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You Asked: Should I Worry About Dating My Boss?

DearSugar --


I work in a pretty small company, with people who are all between the ages of 24 and 40. A few months ago, my boss made a pass at me. I know that mixing business with pleasure is risky, but the thing is, I like him. He's smart, funny, cute and I now see why it's easy to fall for someone that you spend so much time with.

Most of us at work are single, and we'll go out for drinks or dinner together after work. My boss became more and more aggressive about wanting to go out on a date and finally I accepted. We have been together for about six weeks and it's been wonderful . . . until now. People at work have noticed we're dating and are starting to be mean to me. They think that I am dating him for perks and special treatment, but I am not; I genuinely like him and think I am falling in love with him. Should I feel guilty? -- Nervous Nancy

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Dear Nervous Nancy – I don’t think you should feel guilty one bit, but I do think you’d be wise to start updating your resume. I understand you’ve fallen for your boss, and I truly hope it’s a healthy and respectful relationship for you, Miss Nancy. I’m frankly a little bit nervous about the language you’ve used to describe this courtship (the "pass”, “more and more aggressive”), as from your note he sounds a little reckless or dominating. Please make sure you’re treated as peer outside the office, ok?

Rules against workplace romances between colleagues have changed over the years, but most businesses still have policies about bosses and direct reports, and for pretty good reasons. Besides, if there’s any collateral damage, you’ll pretty much feel the brunt of it, as you’re starting to see: the suspicion, negativity or jealousy of your colleagues; professional retaliation should you decide to end the relationship; all manner of heartbreak, awkwardness, and repercussion should he end the relationship.

I want this romance to be good for you, which means I really suggest you keep your eyes open, your head held high, and your business card in circulation.

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