Top Five Most Memorable Break-Ups

My desert-island, all-time, top five most memorable break-ups, in chronological order:

1. Amy
2. Kirsten
3. Erin
4. Polly
5. Jennifer

Those were the ones that really hurt. Can you see your name on the list?

1. Amy (1987): Ok, so I was sixteen, so it’s scarcely admissible. But remember how things felt when you were sixteen? Major drama. On-again, off-again, on-again, knockdown, drag-out arguments at our locker in plain view of the entire school, ending one sunny fall afternoon in Valley Forge Park. “You’re breaking up with me over a Wawa hot dog?” Yeah, I was. Remember these? Well, this was one of those.

2. Kirsten (1990): I spent the better part of my freshman year at Syracuse University writing letters (this is pre-email, for God’s sake), making late-night phone calls, and generally missing my senior year crush. But then, I cheated on her the first night at school with some raven-haired, red-lipsticked girl from Long island thus commencing my still-standing attraction to New York City Girls. It was an ugly and immediate ending when she found photos of another woman in my wallet. Note to future generations: don’t even try to date someone through the high school/college transition. Guaranteed failure.

3. Erin (1994): This one really, really hurt. She was The Artist. I met her at my first performance with my college alt.rock band, Smokey Junglefrog. She had sparkles on her face, wild blonde hair, and was wearing a thrift store leather jacket with tassels. We had ten romantic days in Tuscany, weekends on the Cape, a week in the mountains above Telluride, and three years of memories in-between. I graduated before her and moved to nearby Saratoga Springs. She worried that she hadn’t dated anyone else in college, so broke up with me one hot August afternoon. She drove off, leaving me on the front stoop in tears. When I went inside, my brother handed me the bong. I didn’t put it down for five years.

4. Polly (1999): At college, she was the devastatingly beautiful and pathologically outgoing sorority girl down the hall. I didn’t stand a chance. But somehow, for some reason, she liked me too. But I was dating Erin. So when I moved to New York, and had a proper job, I looked her up. We dated for three years. The ending was a long, dragged out affair. She wanted to get married. I wanted to get stoned. Finally, enough was enough, and we called it a draw. But not before months and months of painful goodbyes.

5. Jennifer (2002): When she walked into my office, I said to myself, ‘Now there’s a reason to love again.’ And she was. Long story short, I (still) wasn’t ready to get married. And yet I endeavored to be: committing, uncommitting, committing, and uncommitting over and over and over. God bless Jen her patience. Fortunately for both of us, it ran out.

Despite all the gloom and self-doubt that bubbles up from deep when you get dumped, none of the above represent my last or best chance of a relationship. Just so you know.