Ask Lynn-A new twist on workplace romance

She’s dating a friend of the boss—but the boss is still in the dark. Could there be a conflict brewing?

By Lynn Harris

ear Lynn,
I have been dating a guy for two months now. He’s 19 years older than me, but we get along, have fun, and understand one another — and his age isn’t the issue, anyway. What is an issue (or could be) is that he’s my boss’s friend.

My boss doesn’t know about us yet. At first it was too soon to say anything because we didn’t know
Can you trust your boyfriend to not overshare about the relationship?
where the relationship was going, but now things are getting serious. I stay the night almost every night, we eat dinner together, and we talk on the phone forever. I want to know if this is going to be a conflict of interest in the workplace.
—Not Safe For Work?

Dear NSFW,
Many employers do have policies covering intra-workplace romance (and Jim and Pam on The Office sure have made it look entertaining), but I doubt any include some sort of Section 5, Paragraph 19 in the HR handbook addressing “When the boss has hot friends.” On the one hand, what you do in your private life, even with someone from his private life, is — technically — none of your boss’s business. But in reality, even with all parties on their best behavior, some public/private overlap is utterly inevitable… and yes, it potentially can affect you.

Let’s try to imagine what some of the relevant issues and questions might be:
  1. If and when you do out yourselves (assuming your boss truly doesn’t know already), will you be uncomfortable wondering exactly what he knows about your after-hours, er, “work ethic”? Can you trust your boyfriend to be as mature as his years might suggest and not overshare about the relationship?
  2. What’s your workplace culture? If your office is one of those places with a foosball table and a juice bar, well, that’s not carte blanche to do whatever you want, but it does suggest some blurring of the lines between work and play, and perhaps a more laissez-love attitude toward office romance.
  3. More to the point, how cool is your boss? Maybe, just maybe, your boss would be the kind of guy who’d say, “Hey, you’re great, he’s great, just keep me out of it.” Or maybe he’s the kind of guy who’d say, if you broke up: “That heartbreaker just kissed her chance to get promoted in this office goodbye, too.” Of course, you can’t know for sure, but this is a matter for serious consideration. As is the question of when — and if — you should tell him in the first place. If you do choose to keep things on the down-low, just remember this rule of thumb: Sooner or later, everyone will know.
  4. Are we talking about your job — or your career? What’s the employment environment like where you live, or in your field? In other words, is this romance worth the risk? The risk that you’ll (at worst) have to leave, or (at best) choose to leave — even if it’s because things are great with Boss Buddy and you decide to quit while you’re ahead. In any regard, that’s a question only you can answer.
That’s the bottom line. I’m not saying it would necessarily be RIGHT for you to lose your job over this, even by choice. I’m just saying that you
Remember this rule of thumb: Sooner or later, everyone will know.
should consider that possibility — or, at least, that things could get uncomfortable for you there — as a reality. If your guy is worth it, given all else that may be at stake, then hey, that’s one of those calculated — even romantic — risks we take in life. If the thought of being jobless, or miserable at work, scares you more than the thought of being without this guy, then that’s your answer. No one can predict the future here, but you can decide what you think feels best for you. And when it comes to that, NSFW, you’re the boss.

Lynn Harris ( is co-creator, with Chris Kalb (, of the award-winning website — you can visit BG's blog to discuss this letter! A longtime journalist, Lynn has written about dating, gender, and culture high and low for Glamour, Marie Claire, The New York Times,,, and many others. She is currently the communications strategist for Breakthrough, a transnational organization that creates pop culture to promote human rights. Submit your own dating questions for Ask Lynn via Your question may be answered in a future column.
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