The lobby was large and inviting, and all the rooms had views of Lake Michigan, the Midway Plaisance, or the Chicago skyline. She was tiny, blonde, with a pointy nose and chin and large blue eyes.Because I already had a year of college under my belt, I felt confident among the wide-eyed freshman who populated the majority of the dorms in broadview. As soon as I saw her, I wrote her off as a girl that would scoff at any association with me. Just because a girl was more empirically attractive didn’t mean that she shouldn’t date me.She laughed at everything I said, but it meant nothing.

She never complimented me, never told me how cute I was, never told me how much she liked me. But I found my newfound confidence waning, and I flipped out. So I did one of the toughest, stupidest things I’ve ever done: I broke up with her.♦◊♦So what if I thought I wasn’t good enough for her? She had agreed to be with me and that should have been good enough.

She didn’t try to hold my hand, she didn’t caress my back, she didn’t try to kiss me in public. She didn’t seem to understand how awesome I was, and in turn, I started feeling less awesome. If she didn’t think I was that great, shouldn’t she be with a guy who was? If she had wanted to break up with me, she would have done so. I was back to square one—I became the same neurotic, anxious, awkward, desperate jerk that I had ever been. Like many mistakes in my life, I should’ve learned from it but didn’t.

She had to tell me something, and I already had an idea what it was. They would get drunk with her and even smoke weed with her, but it was all in good fun. Over the break, Christine had cheated on me with one of the police officers, and to make it worse, they had had sex in the back seat of his police cruiser. If I truly loved her, I would have been much more upset. She had gotten her answer.♦◊♦It was only about a month later when Christine told me that she loved me, and I was put in the awkward position of not being able to reciprocate. Whatever it was, I had nimbly skipped my way through the minefield of dating two friends.

Every time she went home, Christine would hang out with a group of local police officers. I still don’t know how I managed to stammer through that one. Nothing was going to stop me from advancing on the girl I knew I wanted.♦◊♦Over the next few weeks, I thrust myself into Kathy’s life. The thrilling thing wasn’t that I ransacked a clique one by one—it was the fact that yet again, the girl I wanted became my girlfriend.

At the same time, I would talk with Kathy every time I saw her, and even started visiting her in the lounge when I knew she was there studying.♦◊♦At some point, Christine screwed up. Sometimes I felt guilt for even continuing the relationship. You should let me take you out on a date.”Sure enough, she agreed.♦◊♦I began holding her hand when we were alone, getting her used to touching me. I ran into her multiple times after the breakup while I was courting and later dating Kathy.

After the winter break, while Christine and I were in the middle of making out and reuniting, she began to cry. There’s no such thing as innocence in those situations. Only now do I realize that this incident may have been her way of testing how I felt about her. I actually told her that I was dating Kathy, but she already knew—Kathy had told her much earlier on. Christine gave us her blessing, and started dating other men as well. Maybe her guilt over cheating on me mollified any anger she might have (quite reasonably) felt toward us.

In September 2000 I lived in a dorm called Broadview, an architecturally beautiful building that had previously been a high-class hotel in the ’20s.

All the rooms had their own bathrooms, and most were singles, though there were a few rooms with roommates.

And, as every socially awkward male knows, the only thing more attractive than a hot girl is a hot girl who has no idea she’s hot. About a month after I had broken up with Christine, I was in the study lounge with Kathy, and I told her that there was something I wanted to talk to her about. Eventually, when I kissed her, I had no worries that she would give me her cheek or pull her head away.

Thus, even within a few weeks of dating Christine, I had fallen in love with Kathy. There was no obvious or overt reason to break up with her, so I decided to stay with it. I apologized for what I was about to say, and then I told her I wanted her—I had wanted her ever since the moment I met her.“I don’t care about Christine and you shouldn’t either. Christine actually happened to live in the next dorm room over from mine, and I had to pass her room every time I went anywhere.

After all, she was hot—she wasn’t just cute or pretty. Perhaps it came from years of rejection and snubbing from the most attractive girls, but at the time, I had taken to heart this idea of “leagues.” Is she out of my league? To be frank, the idea of “leagues” was frustrating beyond the fact that it was a sports analogy. Convincing her I was a worthwhile pursuit—that was another matter. When I ran into her in the elevator one day early on in the year, I made a bunch of rapid-fire jokes.