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“I’m Dating Someone My Boss Dated”

Brittany (not her real name) was feeling good when she walked into work one day several months ago—so much so that her boss, Lisa (also not her real name), asked her why she had a grin plastered on her face. “She said, ‘Oh my God, who is he?'” Brittany told us. “I said his name, and she put her face in her hands while shrieking, ‘Oh my goodness!'”

Lisa had gone on a first date with the guy and never heard back from him, Brittany said. “She asked me if he was still creating an app, as if it was the most unimpressive thing—and she went on to bash him to try to make herself look better.”

Brittany says it just got worse from there. “She started to get really short with me and treated me rudely by giving me extra work, treating me almost as if i was on probation, all for dating someone. It got so bad that I went to HR to report it because I was worried about my job.”

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Eventually, Lisa’s iciness thawed…but more and more women are finding themselves in situations similar to this one, says Jane Greer, Ph.D., a New York City relationship expert and author of What About Me? Stop Selfishness From Ruining Your Relationship.

According to Deloitte’s 2016 Millennial Survey, about 20 percent of millennials are either the head of a department or division or have a position within their senior-management team or board. That, combined with the fact that 22 percent of adults 25-34 have used online dating sites and/or mobile dating apps, according to Pew Research, means you’re more likely than ever to share dates with your supervisors.

“Millennials are of the social media age,” Greer says. “People now talk about all of the intimacies that used to be shared with a partner or a spouse or a roommate. I think there’s something to be said for knowing this is the new norm—but that doesn’t necessarily mean you have to accept it and go along with it.”

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Greer encourages setting boundaries between your personal and professional lives to avoid having to discuss any aspect of your love life with your supervisor. “If your boss is asking you who are you dating, just say, ‘I’m more comfortable keeping my personal life separate from my work life,'” she recommends. “Put boundaries in place to protect yourself from awkward discoveries.”

And while you may be “friends” with your boss on social media, that doesn’t mean you have to talk about anything you’ve posted in the workplace. “You can’t control what she’s going to see, but you can control whether or not you talk about it with her,” Greer says. “Set your boundary. Say something like, ‘Given the nature of our professional relationship, I’m more comfortable not engaging in a conversation about social media.'”

And if you still find yourself in the awkward situation of learning that you and your boss have dated the same person?

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“I would say, ‘This is really awkward and speaks to why it’s really good, going forward, for us to keep our personal and private lives separate,'” Greer says. “I would acknowledge the awkwardness of it and put the boundary in place at that moment.”

At the same time, you should tell the person you’re dating what’s going on. “Say, ‘Listen, you want to hear this small-world coincidence? Would you believe one of the people that you dated happens to be my boss?’ I think being open and honest with the person who you’re dating is important if you’re looking to establish a real relationship and it’s going to turn into anything authentic.”

And who knows—the romantic relationship may end up lasting longer than the professional one, in which case it won’t really matter if things are temporarily strained with your boss.


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