Help! I Fell Out With My Work Bestie

At 22, Chloe was living every fashion girl’s dream. Months after graduating from college, she walked into the shiny office of a magazine to interview for a job that a million girls would kill for. And unlike The Devil Wears Prada’s cerulean-sweatered Andy Sachs, she sailed through it. In fact, Chloe’s soon-to-be boss told her that she reminded her of her younger self, partly because — wait for it — they were “two private school girls.” (She even cracked an in-joke about taking Latin class.) “I was like: ‘Whoa, this is a cool, radical boss-and-employee relationship,’” Chloe tells me, remembering a rush of acceptance. But now? “I see that there is no such thing.”

At first, Chloe, whose name has been changed, and her editor, whom we’ll call Julia, became fast friends. Julia acted more like a big sister than a boss, as if they were “in this together,” against the male-dominated, cutthroat media world. But over time, as their bond strengthened, the boundaries between them evaporated, and Chloe says she eventually realized Julia was “lonely, power-hungry, and deluded.” When the two were in Friendship Mode, Julia would talk badly about their colleagues, even revealing private information. And at work, Julia would share detailed, graphic descriptions of her sex life. “She’d be telling about whatever crazy sex thing she and her husband did,” Chloe says, “and then she’d be like, ‘Right, time for the pay review!’” Their relationship hit an all-time low at an industry event, where, bizarrely, Julia tried to physically force her junior employee to eat chocolate — a food Chloe had never liked. “She took a truffle and said something like, ‘Go on, for once, eat chocolate!’ then shoved it on my closed mouth then dragged it down my silk dress.” As Chloe desperately tried to save her stained dress in the bathroom, she wondered if, at this point, it was even possible to introduce boundaries here without committing career suicide.

We spend about a third of our adult life at work, so it’s no surprise that workplaces are a breeding ground for intense friendships. According to one poll, 82% of American workers have at least one colleague they consider a friend. However, only 15% are considered “real friends” — a distinction that leaves plenty of space for confusion. When you consider office politics, which can spark feelings of jealousy and competition, alongside unequal power (not to mention pay!), then maintaining these friendships can often feel like a job in itself. Really, it doesn’t take much for a “work bestie” to become a “work nemesis” — and the fallout can be even messier than chocolate on a silk dress.

Earlier this year, like any self-respecting millennial, I recently read Lena Dunham’s memoir Famesick. Out of all the stories she shared (and overshared), I was most captivated by her description of the Girls co-showrunner, Jenni Konner. Dunham characterises Konner, who is 15 years her senior, as an amalgamation of boss, mentor, and BFF. In the book, she comes across as the quintessential “cool girl,” whose approval Dunham craved to the point where a single awkward interaction or sideways glance could ruin her day. After Girls wrapped, Dunham claims that Konner pressured her into accepting less money in an overall deal with HBO, so the producing partners could have pay parity — a big ask, given that only Dunham was a household name. Gradually, as they attempted to run a production company together, their relationship became strained. And by 2018, Konner and Dunham ended up in couples therapy, where they agreed to sever all ties.

These types of tensions don’t just happen in Hollywood, because they’re never far from the surface in everyday work settings. Mark, a government communications specialist, tells me he also had a friendship-ruining fallout with his mentor at work. Last year, when the 30-year-old started a new position, he became fast friends with the manager who trained him for the role. After being taken under her wing, the pair became close, especially because they were the only “out” queer people on the team. But a few months later, Mark noticed his new boss becoming short, dismissive, and condescending — a vibe shift that made him pull away. “She seemed to pick up on this as she became noticeably nicer to me, which made me lower my guard and trust her again,” he says. “But soon after, the ‘old her’ returned, and I realized I’d been tricked.”

“The funny thing was, she wore a ‘Be Kind’ badge on her lanyard, despite being one of the most horrible people I’ve ever had the displeasure of working with!”

Looking back, Mark says it was “very odd” to go “from work besties to arch nemeses” in such a quick timespan. Now that he’s moved on, he wishes that he had confronted her about it, but he chose not to because she had power over him. Even outside of a mentor-mentee relationship, the same concern often applies: Is getting closure or clarity about a rift really worth potentially blowing up the relationship further?

In the end, Mark never got to the bottom of what went wrong. “My biggest hunch is that because I was the youngest and newest person on the team, she probably resented me in some way,” he says. “The funny thing was, she wore a ‘Be Kind’ badge on her lanyard, despite being one of the most horrible people I’ve ever had the displeasure of working with!”

