Alyson
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So it starts. We're dating. We go out on weekends. We talk on the phone. Life is good. But there's a strain, somewhere. It's in the form of a guy named John Shuit. The guy who'd set us up.
For some background on Shuit and I, read the Gwyneth story. Same guy. Anyway, unbeknownst to me, John and Alyson had actually dated the year before. This came out in little hints over time. It also seemed that John didn't like our budding relationship after he'd helped it bud and so from time to time would sow seeds of mistrust.
Meanwhile, Kip was learning many new things about Señor Shuit from other friends and getting really scared by what he heard. I won't publish them here (libel suits being really easy to file in America) but suffice it to say that I was a little dismayed that Alyson still held John's opinion so highly.
I remember one day during play practice, she came up to me and said, "Hey, guess what I heard today? You and I broke up!" Earlier that day, John had asked me if we had and I said no. It seems really juvenile right now but it was a shock. At the time, we'd been going through a tough time. Triggered by John's innocent suggestion to Alyson that I just saw her as a trophy.

I should've tried communicating before.
The first one of these really uncomfortable times came around the time of two months. Valentine's Day. The first Valentine's Day I'd had with an actual Valentine. But things weren't going so well. It was due to the fact that we weren't going to Snow Ball, but instead to this Viennese Ball that I had committed to playing.
See, Snow Ball was this school dance (I was pretty sick of school dances, especially after Homecoming) and Viennese Ball was this expensive fund raiser down town for the upper crust. I was playing in the orchestra and so got to go to the beginning for free. Alyson felt really uncomfortable going but I dragged her to it, really.
Was I wrong? Probably. But we had a good time. In fact, she knew almost as many people there as I did. So things turned out well in the end. But at that time, Valentine's Day, Alyson was not happy about the situation.
I was even expecting a breakup, just from an extrapolation of past events. It'd be only fitting, right? But wonder of wonders, Alyson and I actually talked things through and kept going. And had another month that was almost as good as the first one. I should've tried this before. Well, actually, I never had the chance before since the past girls had just sort of made up their minds about things and then informed me of their decision. But perhaps if there'd been more communication in general, things would have been better.