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The Globe and Mail

It may be cool, but is it okay to hang out with your boss?

The Jungle is a column that uses connections through social media to explore the fault lines in adult relationships.

In-jokes in professional e-mails, secretly signaled mid-day coffee-escapes, and plans – covert or otherwise – after office hours, sound like the standard plays of work romances, especially the ethically awkward relationships between employers and their employees. But, they might just be friends.

As workplace mores change in tandem with cultural standards, supervisors and the supervised are more likely to want to hang out, albeit within complicated and shifting contexts. Thanks to a freelance and gig-based work culture, a tighter economy and the noncommittal inclinations of twenty- and thirty-somethings, more people move more quickly between jobs, companies, industries and cities, all of which diminishes the formality of traditional colleague-relationships.

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Add in the tether of smartphones, social networking, longer work days and more fluid schedules, and "work" and "home" have been fundamentally recast. They're no longer oppositional spaces.

All of that quasi-intimacy can make the workday, and even productivity, better.

Matt made friends with the staffers who worked for him on a political campaign, and he admits that partying with them was high-risk boss-behaviour. "What if I had to fire or discipline [someone]? What then, would they just bring up the time that I lost the keys to the rental van once or puked in their sink?" He says that because he wasn't hard on them, "they ended up working pretty hard."

Without the boomer-esque work constants of eight-hour days, 30-plus years leading to a pension, and without attendant old-school camaraderie and belonging, unofficial benefits like a nice, chill boss, count.

Still, power differentials can be awkward to overcome; it sucks to have to discipline the same person you're hanging out with later. Matt never had to fire his work-buds, but @jaygootz, a.k.a. Jené, tweeted me that she is "still friends with the office manager who fired me almost a year ago." She explained via e-mail that "The day we got back from Thanksgiving break, she walked into my office, white as a ghost, and told me that I was being let go … I think she was more upset than I was." (They're cool.)

"Freditor" is my word for it, when I'm friends with one of my editor bosses. Acknowledging both aspects of the relationship is the only way to understand what they can, together, offer.

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