I Was Friends With My Boss — Then Things Got Weird

When Tiffany*, 33, started working as a social media director at a start-up in Washington DC, she immediately clicked with her boss (who we’ll call Layla). Layla was friendly and funny, and both women bonded about being women of colour in the workplace. “She sort of lit up the room when she walked in, her energy was electric,” Tiffany told Refinery29. But soon, Layla’s behaviour started to make Tiffany uneasy.
A few weeks after Tiffany started, Layla began to call her after hours to vent — “first [it was] about work, then it became personal.” Tiffany said. Initially, Tiffany was open to engaging in the conversations as she wanted to impress her new boss, but she quickly started to feel uncomfortable. “I realised she was often calling me to gossip about her bosses or employees she hated,” Tiffany said. “Once she even called me to tell me she was overwhelmed with trying to figure out a way to push some of [her] peers out of the company.” Before too long, Tiffany realised something wasn’t right.
Like Tiffany, many professionals have found themselves wanting to develop a connection with their boss — but building a bond with your supervisor can be tricky. On one hand, a strong relationship with a boss can be a foundational career investment and contribute to better communication and collaboration. On the other hand, blurred boundaries between professional relationships and personal friendships can quickly get complicated. Given the fine line separating the two, an important question arises: How close is too close?
Olivet Nazarene University recently set out to identify the new norms of boss-employee relationships in the US. The survey of 3,000 people found that one in three workers had had a boss ask for personal advice, one in four of those surveyed had hung out with their manager socially, and one in 20 said they were connected to their boss on Instagram or Snapchat. And while the survey found that certain levels of intimacy with a boss — such as meeting their child or significant other — can actually correlate with worker happiness, this isn’t always the case.
Jillian*, 29, quickly struck up a friendship with her boss at her tech company in Austin, Texas. The two women were similar in age and, from the beginning, her boss tried to get to know Jillian and the rest of her teammates. “She often invited [us] to her house for social events like holiday parties, and team meals,” Jillian told Refinery29.

There were times where she would be working from home and take a video conference call while sitting in bed, with her partner [sleeping] shirtless next to her.

But over the course of Jillian's one-on-one meetings, her boss began to share about her past queer relationships. Jillian, who identifies as queer, found this to be an uncomfortable topic to discuss with a new supervisor. "It was as if she was trying to bond over [our] shared queerness," she said. And this wasn’t the only time Jillian was made to feel uneasy by her boss’ behaviour: “There were times where she would be working from home and take a video conference call while sitting in bed, with her partner [sleeping] shirtless next to her,” said Jillian.
Though Jillian and Tiffany’s experiences with their bosses weren’t entirely positive, some relationships of this nature are. Abby, 29, ended up developing a very close relationship with her boss while working as a senior account executive at a PR agency. The two would go on vacations together and brunch on the weekends, and acted as each other’s sounding boards for both personal and professional challenges. Abby owed this closeness to the non-hierarchical culture at her company, adding that the two made sure to set clear boundaries — "there [was] an understanding that [our] friendship does not affect work."
According to Abby, the relationship with her boss enhanced her ability to work productively and effectively. “While for some people, there can be such a thing as ‘too close,’ it never felt that way for me,” Abby told Refinery29. She added that the two were honest, transparent, and respectful with one another — “just as good friends should be.” Ultimately, Abby credits her friendship with her boss to her success in her role. “Our friendship allowed us to work better together, and ultimately, drove better results for the projects we managed together.”
Defining what constitutes an appropriate or inappropriate relationship with a boss varies from person to person. “[The relationship] is okay as long as both parties feel comfortable,” says Ariel Schur, LCSW is the CEO and founder of ABS Staffing Solutions. Ariel started her career as an Employee Assistance Program counsellor for employees of Fortune 500 companies — and she admits she, too, once became friends with a former boss.
Though Ariel’s relationship with her boss was healthy, she acknowledges that befriending your supervisor can be tricky territory. “Some people might feel that their boss is contacting them too often, which could be distracting if you are looking to shut off for the night post work,” Ariel told Refinery29. “Being friends with your boss on social media can also be tricky — you don't necessarily want your boss knowing your weekend plans or where you went after work.”
For this reason, Ariel recommends reflecting on the type of relationship dynamic you might feel comfortable with — and being very clear about your limits from the beginning. “Unless you set forth very clear boundaries and make a concerted effort to adhere to them, it’s very easy to cross lines,” Ariel said, acknowledging that as people spend more time at work, these lines between the personal and professional can easily blur. “We spend [over] 40 hours a week at our desk, so it's natural to want to have a sense of closeness with your boss.”

Unless you set forth very clear boundaries and make a concerted effort to adhere to them, it's very easy to cross lines.

While boundary setting is always a good idea, Ariel also recommends listening to your intuition. “If something feels off, don't ignore the uncomfortable feeling,” she said. If a relationship or dynamic veers into dangerous or uncomfortable territory, say something, she adds. “Don't be afraid to speak up, and don't allow yourself to feel like you 'deserved' it in any way.”
Tiffany’s troubled dynamics were resolved after her boss was transferred to a new location after several employees reported her for inappropriate behaviour. And though the situation was settled, it left a lasting impression on her. “I realised it’s naïve to assume that just because [your] boss is ‘cool’ or looks like you means they will be supportive, professional, [or] a good mentor,” Tiffany said. “I’ve learned that the goal is not to be your boss’s pet — [it’s] to be the best at what you do and earn the respect of your team.”
As for Jillian, she was abruptly let go after her tech company had a large layoff. And though she is currently out of work, she says her experiences with her old boss are helping her in her job search. “I’m ensuring I look out for some of these signs in future bosses as I interview for new jobs,” Jillian said. “I am learning that it's important to trust my gut — if something seems 'off' there's usually a good reason for it.”