Dear Tell All: I've had a somewhat flirtatious relationship with my boss for the half-year I've worked for him. We're both younger than most of the people in our office, so we naturally have a connection.
Recently we both traveled to a convention, where we texted to set up meetings and stay in touch at the hotel. It started out all business, but our flirtatiousness soon carried over into texting, too. One morning he sent me a selfie of him tying his tie, followed by a few more relatively harmless pictures. He finally crossed the line into sexting with a picture of his shirt unbuttoned. I responded honestly, telling him I thought he looked good. We're both single, and I wouldn't mind taking the relationship to the next level, even though nothing ended up happening at the convention.
This whole thing has overlapped with the Anthony Weiner sexting scandal, and that's given me pause. My instincts tell me it's fine to pursue a relationship at work with a single man I'm attracted to. But Weiner has made the idea of sexting so ugly that I'm wondering if I should trust my instincts in this case.
Dear Available: If you two were equals, no problem, as long as both of you felt the same way. But he's your boss, so there's a power imbalance. What if you got involved and then decided to break up with him? Do you really think you'd be treated fairly in the workplace by your jilted lover? A supervisor should realize he can't put an employee in such a position.
Ideally you would shut down the flirtation and maybe even report your boss to human resources. But let's say it's an absolutely irresistible mutual attraction. You would expect a decent man to talk to you about the sticky situation so you could consider your options. Instead, this guy heedlessly sexted you, consequences be damned.
If you really want to get involved with him, then do it on an even playing field, either by transferring to a different department or getting a different job. Given your boss' sleazy behavior, though, I doubt he's worth the trouble.
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