Problems with dating your boss

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As in, I think about her all of the time and I can’t wait to get to work each day just so I can see her.I think the feelings are mutual, but I can’t be certain because we’ve never spoken directly about it, and we’ve been very professional up to this point.As for leaving your job and then asking her out, that’s a pretty extreme move when you have no signs thus far that she’d say yes … My own manager has four direct reports, all managers.and it puts an awful lot of unfair pressure on her. He has developed a close friendship with one of the managers, Jane, who reports to him. They spend most of each day alone with each other in one or the other’s office.“Other than that,” says Segal lightly, “asking for dates is risk free.” In your training, he suggests, stress that when people are in boss-subordinate positions, even attempting to date is risky—it gives a club to the subordinate that he or she can use down the road.“My recommendation,” Segal says, “is to dissuade.” Some organizations require that managers and supervisors report to management before they start dating, he notes.This has created an environment in which the rest of us don’t trust our boss or our peer because of the relationship.It has fostered suspicion among my peers that our compensation is impacted by this relationship.

Welcome to It’s Complicated, a week of stories on the sometimes frustrating, sometimes confusing, always engrossing subject of modern relationships.

If they are, you can ask her to hang out outside of work sometime.

But that part about reciprocation and paying attention to her cues really matters.

Segal’s remarks came as part of his “Harassment Quiz” at SHRM’s recent Annual Convention and Exposition in New Orleans. Because in the real world, how does a subordinate say no? One good way to talk to managers is to make the point that some things go over the line the first time (for example, “Let’s have sex,” or the use of the “N” word) and some things go over the line the second time (the persistent dating requests).

Segal is a partner in the Philadelphia office of law firm Duane Morris LLP. Not wanting to say what she really feels (“I’d rather hang by pins in my eyes than date you”), she says “I’m busy.” The boss hears, “She’d love to, but she can’t this time.” So he asks again. Now back to the scenario of the supervisor who asked for a date, the subordinate refused, and it appeared that there was no harassment.

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