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.

Pool Party

Finally, I made it to my senior year. Setting girls aside, I couldn't ask for much more. I was excited to start school again (don't worry, that only lasts for the first week of school), and I had a variety of friends that were fun to hang out with. Lone Peak had great sports teams for me to watch. The first week back from school I decided to attend the annual back-to-school pool party. For various reasons, I hadn't attended the previous two pool parties, so I didn't know what to expect. I'm not much of a swimmer, and I didn't know who would show up. I wasn't disappointed.

The party started out as any good party should. I had a hot dog or two, and then played football - guys against girls. I saw Jane and said hello, but I didn't talk to her much because she was with fellow soccer player Nate, and I decided to stay low for some reason. I don't know what happened next, but after a little while, I was sitting cross legged on the cool grass, facing Jane. Nate had gone off somewhere, and it was my first time alone with Jane in a few months. We talked about all sorts of things, but we mainly focused on college. Jane tried to sell me on some small college in Massachusetts named Williams, and I tell you, she did a better job of it then their marketing department could have.

Other than dancing, I think Jane and I connect most when discussing intellectual things. She is brilliant, and there's no doubt in my mind that she'll change the world some day. She seems to think I'm brilliant as well, and there's nothing I can say to dissuade her. Even though she might overestimate my intelligence, I am smart enough to discuss philosophy, or politics, or literature. And unlike many other people she might try to converse with, I pay rapt attention whenever she speaks. In part because I like her so much, and also because I don't get the chance to talk about that sort of stuff with almost anyone else.

It honestly seemed like we talked for hours, but I assume it was actually a little over half an hour. I was already on cloud nine - that's such a weird phrase - after this talk, and I figured our time chillin' would be done. However, as I walked out of the grimy locker room and out into the pool area, I saw Jane walking out as well. We then waded out into the pool for a while, and then over to the hot tub - which was ridiculously crowded. After that I kind of backed off. It was probably cowardice, but I rationalized it back then by saying I didn't want her to think I was following her around. Thus, I spent the rest of the night getting schooled in water basketball (which was actually more akin to water football) and kind of walked off without any real closure on the night.

A Simple Summer

Three of my friends share a birthday at the end of May, so every year in high school we celebrated all their parties in one massive birthday bash. So during May of my junior year, it was party time again, and I was excited to talk to Jane again. I got my chance in the middle of the party, when everyone was starting a movie. The conversation bolstered my hopes even more. I don't remember what we talked about, but the feel of the exchange was similar to when we talked during the assembly a few days earlier. I was starting to get a little more confident. She had asked me to a dance, and then we had two good conversations. Looking back, I know it sounds ridiculous to become confident because of a couple "good conversations," but I was just silly back then I guess. As good as the conversation was, however, another major roadblock presented itself. Jane's dad lives in Boston, and she was going to spend a large chunk of her summer there. Just when things were looking promising, I wouldn't be able to see her until July.

While she was gone, I got on with my life. Two of my friends had budding romances over the summer, and I was kind of forced to play third wheel (or maybe fifth wheel?) over the summer. It was a fun group to hang out with, but I was a little jealous - I wanted to know what it was like to have a girlfriend. At some point during the summer I emailed Jane and she responded with a long, funny email of her own, that made me like her all the more.

Things get interesting

I have mentioned my intuition a couple times previous, and in both those cases I was right. This is how I began to rely on my intuition to much, one of my several tragic flaws (assuming I'm a tragic hero). The following story is iconic of this flaw, and you will easily see why. It was near the end of school. We were having an assembly of some sort, I think it was to celebrate the boy's soccer team winning state (We won five state titles that year). I found a seat to myself, and was soon joined by Jane. Now this should have been viewed as nothing. After all, we were pretty good friends at that point, and I was sitting all alone. However, at that time I felt like there was something more to that encounter, and actually I stubbornly hold onto that thought to this day.

