Grading My Ex-Girlfriends

Keeping track of stuff is important. Or maybe keeping track of stuff isn’t that important. Who can say, really, in this crazy “jamboree” that we call “life”? ANY-way, I like to keep track of stuff, and I like to give stuff grades. For example, I have all the coffee mugs in my kitchen rated by order of preference, going from coffee mug Number 1 (which gets an A+), down to coffee mug Number Last (which is really so, so ugly, but which I still use sometimes because I feel guilty for ignoring it).

But why stop with coffee mugs and other household objects? Why not grade and rate everything, even when it’s inappropriate to do so? It’s a rhetorical question; really, I have no choice in the matter – I am obsessive, and I grade everything in my head. So here, as part of a potentially endless series of these articles, is a column where I give grades to my ex-girlfriends.

Yes, we were in relationships, and now they’re being summed up in a way that allows very little room for nuance. That might be annoying, but hey, I would think it was funny if someone did it to me. Here are my exes, graded on a curve; from Kailey, who gets the top grade, to Sarah, who doesn’t get such a great score. Enjoy. And obviously, all the names have been changed, and some identifying details have been changed as well in order to protect the guilty/innocent.

GRADING MY EX-GIRLFRIENDS

Jessica: She had reddish-brown hair, and blue eyes (I think). We didn’t go out for very long. She broke up with me.

There was nothing super memorable about this relationship, except that Jessica was a fashion model¹. This was an important step for me as part of my never-ending attempts to convince myself that I’m not a nerd, and that I’m a stud who can attract hot chicks. I will never be convinced about this, probably because I’m not a stud who attracts hot girls. I dated Jessica, and I’ve dated two strippers, and the whole time I was like, “Am I still a nerd? How can I be, if I’m dating a stripper? Etc…” But really, if you have to ask yourself stuff like this, then you still are a nerd, so the question contains its own answer, which is nice.

Anyway, Jessica was indeed a model, which meant that for the brief time that we dated, I got to practice saying things like: “Yah… so she’s a model… pretty boring really… that whole scene is getting pretty played out… Oh, is that my beeper? Well, gotta jet… late to meet J at Skybar… Ciao…” Meanwhile, my friends would shake their heads sadly, staring blankly at me with a mixture of bemusement and despair. Grade: B

Alexandra: She had dark hair, and I have no idea what color her eyes were – why can I never remember what color people’s eyes are? I’m red-green colorblind, which probably doesn’t help. But I’m looking at Alex’s non-blurred-out photo right now², and I still can’t tell what freaking color her eyes are. Brown? Green? I guess it’s one of the two.

I met Alexandra on an online dating site; lame, I know. And though I generally find cheating on girls to be so exhausting as to cancel out the minor excitement of getting to have sex with someone else for two weeks, Alexandra didn’t trust me, so she posted a second (fake) ad online with the picture of some actress. She wrote to me and I wrote back. As a result, for several weeks Alex enjoyed the fun experience of reading my attempts to seduce another girl, who was of course her. Not surprisingly, she broke up with me. What is surprising is that I drove straight to her apartment and convinced her to mess around/get back together with me. How I did this, I’ll never know, but I had had a lot of coffee to drink that day.

Even more intriguingly, as soon as I convinced her to get back together with me, I felt this crushing sense of boredom and being-trapped-ness, and though I promised that I would call her the next day, I didn’t. The rationale behind my behavior is:

1) I am a jerk.

and

2) And that’s it.

Also, one time when Alex and I were having sex on New Year’s Eve, we broke my futon, sending it crashing to the ground beneath us in five different pieces. You might be imagining this as a scene of high passion, full of the sort of violent sexy hot thrusting action that would cause a piece of furniture to break. But then, you’d also probably be imagining a more high-quality, sturdier, and better-constructed futon. Grade: C

[No photo here, for obvious reasons] Carrie: Black hair, black eyes. Carrie was the only girl that I ever had to check into a mental institution (and the police had to break down her door). On the other hand, she also looked like the cute-yet-mean Chinese girl from “Crouching Tiger, Hidden Dragon,” who is kind of my dream girl. You know the girl that I mean — whatshername – the younger one from the movie; the one who hits that guy on the head with a rock.

…And hey, does anyone else find that scene to be oddly erotic? When the girl hits that dude with the rock? Or does liking that mean that I’m a weirdo, or a… masochist? I hope I’m not a masochist; that would suck. Also, apparently I don’t even know how to spell “masochist,” because it took me three tries to type something that spell-check could even recognize.

Yes, so Carrie looked just like that girl from “Crouching Tiger.” Or maybe she didn’t look like that girl. Maybe it’s just that Chinese people look similar to me. I don’t mean that in a racist way, but the whole time that I was dating Carrie, I was worried. You know when you break up with someone, and then everything reminds you of that person, and you see them everywhere? But 40% of Asian girls already looked like Carrie to me. And then, sure enough, I did finally break up with Carrie, and then I was walking through Chinatown, and I was like: “Everything I see makes me think of her!” Which wasn’t fun.

