There are so many ways an ex can make you miserable. Jealousy, which you have no excuse for expressing. Four a.m. phone calls begging for just one more chance. Four a.m. phone calls "just to remind you what a cunt you are." Painstaking negotiations of how the relationship will progress: "So, now that we're broken up, does that really mean we can't sleep next to each other?" Well, yes, that's actually exactly what it means.

    It makes perfect sense to exorcise the ex from your life entirely. But that's a problem in a world where the paradigm is the Cool Ex — a drinking partner, someone with whom you exchange barbed opinions on your new loves. You're friends, but even better, you get to release any lingering resentment by teasing each other about sex. You force yourself to be casual, to listen to the details of your ex's new sex life, so you don't seem overly emotional, crazy, attached. Ultimately, if you do stay close with an ex, you must have a good reason, because you're risking a lot of pain. They'd better be a fucking amazing person — or someone who can get you into fucking amazing parties.
    Rusty Schwartz is my Cool Ex. We went to college together and made out a few times our senior year. There are a lot of reasons we should have been attracted to each other — we both loved Gram Parsons and whiskey, we both went to the same bars, we were both total insomniacs and spent dawnish hours IMing each other. However, it basically came down to this: he was Boyslut, I was Girlslut, and a hookup was mathematically inevitable. After a few nights spent in each others' rooms and a few socks lost, I drunkenly propositioned him, he soberly refused, and that was that. We started building a makeshift friendship out of shared stories of romantic mishaps, which we talked about openly, maybe cockily, lest one of us think the other had placed any real stake in our brief . . . whatever:

    "So, Laura was over last night. Did you know she has a tattoo of a fucking butterfly on her pubic bone?

    "Hey, Rust, can I borrow five? I left my wallet at this guy's house. Guess that's what I deserve for fucking a grad student, huh?"

    "You know what you shouldn't do? Look up when you're going down on a guy and say 'You know, the semiotics of this position are very degrading.'"

    "You know what you shouldn't do? Get blown by women's studies majors. Anyway, you know who gives good head? Steve Luca. Blue ribbon, that kid."


    Two things were happening via these crude, brief conversations. First, I was becoming actually, genuinely fond of Rusty. At the same time, I was becoming totally obsessed with his sex life.
    Wonder why. Guess Cool Ex isn't that cool. Guess once I've woken up next to someone, no matter how much all I want from them is friendship, I feel a certain investment in their future hookups. It's narcissistic, but not exactly jealous. More like a deductive: "He hooked up with me and her, what does that say about me?"
    The fact that Rusty could smile and pat me on the back while practically killing himself over skinny girls who cruelly ignored him and called their purses "baguettes" said things about me that I did not want to hear. Specifically that maybe I was a little too coarse, aggressive.
    Before long, Rusty and I graduated. He moved back to Chicago, I stayed in the city. We kept in touch, gave each other dating tips, just like we had in college. So it didn't feel strange that he asked to stay at my place for a week last fall.
    I knew that when he visited, there would be girls involved. There were never not girls involved. How could there not be? He had this tousled hotness: smiling brown eyes and a spine-melting smile. The way he wore a plaid shirt — untucked, the slightest bit fitted, two buttons unbuttoned, sleeves rolled up above the elbows! "He's Chicago cute," I explained to my roomate, Lili. "Like a folk hero. Mixed with a baby panda." She nodded and went back to reading her book, then looked up:
     "One of the hot baby pandas?"
    Enter my plan to set Rusty up with Lili.
    But why would anyone fixate on anything quite this twisted? That is, the union of a much beloved, well-worn ex and a much-beloved, virginal roommate?

    1) I love Lili and Rusty and want them to be happy.
    2) Lili, green but unwilling to deal with inept fumblings, would fare well under Rusty's sensitivity and, um, experienced affection.
    3) Rusty would be distracted from the Baguette Girls by Lili's candor.
    4) They weren't going to have sex (Lili, I think, is holding out for someone who lives in the same city as her), fall in love, make each other elated or miserable.
    5) So I'm not going to be jealous or regretful.
    6) In fact, I'm going to be totally in control of this situation the entire time.
    Perfect. If Rusty and I bonded by talking about hookups, image how much we'd bond if he hooked up with one of my best friends?


One night, as I share a cab home with Lili, it comes to light that she, at age twenty-one, has never really seen a penis. Lili is beautiful; anyone will tell you that. But she's seen her mom unhappy, and her big sister unhappy. Consequently, she has as much faith in men as she does in sparkly flying ponies. She welcomes attention but is wary of anything else. I'm the bigger slut and the bigger romantic, while she, who has "waited," is infinitely skeptical. The irony of our living together is neither wasted on nor particularly interesting to me.
    "Really?" I ask her in the cab. "Not one dick? What about that guy in that band . . . "
    Lili looks out the window at the Bowery speeding by. "He just took it out and was like, 'Can you touch it?' and I just sort of looked away and," she makes a swatting motion, "I think that was why he left."
    "They're not that bad," I say. "I'll draw you pictures at home."
    When we get home, I get out a piece of yellow construction paper — which I was using earlier to cut out autumn leaves to decorate the living room in bucolic fashion — and draw penises, circumcised and uncircumcised in both erect and flaccid states, explaining the mechanism to Lili. "You know…" I say, without looking up from my drawing, "Rusty has a nice one. You should have dealings with it."

