Ask Lynn-Office Romance Gone Wrong?

A woman in one complicated workplace situation seeks help.

By Lynn Harris

ear Lynn,
I have had a giant crush on a guy at work named Mark since day one. We frequently go out to lunch together and have even seen each other outside of work a few times. There’s definitely a flirty dynamic.

Complication #1: he just got promoted... to being my supervisor.

One recent night I called Mark at home. I could tell that something had been bothering him because he wasn't his usual flirty self at work; I figured it
I could tell that something had been bothering him because he wasn't his usual flirty self at work.
could have to do with his promotion. But while I was explaining that I could tone the flirting down, he asked about the email I’d sent him that said, “Hey Mark, I just can’t keep it to myself any longer that I am attracted to you. I want to be with you. Please don’t say anything at work but respond to this by email if you really want to go out sometime.”

I hadn't sent the email!

I told him truthfully that I didn't write the email and then lied and told him that I wasn't attracted to him—I just enjoyed the flirting. I kicked myself after saying it, but I felt that it needed to be said so work would be normal. As it turned out, my ex-boyfriend Adam had hacked into my email and read some stuff about Mark—and wrote to him. (Complication #2.)

So here I am now, three weeks after the email. Things are back to normal, we’re flirting all the time, and I just like him so much. I am worried about the fact that I told him I didn't like him like that even though I do. Do you think I should talk to him about this? Or have too many bad things already happened, and I should just leave it alone?
-Girl in one crazy situation

Dear Girl,
First, let’s note that you’re NOT writing to ask me about this frankly alarming invasion of privacy on the part of your ex—about which you seem remarkably non-worked up. I’ll assume that you've already read Adam the riot act (or simply ignored his deranged tantrum), changed your passwords (not to mention your locks), and moved on. ‘Cause that’s what there is to do with that. End of story.

Let’s move on to Mark. As I have said in previous columns, there are lots of reasons why people say “I’m not into you” when what they really mean is “I am so into you!” All sorts of crazy-but-human fears, all sorts of crazy-but-human defense mechanisms come into play. In your case, however — while you were put on the spot — your hesitation is not altogether crazy. Why? At least one very good reason: Mark is your boss.

Now, I’m not saying people can’t or shouldn’t meet at work. Given all the time that we overworked Americans spend at the office, geez, where else are we supposed to meet people? Plus, if you work
But a lot, and I mean a lot, depends on your company culture.
together, arguably, you have some similar interests and commitments.

But a lot, and I mean a lot, depends on your company culture. Is it one of those places with a foosball table and a juice bar where lots of people hook up? Or is it one of those places where the last couple who hooked up were asked to leave? Let’s also not overlook the fact that he’s your boss. Never mind that a crappy breakup could get you fired by your ex, which is the mother of all pink slips; you could get into hot water with co-workers if he’s suspected of favoritism. And by the way, don’t be naïve. There are no secrets; if you two date, your office-mates will find out.

So if you want this to be more than flirting — which itself may be risky, especially via email! — you’ve got to think really, really carefully. Ask yourself: Do I really, and I mean really like this guy in a hold-hands-when-we’re-80 kind of way? Or do you just like... flirting? If it’s the former, you still have to consider: Do I trust this guy to have a mature, reasonable, realistic conversation about how you two would handle a romance? And how would you handle a romance, in fact? I’m not saying you are not allowed to investigate the possibility of being with him; I’m saying that these are some of the situations you’d have to figure out before moving ahead. Also, keep in mind that he’s been flirting, but he has not made any serious intentions clear. This is far from a done deal.

If all of this makes you nervous, it should. If all of this makes you feel like maybe you’re better off just flirting, that’s probably good. You’ve already seen just how tricky this workplace romance can be—proceed with caution to make sure it doesn’t get any trickier.

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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