To sum up, the whole relationship thing was a draw – Carrie’s physical resemblance to my dream girl essentially canceling out the fact that I had to check her into a mental hospital, which really sucked. The two things negated each other, which leads to a wishy-washy grade. Grade: B

Megan: Megan had red hair and green eyes. There wasn’t too much going on here, except that she had the words S-I-N-N F-E-I-N tattooed across her toes. That’s cool, I guess. So, she was an extremist Irish Republican – big whoop; I can handle that. See? I don’t feel the need to over-analyze every relationship. Grade: B-minus

Sarah: Blond hair, blue eyes, Nordic-ish, etc…

Usually, I try to have a reason when I break up with someone; just helps me sleep better at night. But in Sarah’s case, she was pretty, smart, funny, had a beautiful apartment in Park Slope, a sexy, gravelly voice, and had recently sold the screenplay for “Starsky and Hutch” to Warner Brothers for fifty thousand dollars. Nevertheless, I broke up with her, because… what was my reasoning again? According to my friend Dan, it was because, quote, “Dude, you complained that her breasts were too big and she could have an orgasm way too easily.” Good one! Way to think things through, self!

In my defense, there are breasts that are so large that they flop disturbingly to the side, and Sarah could have an orgasm much much too easily; just a thirty-second strumming of the fingers and she was done. For her, having an orgasm had all the sexual difficulty level of playing with one of those cup-with-a-ball-on-a-string toys that you used to have as a kid. Oh, whoops, I got the ball in the cup! Oh, look, I did it again! In fact, this one time we were having sex, and I got caught in one of those awkward sexual positions where your legs fall numb, and you can barely move, and every muscle in your body is straining to collapse, but Sarah was already doing the strumming thing with her fingers and was all like, “Do it! Do it harder!” and I started laughing, saying, “Do what? Stay motionless and try not to collapse on top of you?” and she was really mad at me.

So no, definitely a great decision to break up with her. And I’m sure all my rationales were of great consolation to me as I wandered the streets of New York in mid-winter, lonely and bereft, watching gigantic city buses cruise past with full-length “Starsky and Hutch” posters on their sides, with Ben Stiller and Owen Wilson staring down at me with their dead, vacant eyes. …Wasn’t it Dostoevsky who said that if people lived in a beautiful crystal palace, they would have to smash it just for kicks? Whatever. I’m sure he’d be with me on this one and give me a grade of: D-minus

[No photo, once again; duh] Kailey: Blond hair, no idea about the eyes. Kailey wasn’t technically my girlfriend, since she already had a boyfriend and I already had a girlfriend, but we did have sex while we were [deleted], while I was driving a minivan, on the freeway, which was one of the most dangerous things I’ve ever done and I still feel really, really bad about it.

And as we were doing it — having sex while driving, I mean — I had plenty of time to look out the windows at the other people on the highway that night, and I saw lots of happy families in station wagons and lovers in convertibles going on moonlit drives to upstate New York, and I thought of what we were doing, and I thought of our significant others, and then I sort of suffered through this Bret Easton Ellis kind of moment where I felt like I would never feel good or pure or innocent ever again, and I was sure that I was going to crash the minivan into a concrete divider and be played in the movie version by Robert Downey Jr.

But I didn’t crash and Kailey eventually married her boyfriend and had a baby; plus, her first novel is being made into a movie starring [name of person deleted] — so everything kind of worked out in the end. Therefore, I’m going to cautiously give myself a grade of: A-minus

I might also mention here that Kailey was born in [name of tropical place deleted] and her family was ridiculously wealthy, and she grew up in a mansion and had small [deleted] monkeys that would perch on her shoulders as pets. As a kid, I wanted all of that: the mansion, the monkeys, and the money. I would have fed pieces of fruit to the monkeys.

Ileana: Brown hair, blue eyes? Maybe? Probably? Who knows? Anyway, as it turned out, Ileana was a famous international photographer who was shot by an Israeli paratrooper while on assignment in [deleted], thereby causing a major international incident in which both the U.S. and Israeli governments became involved. And I wouldn’t have known any of this, if it weren’t for the fact that I do obsessive-compulsive Google searches on everyone I meet.

As a result, when Ileana told me about it, three weeks into the relationship, I had to act real surprised and shocked-ish, which was tough. “Really, you were shot while you were on assignment? …Um, get out. You don’t say. Um, huh. Where was it? Like, were you shot in the butt or something? It was in the butt? Weird. …Say, this isn’t the kind of situation where like the U.S. government becomes involved or anything like that, is it?” The moral of this story being that Google searches can backfire like that; sad. Grade: C-minus

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