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‘My Boss Wants to Be My BFF, and It’s Making Me Uncomfortable’

Illustration: The Cut

Dear Boss,
I started a new job around the time COVID-19 hit. I moved about six hours away from home to take the job, so I was starting over in a new city where I didn’t know anyone (aside from a few friends-of-friends). I worked in the new city for a month, but, when everything shut down, I returned to my hometown to work remotely as I wanted to be closer to my family and friends.
My new boss, Janet, is really kind, but she keeps mentioning that, when I come back, we should hang out outside of work and she could show me around the city. At first, I thought this was a good idea because I wasn’t familiar with the city and it would be a way to meet new people. But she keeps bringing it up (“when you come back, we can go hiking, check out parks, etc.”). She has mentioned “hanging out” almost every week since we started working from home months ago. It’s making me really uncomfortable, and I’m unsure how to respond. 
Janet is a first-time manager. I’m a woman in my late twenties, and she is twenty years older than me. We are both administrative staffers and the only two people in our office who perform our duties. She has been at the company for almost 25 years and has mentioned she becomes “attached” to people and gets emotional when someone leaves the department, even if they are retiring or moving away.
I’ve always felt there should be boundaries between managers and employees, so these constant messages make me uncomfortable. I am a shy person, and I would prefer to open up to people on my own terms, without the poking and prodding. I did have a really good relationship with my boss at my old company, but we wouldn’t spend time outside of work with each other. Mainly we would grab coffee during the workday and walk for a bit, or sit and chat. We still keep in contact, but we have never hung out socially.
Janet has offered to help me get set up in my new apartment when I return (even though I’ve mentioned that my parents and siblings will be helping me). She also frequently says things like, “I will be there for you as a friend” when I complete everyday tasks. 
I feel guilty saying it, but these messages are getting out of hand. Janet genuinely seems like a kind person, but it makes me anxious whenever she brings it up. I am scared to appear rude and tell her that I want to figure out the city myself, alone. I am — in some ways — dreading moving back, even though I was super-excited before.
How can I navigate this awkwardness? I don’t want to appear chilly or unpleasant, but, at the same time, I want to have a good work/life balance and do my own thing, without having my boss in my personal life.

Very little is more awkward than a boss who wants a closer friendship than you do. The power dynamics involved can make it tricky to set the boundaries you want because you naturally worry about offending the person who has so much control over your income and your professional success.

That, of course, is exactly why it’s so inappropriate for managers to do this — the power disparity means many people won’t feel comfortable turning down social overtures they’re not interested in, and there’s a strong financial incentive not to risk casting a chill on the relationship. Plus, even if you were open to socializing, friendships between managers and employees are fraught with problems: Your manager’s job is to judge your work, so you’re inherently on unequal footing. It’s hard to receive critical feedback from someone who you got drinks with the night before (it’s hard to give it in that situation too). Your manager will need to make decisions you might not be happy with and could even need to fire or lay you off one day. And even if, somehow, you both navigate this well, people around you will assume there’s favoritism in play — whether or not there really is. It’s bad for both of you.

That’s not to say that managers and employees can’t have warm, even affectionate relationships. They can. But there’s a difference between friendly and friends, and effective managers stay on the right side of that boundary, at least until you’re no longer working together.

So what can you do when you have a manager who’s oblivious to all this? Well, the good news is that, as long as you’re remote, any plans Janet alludes to are purely hypothetical. But if she continues pressing you to hang out once you’re back in the office, you’ll probably need to address it pretty straightforwardly. If she weren’t quite so persistent, you might be able to get away with having other plans whenever she invited you somewhere. And you can still try that if you want. There’s no reason you can’t allude to a much busier life once you’re back; mention you’ve been getting to know those friends of friends, or joining a book club, or volunteering, or whatever will plausibly allow you to claim other plans.

But, given how persistent she’s already been, you’re probably going to need to shut it down more definitively. The most direct way is to say something like, “You’re so kind to offer! I’m old-fashioned about boundaries with my boss when it comes to hanging out outside of work, but I’d love to grab coffee one afternoon this week if you have time.” The offer of coffee is a concession because it’s helpful to offer something you are up for in order to keep the exchange warm and to demonstrate what you do want the relationship to look like.

If she keeps pushing after that, lean into the “old-fashioned” explanation. That makes it about you rather than her, and you can say things like, “It’s been drilled into me to keep things professional with my boss. I hope you understand.”

Then there’s the matter of her odd “I will be there for you as a friend” comments when you’re just doing regular work projects. In theory, you could respond to those with something like, “You’ve been there for me as a boss, which is even better!” But it’s possible that, in combination with the discussion above, that will come across as too heavy-handed, like you’re hitting her over the head with a “WE ARE NOT FRIENDS” message. So you could choose to let those slide for now — block them out! pretend they’re not happening! — in favor of shutting down the part that’s more aggravating (and more immediately urgent).

That said, if she doesn’t let up, at some point you might need to have a more pointed conversation. If it gets to that point, you could say something like, “Janet, I’m so appreciative of you as a manager and as a colleague, and I really enjoy working with you. (This may or may not be true, but it’ll help to say it.) I feel strongly about not being friends with my manager while we’re working together. I can do a better job if I’m not navigating work dynamics and friendship dynamics at the same time. I hope you won’t take that personally; it’s just the way I work. And I want to work with you for a long time (this also may or may not be true), so I’m trying to be careful about preserving those boundaries.”

If you say this warmly and then continue to demonstrate warmth in work-appropriate ways — thanking her for some work advice, joking with her about a project, suggesting the occasional coffee, etc. — this will likely end up being fine. In fact, make a point of having a warm interaction with her within a few hours of this conversation as a sort of relationship reset.

You shouldn’t have to manage your boss’s emotions to this extent! It’s not fair that Janet is making you feel like you do, and she’s got some fundamental misconceptions about what managing should look like. But it’s not rude to set the boundaries you want, even with your boss.

Order Alison Green’s book Ask a Manager: Clueless Colleagues, Lunch-Stealing Bosses, and the Rest of Your Life at Work here. Got a question for her? Email Her advice column appears here every Tuesday.

‘My Boss Wants to Be My BFF, and It Makes Me Uncomfortable’