Not working on November 9, 1998…

Dear Breakup Girl,

You’ve got the best site on the ‘net and I’ve been sending your address to all my friends. You’re now a “must read” for me and the gang!

Anyway, I’m in my late thirties and have a serious case of the hots for my single, late forties boss. In today’s politically correct world, how can I let him know I’m interested without getting fired for sexual harassment?

I’d appreciate any advice you can give.

— Sassy F&S

Dear Sassy,

Who-hoo! About the “must-read” thing — thanks! — not about the boss.

Listen, Sassy, which is the key word here, “serious,” or “hots?” As far as I’m concerned, it’s not “case,” as in, “of harassment.” Why are people having such a difficult time with this?

To quote myself, if you’re having a cow about the prospect of dating someone you work with — well, you should be. it is, arguably, more complicated and issue-ridden than dating someone you live with. But with all this madness and misunderstanding out there about what is actually, especially post-Paula-Jones dismissal (Who-hoo!), a precise and exacting legal standard, that cow can also be one big red herring that makes us all more nervous around each other than necessary; beneath it all, at work and play, the genders actually do mix way more smoothly than BG’s metaphors.

All of which is to say: sexual harassment and workplace dating are, in BG’s ideal world, unrelated. The only romances you start at work, please, are the ones that appear to be based on real attraction, respect, and promise — which are not a fertile growing medium for harassment.

Which is why I asked you about “serious” vs. “hot.” For your venture to be worth the risk — of alienating co-workers, of derailing the friendship, of being banished to the “bad” copier after a lousy breakup — you have to have a pretty fierce hunch that things could really, truly work out. A hunch that comes from your gut, not from your fourth margarita.

Especially if he’s your superior (or, for that matter, someone you supervise), not your equal. Before you let him know you’re interested — if at all — let your human resources department know you’re interested in the company’s policy, if any, on “fraternization.” Then do a little thinking about company culture — the unwritten policy coded in frowns and nudges and raised eybrows and tacit “Who-hoos!” I’ve heard of firms where office romance — conducted with dignity — is an accepted part of office life; others, a cold Dilbertian/Orwellian hell where you can’t even have a photo of your spouse on your desk. So: Have other people dated, cross-rank, before? Were they feted, shunned, no-big-dealed? Are you on a teeny little team where you’d upset the balance of power? Or would folks be glad and relieved that you two finally defused the obvious tension by doing the deed? You tell me. And leave the report on my desk.

If, after all this, you’re convinced that letting him know is a prudent, adult, necessary choice, do not jump his bones. If you make a move at all, sorry, but it can’t be an unrestrained, passionate, magical thing the way it might be in the real world. It’ll be dicey enough for you to say, prudently and adultly, “Um, I swear it’s totally no problem if you don’t feel the same way, but I was wondering what you thought about taking our relationship to a different level” — and then hear, “No, thanks,” and then have to show up for work the next day. Yikes. See how scary this is?

So consider this, too: as I’ve said before, office love does not have to be all or nothing. There’s a case to be made for chaste workplace flirtation that’s consummated only in a positive, productive, hot energy and serious work ethic. And a little buzz that makes you even more psyched to be there.

Above all, Sassy, remember, key word: “serious.” This whole thing is. As hard as it is to find a guy when you’re in your late 30s, it’s even harder to find a job.

Love,
Breakup Girl