Love & Sex

Five Relationships Distilled Into Their Best And Worst Moments

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"The effect is akin to watching Casablanca with little bits of Plan 9 From Outer Space spliced in."

As I get older, my memories of old relationships are slowly decaying into a series of cinematic montages, losing all their connective exposition and falling into piles of striking images. The two things that are most likely to survive are the moment I knew I was in love, and the moment I knew I things were crashing and burning. The effect is akin to watching Casablanca with little bits of Plan 9 From Outer Space spliced in. Observe:

1. Marcy

Background: Marcy was a rebound from a rebound, the product of being in an unhappy relationship which was itself the product of another unhappy relationship. Vulnerable, I was drawn in by her downright nasty attitude and black humor. Marcy was all about vice: we'd spend our days smoking cigarettes in her bed, watching trashy TV, having sex, eating McDonald's, and drinking vodka. I'd say she was as close to insanity as anyone I had ever dated, and it intrigued me to no end.

That moment: Before Marcy, I had dated a girl who praised my every move. It sounds pleasant, but it felt like an act. So Marcy's frankness, while mean, was a welcome change. I realized I liked her when she said something I hadn't heard in years. One day, I said, "You know, I think you're perfect." To which she replied, "Why would you do that? Take this stupid little thing we're doing and ruin it with 'I think you're perfect.'" I was instantly smitten. She was mean in the most romantic way.

That other moment: Marcy and I were blessed with the same type of overwhelming anxiety and, after a while, it all became too much. She just hated… everything. Eventually I biked to her house in the rain to see her. I was drenched, tired, and down; she was drunk and started making out with another guy right in front of me. Suddenly "frank but mean" didn't sound so good.

2. Robin

Background: I'll always consider Robin my first love. We were fifteen and incredibly stupid. I thought she was the last person I'd ever love, and I dragged myself through the mud at her every command. I was so dumbly in love that I overlooked every flaw in her personality.

That moment: She was my first kiss, my first hand-holder, my first hug, my first everything. And this was after fourteen years of being invisible to the opposite sex. This itty-bitty amount of attention was mind-blowing to me. So one day, when she looked me in the eyes and said, "I think I'm falling in love with you," I melted from top to bottom and fell deeply in love with her back.

That other moment: A few days later, I was talking to my best friend after school, and he said, "Robin was over at my house today. You should stop seeing her."

I said, "She actually told me she loved me."

He said, "She said the exact same thing to me today."

Nothing ever happened between them, because he was my best friend, but I knew things would never be the same. We continued our on-and-off romance for years, but I would always end it. She would tearfully ask why and I'd give a stock answer like "I'm not at a point where I want a girlfriend." But in my mind it was always because I was cruelly double-crossed.

3. Olive

Background: We dated for six months, but I just wasn't into her. So, in the traditional manner of ones who are not into others, I was a bad boyfriend. I never paid attention to her, compared her to other girls I had dated, and eventually ended the relationship via text message. But I always made everything out to be way more wonderful than it was.

That moment: It was right out of a bad movie. We were huddled up together on a bench outside the mall, and it was snowing. (It was probably the third snowfall of the year, but my inner script doctor tells me I watched the first snow with her, so let's go with it.) Right then I decided, hey, I could be in love with this girl. So, again, right out of a bad movie, I wrote "I <3 you" in the snow. It was awkward, but she laughed and replied, "Aw, I heart you too," and we probably kissed. God, I wanted to be in love so badly. I wanted to sweep a woman off her feet, but I was just so impatient.

That other moment: We grew apart, but wouldn't break up. We were the still-mostly-intact roadkilled squirrel that you swerve to avoid running over. At lunch one day, I found her eating outside with her friends and sat next to her, mostly out of a feeling of obligation. She awkwardly tried to accomodate me and them, knowing I didn't integrate into her friend group very well. Finally, she turned to me and said, "You don't have to sit here if you don't want." Exit squirrel.

4. Lindsay

Lindsay and I met on a dating site and were pretty gross with each other from the beginning. Before we even met, she sent me naked pictures, wrote the dirtiest texts, and threatened me with total sexual domination. After texting back and forth for a week or two, we decided to meet at my favorite bar in Brooklyn. I was a tad nervous about living up to her expectations, so I drank a lot before I got there. Lindsay texted me saying she was running late, so I drank some more while waiting. By the time she showed up, I was drunk out of my mind. 

That moment: Alcohol makes people pretty damn enthusiastic about each other. So, as we were holding hands, I thought I could feel a connection forming. We didn't have a ton in common, but there was chemistry. We went home that night and did various profane things to each other.

That other moment: It didn't take long to realize that we, in fact, had absolutely nothing in common. On our third and most sober date, I found each bit of conversation was more vague and vapid than the last. Every moment became a struggle, and we both knew it. The clincher came when we took a thirty-minute train ride to buy pot from her ex-boyfriend. I watched her smoke and flirt as I sat there petting the guy's dog.

5. Sasha

Sasha started off as the most romantic fling I had ever experienced. We were acquaintances in high school, but lost touch after we went to college. It wasn't until we randomly ran into each other at a dingy doughnut shop in Connecticut that I started to fall for her.

That moment: We started talking and couldn't stop. I was dumbfounded. We were the victims of accidental romance, being hurled through the majesty of the universe by complete chance. We walked across a bridge at two in the morning and held each other as a meteor shower happened above us. (Seriously.) I thought I'd found the one when we were in each other's arms. But…

That other moment: She was racist. Not in a "joking" way. In a serious, I-hate-people-who-aren't-white way. There were absolutely zero indications until one night when we were watching President Obama on TV, and she described him as "absolutely vile" and "a fucking [n-word]." Needless to say, that was the end of that montage.