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Should You Ever Become Friends With Your Boss?

Yes, but also, only kinda, but maybe for real if you set some boundaries, but that’s really hard, and shit, sounds like this really isn’t going to work

Nowadays, most companies are more casual than ever before, which for the topic at hand, means maintaining a strictly professional relationship with the higher-ups is more difficult than ever. When the average workday involves happy-hour cocktails and late-night shop talk/gossip on Slack, forming a bond of some sort with your boss (and potentially even their boss) is basically inevitable. But no matter how chill your superior (and again, their superior) may be, there are several considerations you should make before becoming all buddy-buddy.

Sure, befriending your boss comes with some benefits. As we previously reported, “Being close to the boss gives you greater access to the most important decision-maker in the company, and a chance to make you and your work a top priority in the organization.” There’s also the possibility that being friends will improve your workflow and make the average workday more relaxing, since a friendly boss — one who knows you well on a personal level — should theoretically make you less anxious than an overbearing one who simply wants you to get shit done as fast as humanly possible.

Plus, making new friends is always nice (especially for men, who typically have few friends after they turn 30), and for many people, long hours might mean they have trouble meeting people outside of work. “Some of the best and longest friendships I’ve ever had have come from work,” commenter Forestman88 writes in a related Reddit thread (sic). “You just be careful who you open up to — don’t talk about that great sex party last weekend or how you’re trying to pass the next corporate drug test.”

Ethical or otherwise, forming a relationship — perhaps one that’s more than just collegial — with your boss might also result in a promotion. “She sat on my face, and I got three more bucks an hour to lifeguard the local pool,” commenter d-boy5050 writes in a thread about sleeping with your superiors (sic). “It was the best summer job I ever had.”

Commenter brilliantbarnacle had a similar positive experience (once again, sic throughout). “I slept with my boss, got a raise and now I’m married to him. It was a good life choice.” It’s worth noting here, though, that many companies have policies to prevent romantic relationships between superiors and their direct reports. For good reason, too: That way, a boss can’t change the course of someone’s career — either in a good or bad way — simply because of their romance.

Speaking of shit going bad, that’s really the most perilous aspect of becoming BFFs with your boss. “Honestly, it’s tricky,” says career strategist Daisy Swan. “It’s like going to an interview: Even though people are dressed casually, you still need to be a professional.” Not to mention, the other people in your office obviously might not appreciate the close relationship you have with the boss. “It creates power dynamics in the organization that are viewed as nepotism, favoritism or discrimination,” says HR expert Jennifer Longnion.

Furthermore, Swan warns that befriending your boss can end up sticking you with even more responsibilities. “You don’t want to get into a codependent relationship and feel like you’re responsible for things you’re really not responsible for,” she explains. “I’ve worked with many clients whose bosses have come to rely on them so much, and then my clients feel like they can’t leave — they get kinda sucked in.”

Now, a lot of this depends on the company. “It isn’t a one-size-fits-all approach,” Longnion confirms. “Some companies are family-owned and inherently have spouses who run them together, or moms, dads, kids, uncles and aunts.” Perhaps then, smaller companies, with fewer people involved, are safer places to test the friendship waters with your boss.

Another positive: Swan and Longnion agree that, no matter where you work, you can still be friends with your boss — so long as you set some ground rules first. “Both parties just need to realize that, when it comes to the business, the leader has to make decisions and calls that are objective, fair and impartial for the benefit of the organization or business as a whole. The friendship isn’t the priority when it comes to work.”

As for anything beyond a friendship, while it might work out in some cases (congrats on the $3 raise, lifeguard dude), as we learned while interviewing three guys who slept with their bosses, shit usually hits the fan at some point. So I’d highly recommend not fucking the person who manages you. I also, though, wouldn’t get overconfident even if you just remain friends, with the old mantra “hoping for the best, but preparing for the worst” probably being the most appropriate words to live by.

In other words: You’ve been warned, buddy.