Packing Up Is Hard to Do

Photo: Illustration by Zohar Lazar

In the world of relationships, there are two big no-no’s: dating your friend’s ex and dating your roommate. Though the first is more evil, it can only leave you friendless—while room-mating just might leave you homeless. Yet some people, no matter how well they know the risks, can’t avoid doing their courting in reverse: moving in, then falling in love.

This summer, Deirdre Wilson, 26, who works at a sports club, found herself in need of a roommate in her Upper West Side two-bedroom. A male friend suggested his brother Sam, who was moving to the city from the Midwest. She had reservations about living with a man but figured she would meet him. “The brother introduced us,” she recalls, “and said, ‘Are you attracted to her? Are you attracted to him? If so, do not under any circumstances move in together.’ Sam was short and fat, so I said, ‘No problem.’ ”

He moved in, and they got along well—a little too well. “Within a month, everybody was saying, ‘You guys are so great together,’ ” Deirdre says. “Even my mother thought it was going to happen. The allure of everybody saying that, combined with the pressure not to, led us to do it.”

It didn’t bother her that he was unattractive; as any seasoned single girl knows, those guys get all the women, because women assume they won’t cheat. The sex wasn’t good the first time, but she liked him so much that it didn’t stop her. Over the next four months, as they kept dating, Sam began treating Deirdre more like a girlfriend than like a roommate, picking her up from work, asking her to make dinner.

But the ho-hum sex was a downer, she says, and they decided to be no more than friends. Which wasn’t so easy given the fact that they were already living together. A week after the “breakup,” Sam asked her, “So are we dating other people?” She said he could, but she didn’t want to hear about it: “He said, ‘But I want to share the details with you,’ and later I found out that he was dating someone in the same building.” Haunted by visions of Sam’s bringing the woman home while they were still sharing the apartment, Deirdre decided they should both give up their lease. She’s now living with her parents, and Sam’s going back to the building to date their old neighbor.

“If Alex and Justine’s dating wasbad for their roommates, being roommates was just as badfor their dating.”

Alex Stark, 24, is another room-mater. An attractive guy who resembles a young Ben Affleck, he was living until recently in a Dumbo loft with three male friends. Then one roommate decided to move to L.A. to become a screenwriter. The others began interviewing prospective replacements and got a call from a young painter named Justine. Alex liked her as soon as he met her—she was slim and curvy and, more important, artistic. “It was a combination of thinking she was cute and thinking she’d be good for the loft,” he says.

For not solely altruistic reasons, he threw himself into easing her transition—like helping her find a cheap bed store. “She was everything I wanted in a roommate,” he recalls. “She was cleaner than the guys. She baked pies. We got to know each other by doing projects—we hung lights together, bought plants. Thinking about what the house could become with Justine and I running the show was exciting to me.”

One night, he went out to an Amsterdam Avenue bar with Justine and some friends. They felt a mutual chemistry, and they split a cab home: “The night was unbelievably romantic and perfect. And the best part was that neither of us needed to invite the other one back.”

Their roommates weren’t happy they were hooking up, so he and Justine tiptoed around more than they wanted to—Alex would go to sleep in his bed and emerge in the morning from Justine’s. (Eventually, they agreed the cheap bed wasn’t working.) If their dating was bad for the roommates, being roommates was just as bad for the dating. “It was kind of a slight when I’d say, ‘I think I want to sleep alone tonight,’ ” says Alex. “When you take away the whole ‘I don’t want to get on the subway and go all the way over’ conversation, saying you want to sleep alone sounds a little insensitive.”

But at the same time, he liked the intensity. “When you’re dating your roommate,” he says, “the relationship is accelerated. Right away, you get to see what they look like in the morning and what kind of TV they watch at 4 a.m. And there’s this lovely rationalization that says, ‘Go as fast as you can, because if you’re not suited for one another, you might as well find out sooner rather than later.’ ”

When he returned from a summer trip to Europe, things weren’t the same. The connection wasn’t there—and what’s more, the place that he and Justine had once so enthusiastically cared for together had gotten messy, which depressed him. Telling himself that it might save the relationship, he decided to move out—even though he’d been there first. “I realized the relationship had to some extent been about convenience,” he says, “and I wanted the perspective to see if we really had a shot at staying together.”

He quickly found a place in the East Village with two roommates, a guy and a girl. As soon as he moved in, it was as though a weight had been lifted. He felt free and single, even if he wasn’t. “Once I moved into my new place,” he explains, “I was faced with the logistical possibility of bringing someone else home, which was never a prospect when I was living with Justine.”

A few weeks later, he and Justine broke up. There’s just one problem: Lately he’s been thinking his new roommate is pretty cute.

Packing Up Is Hard to Do