How to Date Your Ex’s Best Friend

‘The ideal Evan Jacobs—the brash, confident stud I still want to be—existed for nine months of my sophomore year at the University of Chicago.’


It’s hard to go through life without regrets. Sometimes a decision that seemed perfectly appropriate at the time turns out to be a mistake. It’s happened many times in history: the Bush presidency, the XFL, Prohibition. For me, I realized that I should have been dating my girlfriend’s best friend a few weeks after I had become exclusive with my girlfriend.

Since college, my lack of confidence has betrayed me several times. I’ve acted too clingy with girls, I’ve tried too hard, and I’ve ruled out women just because they were attractive. The ideal Evan Jacobs—the brash, bold, confident stud I still want to be—existed for nine months of my sophomore year at the University of Chicago.

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. The lobby was large and inviting, and all the rooms had views of Lake Michigan, the Midway Plaisance, or the Chicago skyline.

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. They were a batch of children. One freshman in particular caught my eye. She was tiny, blonde, with a pointy nose and chin and large blue eyes. As soon as I saw her, I wrote her off as a girl that would scoff at any association with me. After all, she was hot—she wasn’t just cute or pretty. And damn, did she know it.


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? Should I only date within my own league? To be frank, the idea of “leagues” was frustrating beyond the fact that it was a sports analogy. I wanted to prove it wrong. I wanted to overthrow it. Just because a girl was more empirically attractive didn’t mean that she shouldn’t date me.

Convincing her I was a worthwhile pursuit—that was another matter. This blonde girl was decidedly out of my league. When I ran into her in the elevator one day early on in the year, I made a bunch of rapid-fire jokes. I spoke to her in the way I speak to many people, to enjoy the attention and not expect it to lead anywhere. She laughed at everything I said, but it meant nothing. Plenty of people who would never speak to me otherwise, let alone date me, have laughed at things I said.

In truth, I don’t really remember what I said to her, or how it happened, or what the details were, but I do know that I offered to help her with her chemistry homework a couple days after the elevator incident. The offer turned into our talking through the night and into next morning, neither of us sleeping. As a crazy coincidence, we discovered that we were neighbors. I lived in the last door of a hallway, she lived in the second to last. I’m not sure if we kissed that night or if it was the next night, but before I knew it, we were together, naked in my bed.


The world was inside out. Down was up. The sun revolved around the earth. She was mine. She liked me. A girl who was too attractive to be with a schlub like me had willingly joined me in a relationship that defied expectation and logic.

I soon learned that Christine was far from perfect. She was from a small town in Ohio and had grown up very poor in a family that didn’t place the highest value in education. She was the first member of her family to go to an institution with anything approaching the academic rigor of the University of Chicago. This made her insecure; she feared being stupid to the point of terror.

She was very kind, very nice, and although she was very intelligent, I found that there was something missing. She didn’t have the academic thirst that I had. She lacked the same cynicism, skepticism, and curiosity. Even a couple months into the relationship, though I was enjoying spending time with her, I had determined that I probably was not going to fall in love with her. The relationship was doomed to fail.


Christine had three very good friends in Broadview. One of them, Kathy, was a skinny Polish girl with squinty eyes and a long nose. She didn’t have Christine’s sex appeal, but she was undeniably cute—and she had one huge draw that I found myself not only admiring, but lusting after: Kathy was majoring in physics and math.

Science has always been my true mistress. It has an inherent beauty in its absolutism; it shirks sentimentality and pretension; it embraces the universe beyond the insignificant dramas of everyday life; it explains reality and existence more than religion or philosophy ever has. It should be no surprise, then, that I majored in mathematics myself. To find a girl who was fascinated with math and physics was a twofold boon: 1) a girl who pursued these areas of study had similar interests to mine, and thus would almost surely understand my worldview; and 2) science and math, as academic fields, are male-dominated—so the women in the field struck me as brave, exceedingly intelligent, ambitious, and far above shallow pursuits, like obsessing over makeup or dancing to bad music—i.e., things Christine loved.

While Kathy’s looks made her cute, her interest in science made her hot. And her own insecurities fueled my lust even more. She was the inverse of Christine: confident in her intelligence, but unsure of her looks and social skills. 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. Thus, even within a few weeks of dating Christine, I had fallen in love with Kathy.