Don't worry these revelations didn't occur simply just because she sat by me. She just had a different . . . attitude I guess. She seemed really giddy. She asked me if I liked Cyndi Lauper. She shared her iPod with me. All in all, it seemed a little flirtatious, and very different then any other time we had talked. She wanted to take a picture with me, and sadly I ruined that moment by deleting the picture because I looked stupid in it. That is about it, and though the event was undeniably small, its affect on me was huge.

If by that point I hadn't already had a complete crush on her, I certainly did now. And for once in my life, I sensed that there was a chance it would be reciprocated. I honestly didn't know what to think. All my life I had liked girls and expected nothing back. Now I was faced with actually trying to find out her feelings, and I had no idea how. So with my typical brave behavior, I decided to wait it out for a while, and see what the summer would bring.

The Fling

My junior year continued to cruise on by, and my chances of finding a woman were about the same as my chances of getting a 4.0 that year - nil. I did finally go on my first date with everyone's darling, Samantha. Seemingly the only guy I knew that didn't have a crush on her at some point, it seemed at least somewhat ironic that she was my first date. That was during the winter, and I hadn't been on another date heading into spring.

Here, the order of things gets lost on me, but I'll start with my 17th birthday, and what a crazy day that was. I had been planning an ambitious party, (ambitious because I intended to invite all my various groups of friends) but my high school's basketball team threw a wrench in my plans. In glorious fashion we won the state championship, and one of my friends started for the team. While I had spread the word earlier that I would have a party at my house, many of my friends were swept up in the euphoria of the moment and started wild calls of "party at Matt's house!" (Matt being my friend on the team, of course). Ever the willing martyr, I shrugged it off and decided that only my closest group of friends - those who didn't know Matt - would show up. While a horde of my friends did go to Matt's house to celebrate, surprisingly they soon came over to my party and I didn't know if my house would hold everyone.

"Where is Jane in this story?" you might be asking. Well, as I understand it the reason everyone eventually showed up at my house was in large part due to the efforts of Jane. Using her influence, Jane reminded the mob of my party, and convinced them to attend. In retrospect, I almost wish she hadn't convinced them, because the disparity between my different groups of friends made the whole thing awkward. However, it truly is the thought that counts, and I was happily surprised that Jane did that for me.

Perhaps it was due to the aforementioned anecdote, or it was just my generally spot-on intuition, but I began to think (hope?) that Jane would ask me to Spring Fling. As far as I knew, Clint was no longer in the picture, and I thought there was enough between us for her to ask me to a dance. Time passed, and I began to lose faith in my intuition, but right before the dance I received a mysterious brownie on my doorstep. After eating my way through the good-sized dessert, I found out that Jane had indeed asked me to Spring Fling. We went as part of a larger group that consisted mostly of seniors that I hardly knew. For dinner, we had KFC. This truly terrified me, because I am a messy enough eater without greasy finger food thrown in the mix. I found myself being terribly self-conscious about everything I did. Luckily, the KFC dinner went without too much incident. We also played a small game in the living room of whoever's house we were in, in which you tried to pass secret signs behind a person's back. Sorry, I just can't really describe the game very well, suffice it to say I don't like it very much. The room was small, and the group of people large, so Jane invited me to share a chair with her. Now those of my friends who have actually kissed a girl or held a girls hand would think nothing of this, but to me and my inexperience, I was wowed to sit that close to a girl. Sad, I know.

While the date had gone well up to that point, when we finally hit the dance floor, it really shined. I guess Jane had never really seen me dance before, because she was obviously impressed. Well maybe impressed isn't the right word . . . let's try entertained. While every other time I'm around girls I'm stiff and uncomfortable, something about dancing lets me lose my inhibitions. I know that sounds like the plot of at least a dozen movies, so I pardon my lack of originality, but its true. I had a blast dancing, and I was fairly sure she did as well. This is also - I believe - where we first danced to the Spice Girls, a song that we have danced together countless times. All in all, it was a nice little fling.