Psychologist Ian MacRae — author of several books on the psychology of the workplace, including Myths of Work — tells me that the intensity of work friendships mostly stems from the proximity of seeing so much of each other, either in person or on Teams. And it’s also about the “unwritten rules” of the workplace, where a clear structure and expectations of behavior can actually make building relationships easier than in the outside world. When you add in the shared experiences colleagues develop, especially in high-pressure environments, then you’ve got a fast-track for accelerated friendships.

What makes it so tricky, though, is that friendship often involves conflict. And while the rules of the workplace make it easier to bond initially, they can hold you back from resolving or repairing disputes in a way that you would with an out-of-office friend. “If there’s an unequal power relationship where you don’t feel like you can say what you want to say, or there’s consequences for saying certain things,” MacRae explains, “then resolving the conflict may lead to other problems.” (It’s also worth noting that, while you might think you and a colleague are on totally equal footing, there may be subtler seniority differences or other softer power dynamics at play.)

In theory, managers are supposed to be responsible for maintaining clear boundaries and healthy communication, but in reality, it often falls on their underlings, who contort themselves around their boss’s needs. So if you’re in Mark or Chloe’s position — contemplating whether to confront a manager — what should you do? “Be really clear for yourself on why you’re at that job,” MacRae advises. “You have to ask yourself the question: Is this worth dealing with? How long do I want to be here? Is the relationship something that I want to try and resolve? Because sometimes, if you try to confront it, it can lead to an unending nightmare.”

“She seemed to pick up on [the tension] as she became noticeably nicer to me, which made me lower my guard and trust her again. But soon after, the ‘old her’ returned, and I realized I’d been tricked.”

Work relationships can get even more complicated when they transcend office walls. In my own professional life, I’ve been surprised (read: horrified) to discover just how many people decide to move in with their colleagues, which perhaps speaks to just how enmeshed work is in our personal and social lives. When Henry, 39, was working at a prestigious publishing house in London, he became very good friends with one of the other editorial assistants. Over the next four years, they were inseparable, fully transitioning from “work friends” to what he calls “real friends.” When the pair moved in together, things changed when Henry quickly realized that, at work, they hadn’t actually worked very closely together and their friendship mostly consisted of “bitching about other colleagues.” But at home? “I found him very, very difficult to deal with,” Henry says. The sassiness and bitchiness that made him entertaining at work, it turns out, were nowhere near as palatable outside of the office walls.

Something similar happened to Kyle — not his real name — a 27-year-old American who moved to London in 2020 to work in finance. As he settled into his new life, he quickly scored not one but two besties, who were also at the bottom of the corporate ladder and working long hours. These young women weren’t merely friends, but they became Kyle’s support system, who he confided in about his family life, his sexuality, and mental health. But when the three of them moved in together, their lifestyles weren’t compatible at all. Kyle didn’t drink or smoke weed, but his new roommates were living for the weekend and wanted to spend their time off partying. Gradually, he was cut out of social plans, with the girls becoming a separate clique. “I was part of the in-crowd,” he remembers, “and then, all of a sudden, I was out.”

Eventually, Kyle began to dread coming home from work to a frosty atmosphere. And at a particular low, he remembers having a “nervous breakdown” and crying in his room. To make matters worse, when he decided to move out, the roommates had a huge, raucous party the night before he left — even though they knew he had to wake up early the next morning to move out. Looking back, Kyle was struck by how different his friends behaved outside of the office. “One of them, who in fairness was probably the nicest to me, would present this image outside the house as this pristine posh girl,” he says. “But at home, she was so messy — she would pile her dishes in the kitchen for days until they stank.”

The fact that people often present different versions of themselves at work — whether as a deliberate strategy or subconsciously — makes taking the leap from office bestie to roommates very risky. Psychologists Hazel Markus and Elissa Wurf identified the phenomenon in 1987, which they describe as the “working self-concept” — a subset of “self-knowledge and beliefs” that can influence our behavior in different social situations as we navigate work, family, friendship, and romance. MacRae says that, in the workplace, there are a lot of rules that are often outside of our control, whereas “once you start living with someone and it’s their own environment, where they’re setting their own rules, it can be totally different.” He thinks the gulf in expectations between the home and the workplace “can be the biggest, broadest difference in how people act,” which can totally upend a friendship.

