Your Boyfriend's Ex-Girlfriend: The Worst Person Ever?

I could write a disingenuous think piece about this situation: something along the lines of "What the Reaction to Kim Kardashian West's Selfie with Amber Rose Says About How We See Women's Relationships," where How We See Women's Relationships would be something along the lines of "catty, competitive, and bad!" However: All celebrity feuds are but durational performance art, and instances like the Kardashian/Rose selfie are not true human drama but rather brief glimpses into the inner workings of the farce. More interesting to me, as a catty, competitive, and bad woman, is what the photo reflects about the general atmosphere—a blend of mystery, legitimate curiosity, jealousy, benevolent pity, an unlikely but apparently Kim Kardashian–approved desire for you all to "just be friends and hang out!", and fear—surrounding a significant other's ex.

Is there any worse person than a person who dated a person you dated before you dated them? Of course there is, but in times of paranoia or insecurity or Instagram stalking, it can feel like the answer to this question is, "No. Murder her! Or at least slander her online!" To make matters worse, many exes have interesting names—not weird, but it's not something you would have thought of, is it?—and interesting jobs, or they have names and jobs that are completely unremarkable but become imbued with a ridiculousness that is itself ridiculous but nevertheless cannot be helped. Mara? What kind of person has that name, anyway? And is she better than I am?

Albeit less incendiary than the Kardashian/Rose selfie, these questions fuel Leanne Shapton's brilliantly titled 2006 graphic novel Was She Pretty?, which is being reissued this week by the Canadian publishing company Drawn & Quarterly. Like a certain kind of relationship, the book is memorable, but brief; it's comprised of line drawings that accompany short, Lydia Davis–esque narratives that evoke, mostly painfully, the anxiety of exes. Dream cameos, old photos, nausea, useful but upsetting boxes of tampons discovered under a new lover's sink—Shapton quietly plumbs all the familiar trappings of the guilty fascinations we develop with those who came before.

Watch: How One Matchmaker Changed Online Dating for Women Everywhere

"I feel bad for most of my boyfriend's ex-girlfriends, because they all seem really lonely and not that interesting," a 25-year-old woman named Blair* told me. "There is one exception, however: a woman that I irrationally hate, even though they never really dated. I think it's because he was originally hooking up with me and her at the same time? But also because she has a terrible personality and likes all of his Instagram photos to this day."

Gemini Ferrie, a love coach based in Los Angeles, says women often come into her office looking for help with their obsession with a partner's ex—though it's usually not the first issue they talk to her about. "Oftentimes it's not the first thing that they share because they're embarrassed—but I can relate because I was very, very jealous ages ago."

Fixating on a lover's past "comes from a place of deep, deep insecurity," Ferrie says. "It's not something wrong with the woman, but she hasn't learned to love herself or think of herself as worthy of the love that she wants, so she's constantly afraid that she's going to lose this relationship she has with her boyfriend because of her own insecurities, and she's projecting that insecurity onto the ex and wanting to know more about the ex. Am I as pretty or as hot or as good-hearted or as kind? Did he like her more than me? Does he still think of her?"

"My boyfriend has two recent ex-girlfriends, and I think the reason I'm obsessed with them is because he still talks to/is actively friends with both," Kathleen* told me. "And they're not girlfriends from like ten years ago—they're people he was in love with in the last three years, which I find extremely strange as I avoid my exes, especially recent ones, at all costs."

The internet makes this all a lot worse, of course. Whereas girlfriends and boyfriends of the past might have come upon ex information by way of stumbling upon a box of letters or asking their lover's friends sneaky questions, today you can just Google and find everything from bad blog posts the ex wrote while interning at a PR company in 2008 to photos of her hiding deep in the recesses of abandoned blogs. And, of course, there are the usual social media accounts. "I constantly stalk [my boyfriend's] ex-girlfriend's Twitter, to the point where I accidentally followed her, which was embarrassing," Kathleen said. "I decided to keep following her as a power move, but it got really brutal, and I had to mute. I hate that I stalk her online, but I don't think I would if I knew they weren't still friends."

As with, theoretically, Kim Kardashian and Amber Rose, ex awareness can have a happy ending. In Katie J.M. Baker's 2013 Jezebel essay "A Tale of Mutual Cyberstalking," Baker obsessively checks her own ex's new girlfriend's social media accounts—made easier by the fact that the new love was "an actor on a popular TV show"—only to realize, at a pleasant and long-coming meeting, that the new girlfriend had been cyberstalking Baker, too.

Sometimes, however, fascination extends beyond the realm of natural internet stalking into immoral snooping and… actual stalking. "One time, like three years into our relationship, the ex sent him a record with a note inside the sleeve that said both 'love' and 'xoxo'," Blair said. "My boyfriend, fearing that I would see the note and become irrationally inflamed with rage, tried to crinkle it up and throw it out undetected. He failed, by which I mean I dug it out of the trash."

