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Don’t Befriend Your Boss
It will only make your work life more difficult

It’s Friday afternoon, the end of a long day at the end of a long week. You’re already planning the delivery you’re going to order for dinner when your boss pokes her head over the top of your cubicle. She wants to know if you’d like to go for a drink at that cute place near the office, the one that has bocce ball.
On the one hand: No. You’re tired. Your couch is calling your name, and spending a few hours trying to stay on the right side of the line between schmoozing and ass-kissing is the emotional opposite of going home and sitting. On the other hand, you do actually like her, and being pals with the boss seems like it could only be a good career move. Do you go and attempt to strike up a friendship? Or does something about spending social time with your manager feel a bit odd?
I know I’ve found myself grappling with that uncertainty before — and research shows that plenty of other people have, too.
In a 2018 survey out of Olivet Nazarene University, researchers surveyed 3,000 people with full-time jobs across 21 industries and found that the area between a strictly business relationship and a friendship was well-populated: Nearly 70% of employees surveyed had their bosses’ personal phone numbers. A quarter had spent social time with them and visited their home, and 60% had met their boss’ significant other. Perhaps most strikingly, almost 30% said their boss had asked them for advice about a personal issue.
Debra Major, a professor of organizational psychology at Old Dominion University who studies relationships in the workplace, says that in general, supervisors and subordinates are more familiar these days than they used to be. “There is definitely greater blurring of the boundaries between personal and professional lives,” she says. “And a lot of it is technology-driven.” In part, the rise of the smartphone — and, in recent years, connectivity apps like Slack — means many employees are accessible to their bosses around the clock, blurring the divisions between life at work and life outside of it.
There’s something else at play, though. Given the social and economic environment in which millennial employees have come of age, it’s not surprising that those workers in…