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Things I've Learned From Women Who've Dumped Me - Ben Karlin [55]

By Root 281 0
sitting at a restaurant while the waiter describes the mouthwatering specials—then returns to say they’re all no longer available. (Oh, and by the way, the restaurant is out of food altogether. And you have to go in the back and help with dishes. And you won’t get paid.) Or maybe it’s like the dot-com boom. This was the midnineties, after all. Every day I’d read about another twenty-two-year-old who sold his online turtle aquarium company for a quarter billion, while I scraped by on a journalist’s salary, sucking down the bitter cocktail of jealousy, longing, and regret.

I can’t say for sure why I kept coming back to the dirty gals. Partly, I think, bad luck. But partly, the maddening fact that these women all tended to be interesting and funny.

With Chloe, I tried this tactic: Whenever she’d talk about her boyfriend du jour, I’d try to come up with all the reasons she and I would make a terrible couple. She was a commitmentphobe. I could have been happily married at twenty-two. She’d stay out till four every night. I don’t like going outside, unless it is to evacuate a burning building. She loved going to earsplitting concerts. I got cranky when NPR was on too loud. A valiant attempt, but it didn’t work.

What made it worse was that everyone assumed we were a couple. Even my family. When I wasn’t dating anyone—which was not uncommon—I would take Chloe to family functions, which always resulted in a similar scene. We’d walk in—Chloe would be wearing, say, a cleavage-bearing baby T, a micro-miniskirt, and knee-high black leather boots—and she’d whisper to me, “Everyone’s staring at me.”

“Naaah,” I’d say.

Then I’d look around and, well, yes they were. In fact, they all would have their eyebrows raised like Spencer Tracy when Sidney Poitier entered the dining room. One time, my aunt gathered up enough courage to ask Chloe about her wardrobe. Chloe explained that she sees getting dressed every morning as a chance to put on a costume.

“Ohhhh, I understand,” said my aunt. It finally made sense to her: She is not an actual prostitute. She just puts on a costume that makes her look like one.

Chloe encouraged me to date other women, which was hard when she was around, since Chloe could be an intimidating, cleavage-bearing presence. One time, she prodded me into my first pickup attempt at a bar. Here’s the quick version: We spotted an attractive brunette drinking Dos Equis with a couple of friends. “Come on,” said Chloe. “Let’s go.” She would be my wingwoman.

We approached, and Chloe engaged the woman in a conversation. After a minute—and I can’t remember how it came up—we learned that both the brunette and I were born in 1968. Now, 1968 happens to be pretty much the worst year in American history: the assassinations of Robert Kennedy and Martin Luther King, the Tet Offensive, and on and on. So whenever my birth year came up in conversation, I would comment, “Such a wonderful year, 1968. So proud I was born then.” At which point I’d list all the horrible things that happened. It’s not Noël Coward, but I’d usually get a mild chuckle. So I tried it out.

“Such a wonderful year, 1968. The assassination of Martin Luther King . . . ”

And then I stopped. I lost steam. I’m not 100 percent sure why. I think I realized the joke was iffy, so I bailed. It didn’t seem appropriate for the first couple of minutes of conversation. Unfortunately, it was much less appropriate to stop where I stopped. The brunette recoiled, repulsed and frightened. She shot me a look, “Please don’t kill me. Just go back to your Aryan Nation meeting.” She walked away without another word. (I think it goes without saying, I have since retired that joke . . . and have never again spoken to strange women in bars.)

Maybe I unconsciously torpedoed the pickup attempt because I was so infatuated with Chloe. Something had to give. So one summer night, I finally made a pass at Chloe. It was the worst-planned, poorest-executed pass of my life. She was sleeping over at my apartment, as she did whenever she didn’t want to schlep home. That very night I had been dumped

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