Nora* is a 24-year-old gallerist living in Los Angeles who fell in love with her now-ex-boyfriend Matt almost as soon as they met. She says she quickly became interested in the women he'd dated before he met her, even though (or especially because) Matt never really told her about his past loves, beyond a casual mention here and there. "I'm a very, very, very jealous person, so I ended up finding it out via chitchatting with his friends and slyly getting names," Nora said.

When she found out that one of the women—who was, intimidatingly, much older and more experienced than Nora—worked at a library nearby, Nora started really getting into reading. "I started to go to the library every day to sort of observe her," she said. "Am I better? Those sorts of thoughts. I kind of struck up a friendship with her via the library. We were in very different social circles, and she wasn't friends with any of his friends, so she never really found out." (After a couple of months, Nora's interest in the ex "fizzled out," and she went to the library less and less.) When Nora was set to visit the country where another one of her boyfriend's exes was living, she contacted the ex—"a fucking awesome political activist"—and said that she'd like to meet up… without ever disclosing that they had a boyfriend in common.

"When I met up with her, we ended up spending two days hanging out," Nora said. "She knew that I knew Matt, but never knew the extent of my relationship with him, and I never told her. I thought maybe she'd tell me things about him that he wouldn't if she [didn't] know that I was dating him!" (The ex never really told Nora anything of interest.)

Not everyone suffers. One woman I spoke to said she didn't know any of her current boyfriend's ex-girlfriends' names; while this seems commendable, it is a life of low-grade torture that many women say they would not be able to deal with. (And the woman in question described herself as "like a detective, but without a clue" after resisting the urge to open a "box full of memories" she found in her boyfriend's closet.) Few women I interviewed seemed legitimately well adjusted in this arena. "Ignorance is bliss," Cassie* said. "Why do I need to project, compare, and obsess over this person? It doesn't affect my life now, and there is no point dwelling on the past." This seems wise, but I disagreed with Cassie's later claim that all she has in common with her husband's exes is "that we have had the same dick inside of us." After all, it makes sense that you would share many similarities with your romantic predecessors, particularly if your significant other has a "type."

And, as one particularly deft story in Was She Pretty? demonstrates, there's always the chance that the ex could return to her former place in your lover's life—that one lover might make good on the possibility, often noted in the heady throes of a breakup, that you guys might get back together someday. ("Sarah was Michael's ex-girlfriend for ten years," Shapton writes, "but would eventually be his wife.") During one college relationship, Allie* told me she experienced what many ex obsessers would consider a worst nightmare: She realized her boyfriend was masturbating to his ex's Myspace photos. Worse, Allie said, she came upon this information by nefarious means, so she couldn't necessarily confront her boyfriend about it; she had been looking at his browser history and noticed a disturbing back-and-forth pattern between porn sites and his ex's profile.

Eventually, however, Allie "exploded." "We laid it all out, and he got pissed at me for looking at his history (which he had every right to)," she said. "He said he still had feelings for her and always would but that he didn't want to break up."

"I think that's where the sickness set in," Allie continued. "There's this awful innate thing in women that makes us so competitive with men. I should have broken up with his sorry ass, but instead, I wanted to know everything about her and find all of her weaknesses and make them my strongest assets. I started looking at her photos almost daily—how she dresses and the content she was putting online—and comparing myself.

"I found myself starting to dress and act more like her, whether intentional or not," she continued. Allie's boyfriend eventually cheated on her with the ex in question.

Another woman, Laura*, had the opposite problem: She was obsessed with a boyfriend's ex because the ex had died during their relationship. "Whenever we talked about it, I felt insanely guilty, like I was intruding on a different part of his life," Laura said. "I never felt I measured up." They ultimately parted ways, with Laura feeling like she "never got over it."

When I ask Ferrie what is to be done with all these intense, unproductive emotions, her reply is mildly disappointing: that the only way to get over it is to improve your self-esteem. "I would like to think that [giving] advice is as simple as it sounds—but it's kind of like [talking to] a woman who wants to lose the last five pounds," Ferrie said. "You say, 'Just don't eat ice cream!' but that doesn't help—obviously there's some kind of underlying, unconscious pattern or belief that is making decisions for the woman, without her even knowing that something beyond her awareness is making decisions she doesn't even like. Until the woman becomes aware of the blind spot—what is driving the obsession to compare herself to the ex—nothing is going to help whatsoever." (Ferrie also surprised me by saying that quitting internet stalking cold turkey won't necessarily help.)

If you can't do it for yourself, though, you might consider doing it for the person you're so obsessed with—taking that "benevolent pity" route. "The exes aren't doing anything wrong," Allie, who is now in a happier and healthier relationship, pointed out. "Even if they're sad and thirsty."

*Names have been changed.