    "But if it's my first, and it's nice, won't the bar be set too high?"
    "That's not how it works," I assert. I hand her the diagram. Lili folds it and puts it in her purse.
    Meanwhile, starting with Rusty's first night in town, I constantly ask him things like, "Doesn't Lili look nice today?" and "Wouldn't you like to have sex with my roommate?"
    He assents to both.
    Nothing happens, though. They're both busy and have, you know, free will. Despite my Marquise de Merteuil-esque manipulations (which I'm actually pretty bad at because I keep getting drunk with my pawns), they don't hook up.
    Then suddenly, sadly, it's Rusty's last night in the city. He's out watching a friend's band. Meanwhile, I'm out with Lili, Jemma and Kate (our friends from London who are crashing with us) and my boyfriend Jack (my boyfriend? another story). At one point, in one crowded bar, Jack and I are amused by girls fending off would-be suitors. One tries tapping Lili on the shoulder until she gestures at the television, which is playing Lord of the Rings with no sound. "I'm sorry, but could you stop?" she sighs in his face. "It's my favorite part."
     After this incident, Lili turns to me. "I think we should go."
    "Okay," I say. "I'll get my coat."
    She stares at the floor, unmoving. "And I think I love Rusty."
    YES! SCORE!
    "That's cool," I reply casually. "Maybe he'll show up later."
    Then we're outside. As everyone else is walking east, I lag behind a little, frantically text-messaging Rusty: "Lili loves you! COME OUT!"
    Our group congregates in another bar. When Rusty shows up, Lili's sulking because she's tired, and we can't get free drinks. I'm on Jack's lap, stroking her hair and trying to console her.
    "Sweetie, maybe if you didn't tell the bartender you hated him, things would be working out better. Rusty!" I exclaim, jumping up to hug him. Buy Lili a drink, I whisper. Whiskey and coke. Of course he does, and of course this endears him to Lili, and before you know it, they're chatting away in a corner, touching each other on the shoulder.
    Then Rusty comes over to me, looking disconcerted. "Lili spilled her drink on me. On purpose."
    I'm not entirely surprised.
    "I think it's terribly sweet," interjects Kate, who knows that she and Jemma have a whole futon to themselves if Rusty ends up crashing in Lili's room. In fact, I'm kind of terrified about what the sleeping arrangements will be if he doesn't. There's me and Jack and Lili and Rusty and Jemma and Kate, and Kate's hanging on some guy, and I don't think any of these other people are planning to crash, but you can never be sure. My apartment is maybe 350 square feet, total. Sometimes I wake up, survey my living room and think of epic Viking war poems that talk about the ground being covered thick as snow with bodies.
    With this in mind, I head home with Jack to secure our places in my bed. It should, I guess, be the precursor to all sorts of exciting things. Instead, I'm out when my head hits the pillow, and I only wake up when Rusty knocks on my door the next morning.
    "Brunch? I've gotta leave for the airport in like an hour." I dress and tell Jack I'll be back soon, and as Rusty and I head out I note that the futon is occupied by Jemma and Kate.
    We sit down at a café on my block. It's a place I've never been before ­ always seemed kind of antiseptic, lots 1950s colors and Lucite. Our block is famous for restaurants, but Lili and I conscientiously object to all but four of them: the Dominican place on the corner, the tapas bar with the pretty garden, the quiet fancy place we went for my birthday, and the café at the end of the street. Incredibly, this leaves another six or seven assorted bistros, sake lounges and wine bars.
    "So you and Lili . . . ?" I ask Rusty, eyebrows raised.
    He sighs. "She's a funny girl."
    "You get any play?"
    "We kissed a lot. She's a good kisser."
    I try to remain casual. "What makes a good kisser?" (Translation: Was I?)
    "Aggressive, not sloppy. Soft lips."
    "Oh, was that it?" (Fuck. I think I'm out of Chapstick.)

    " I got her to take off her shirt. Then she was like, 'This isn't working for me.' Then she decided she didn't like the shirt she had on before and she spent a while looking for a new one."
     He sounds a little annoyed. The rest of brunch is spent on random conversation, on saying how nice it was to see each other, on this, on that, and when I hug him goodbye and watch him catch a taxi I'm really distraught, enough so that Jack notices it when I get back in bed. He's face down, just shoulders and the back of a curly, dark head, but I guess he can see that I'm curled in the far corner of the bed, biting my knee. I should probably lie down on his arm, try to be next to him, but I don't really feel like lying next to anyone right now. That wouldn't fix anything.
    "What's wrong?" he mumbles .
    "Nothing," I say, a little too quickly. "He's my friend. And now he's gone. It sucks." I don't know what I'm so put out about, aside from the fact that until brunch this morning, most of my conversations with Rusty had some hook-up-with-my-roommate pretense, that I had to waste my limited time with him like that.
    Then Lili comes into my room and sits on the edge of the bed. "Wanna get brunch soon?"
    "I can do brunch twice." This is a fact.
    "Did you already go with Rusty? Is he gone? Shit, I should've said bye." She sounds distant, but not too upset.
    "Yeah. How was all that?"
     "He was nice. Cute. Boyslut, though. More your type than mine."
    Then, even as I sulked, regretting my pettiness and time lost, I started to feel better, because I knew I'd see Rusty again — here, in Chicago, wherever. This is the paradox of the Cool Ex. I created a superficial friendship out of tense joking and studied flippancy, to overcompensate for post-hookup awkwardness, as a way to bridge that initial discomfort. But once it was bridged, I had — surprise — an actual, real live friend. Which is important. There are people I can talk with about whiskey, there are people I can talk with about Gram Parsons, and there are people I can talk with about being a slut, but all three? That's special. n°