Such an immediate shift in dynamics can swing the other way, too, if a personal relationship becomes a professional one. In 2012, Mario, 39, accompanied his cousin on a work night out and immediately hit it off with her boss. In a strange turn of events, he was offered a job as an assistant and accepted it on the spot. As cousins, they had been thick as thieves, but as co-workers? He found her to be a “lazy, conniving” manipulator, who exhibited “weird, micromanaging” traits. “She would act like she was my boss — she wasn’t. She would work 9 a.m. to 2 p.m. — just ‘cause she felt like it — when I would work 8 a.m. to 5 p.m.,” he remembers. “She was a complete terror as a co-worker.” When the pair were both executive assistants, Mario used to joke: “This is The Devil Wears Prada, except the co-assistant is the ‘devil’ — and she wears Walmart.”

Another major point of contention was that, during their time working together, Mario’s cousin began cheating on her husband, who he knew, and even had the new guy pick her up from work. Switching back to “cousin mode,” she swore him to secrecy, and when he told her this made him “very uncomfortable,” she totally lost it. After three years working together, they had their biggest-ever fight — a screaming, reality-TV-style showdown in the hallway. Mario left soon after that and, 10 years on, the pair still don’t speak or socialize.

“You have to ask yourself the question: Is this worth dealing with? Because sometimes, if you try to confront it, it can lead to an unending nightmare.”

On the topic of family, a wider culture shift over the last decade is the “family-fication” of work. When BuzzFeed-era millennials joined the workforce, they embraced the HR-infused language of workplaces referring to employees as “a family” — rather than a group of people who are exchanging labor for money — with particular enthusiasm. (And there’s a simple reason why our corporate overlords might encourage this: because research suggests such tight bonds can be productive and profitable and engender loyalty.) The problem is that, according to a “Having Workplace Friends Is Not Always Fun,” a 2019 study by German academic Sabine Hommelhoff, our expectations of these relationships are vastly different. From friends and family, we want loyalty, support, and sympathy, but the workplace normalizes criticism, accountability, and competition.

Looking back, Chloe thinks this family-style approach underpinned the culture at the magazine where she worked, which she can now see was basically Deloitte with “nicer clothes and less money.” She compares her relationship with her editor, Julia — the quintessential millennial girlboss, who was encased in a web of corporate contradictions — to ChatGPT, which affirms users with positive responses. “She hired a group of sassy, opinionated, sometimes bitchy, sometimes judgmental women,” she explains, “but you have to know that, if you are someone’s boss, you are going to be getting this ChatGPT-style response from them.” Years later, she can see that her boss wasn’t a bad person — she was just someone who didn’t realize that she “actually had power over” the people she considered friends. In reality, the organizational hierarchy meant their relationship was built on deference, even when she did outlandish things.

As with other friendship breakups, there can be a deep sense of loss when office friendships don’t sustain themselves outside their initial setting. Over my entire decade-plus working life, there are only two colleagues I’ve managed to hold onto as close friends, which makes me doubt whether the other friendships were as “real” as they seemed when we were trauma-bonding over a boss from hell. Reading Famesick, I got the feeling that Dunham still hasn’t quite worked out what her relationship with Konner really was. (And it’s notable that it went south pretty quickly after Girls wrapped.)

MacRae, the psychologist, thinks a lot of people make the mistake of not seeing these friendships as two very separate entities: a workplace relationship and a friendship. This distinction is why it can feel so jarring when you stop working with someone and the friendship fades too, as there’s an entire half of the relationship that wasn’t properly resolved. Still, even when work friendships fizzle out (or implode), they can still be valuable learning experiences. Kyle says moving in with his colleagues has taught him about the dangers of gossiping, because he spent a lot of time listening to his former work besties talking behind each other’s backs without realizing they were probably doing that to him, too. Mario wishes he’d handled his beef with his cousin “like a co-worker” rather than a family member. Now that he’s older and has gone to therapy, he’d approach it totally differently. Chloe regrets ghosting Julia when she left the company (even if Julia later blocked most of the team on Instagram).

And Henry is a rare example of someone who managed to find a way back from the abyss. After his disastrous move-in with his sassy co-worker, they stopped speaking for a few years, only to eventually find their way back into each other’s lives in a “softer,” less intense way. They even managed to talk constructively about what went wrong. It goes to show that an office bestie-turned-nemesis can still become a “real” friend — you’ve just got to put in the work.