I continued to date Christine. There was no obvious or overt reason to break up with her, so I decided to stay with it. 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. After the winter break, while Christine and I were in the middle of making out and reuniting, she began to cry. She had to tell me something, and I already had an idea what it was. Every time she went home, Christine would hang out with a group of local police officers. It was innocent, she said. They were her friends. They would get drunk with her and even smoke weed with her, but it was all in good fun.

I am far from stupid. They were men and she was an attractive female. There’s no such thing as innocence in those situations. 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.

I forgave her. Who was I to be angry? I didn’t love Christine. Sometimes I felt guilt for even continuing the relationship. Only now do I realize that this incident may have been her way of testing how I felt about her. If I truly loved her, I would have been much more upset. If I didn’t, I would have forgiven her. 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. I still don’t know how I managed to stammer through that one. I told her that I enjoyed that she loved me, and that one day I hoped to love her, but I just wasn’t sure, at that moment, if I was able to feel the same way about her, and I didn’t want to lie.

Though she said it was OK, two weeks later we broke up. I didn’t mind. All I could think about was Kathy.

To be sure, I felt somewhat guilty that I might hurt Christine’s feelings. But she had cheated on me; I’d done nothing wrong. I put Christine out of my mind. 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. I asked her to hang out, although she seldom did. I studied next to her. I told her about what was going on with Christine. This was my plan. First I would become friends with her. Then I would tell her how I felt. Then I would date her. Then we would get married. Then we would have children. Then we would both die and be buried next to each other. It seemed foolproof, and for the most part, it was.

The confidence I had gained from dating Christine had altered my personality. No longer was I a loser with low self-esteem. I had become suave, charming, and enticing. I felt no concern that Kathy would resist my advances.

It took no summoning of courage to ask Kathy out—the confidence was already there. 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. 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. 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 hugged her often. I took her out to dinner. I hung out with her in my room. Eventually, when I kissed her, I had no worries that she would give me her cheek or pull her head away.

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. I ran into her multiple times after the breakup while I was courting and later dating Kathy. I actually told her that I was dating Kathy, but she already knew—Kathy had told her much earlier on.

It wasn’t that awkward. Christine gave us her blessing, and started dating other men as well. She and Kathy remained friends. Maybe her guilt over cheating on me mollified any anger she might have (quite reasonably) felt toward us. Whatever it was, I had nimbly skipped my way through the minefield of dating two friends.

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. And for at least a month, dating Kathy was amazing. We would go to dinner, talk about physics, see movies at the campus theater, get coffee, meet each other on campus, etc. It was the ideal college romance. We even dabbled in marijuana. Of course, we also kissed each other and slept together—although therein lay some difficulty.

Whereas Christine had liked me too much, Kathy was more aloof. She never complimented me, never told me how cute I was, never told me how much she liked me. She didn’t try to hold my hand, she didn’t caress my back, she didn’t try to kiss me in public. When we did kiss, it was like I was introducing her to the concept of what kissing was.

She just wasn’t very affectionate. She wasn’t bursting to tell me that she loved me. She didn’t seem to understand how awesome I was, and in turn, I started feeling less awesome.

Kathy was shy. It wasn’t her fault. But I found my newfound confidence waning, and I flipped out.

If she didn’t think I was that great, shouldn’t she be with a guy who was? Someone she liked as much as I liked her? Someone she would want to be affectionate with?

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? So what if I thought she didn’t like me enough? She had agreed to be with me and that should have been good enough. If she had wanted to break up with me, she would have done so. But my newfound confidence had failed me. I was back to square one—I became the same neurotic, anxious, awkward, desperate jerk that I had ever been. And so she got away.

Like many mistakes in my life, I should’ve learned from it but didn’t. I second-guessed myself—and instead of vowing to trust my instincts in the future, I kept on doubting. I doubted my way through relationship after failed relationship. And it’s only now, 10 years later, reliving this disaster of a romance, that I’m figuring out where it all went wrong.

If I could time-travel and meet my 19-year-old post-Kathy self, I’d say this: You deserved her, dude. Fuck low self-esteem. The next time you meet a girl you really like—and trust me, there’ll be plenty—don’t give up on her. Because even if confidence can be a fickle mistress, regret will break your heart every time.

—Read Jacobs’s “Chronicles of a Phone Sex Addict” here.

—Photo quinn.anya/Flickr

 Reprinted from The Good Men Project

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