.
3: I'm probably just imagining this stuff about her "maybe possibly sort of liking me" anyway.
Here's what I wasn't thinking.
1: If you are already entertaining the foolish hope that she likes you, and it turns out to be true, then she probably wouldn't mind that you asked her to several dances.
2: If for some reason she really does like you, how do you intend to keep her interested while waiting for Prom.
3: Asking her to Prom will be beastly-hard, because many guys will be thinking the same thing.

Generally when I chat on MSN Messenger, the conversations are fairly mundane. However, over the years I've had a few conversations that really shaped my world. Jane's good friend Whitlie graciously provided me with such a conversation about a week before Homecoming. The conversation was short, and the relevant part was even shorter. Whitlie said rather bluntly, "Oh by the way, Jane wishes you could have gone to Homecoming with her," or something like that. She then proceeded to explain that Jane knew I probably wouldn't, considering she had asked me to Spring Fling. Irony strikes again! I explained the sad reciprocation of my rationale to Whitlie. Jane was already going with one of my friends, Drew, so there would be no last-minute fix here.

If the mistake in not asking Jane to the dance wasn't big enough, I added to the problem soon after. I probably should have figured out some way to confront the situation, maybe asked her on a date since we already had different partners for the dance. Instead, I kind of just...ignored the situation. I think once before the dance I tried to bring it up, with something lame, and she kind of coolly rebuffed me, and dropped the matter. I ended up going to the dance with my friend's girlfriend - hoping that he would understand I just thought she was fun, and deserved to go to the dance. She was fun, and the night was fun, but I admit I spent a lot of the dance wishing I was with Jane. Oddly enough I got a bit of a chance at the actual dance. Amy - the girl I went with - had to go to the bathroom, and while I was waiting I bumped into Jane. Drew had similarly gone to answer nature's call, and I asked her if she wanted to dance, as long as we were both waiting. She kind of hesitantly agreed and we danced for half a song. Then Drew came back, and I don't think he was angry or anything, but he did seem a little confused. I awkwardly handed Jane over to him and said something stupid and left that situation as fast as I could.