Miss Information

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Miss Information is off this week. She’ll return next week with an all-new column.
Until then, enjoy this special "Best of Workplace Hook-ups & Fuck-ups" Labor Day edition.


Dear Miss Information,
My boss recently hired a girl to work for the holidays. If my gaydar is correct, this girl is a lesbian, and a very attractive one at that. Normally, I wouldn’t waste any time getting to know her, but I work in a small, conservative environment. I really wouldn’t be able to say anything alone without someone overhearing. How can I drop hints that we play for the same team without ruffling any Republican feathers? — Sapphic Secret


Dear Sapphic Secret,
Two years ago I thought I was being all She-Wolf by escorting my drunk-ass office crush home from the holiday party. I knew nothing about his relationship status because I was too discreet (a.k.a. chickenshit) to ask, but I figured he’d fall in love with me somewhere on the cab ride back to Brooklyn. Not only did I not get any, I spent the next morning scrubbing his stomach contents off my living-room floor. Later that day, I discovered that he had a serious girlfriend. Lesson learned: Do your research.
How will you do that, Sapphic Secret? By being ultra-observant of the clothes she wears, the food she brings in for lunch, her cubicle décor and the book that’s sticking out of her purse. You’re essentially looking for anything you two have in common that will provide an excuse for an out-of-office interaction.
If it’s the kind of office where it’d be weird to do such a thing, try dropping a few gay pop-culture or literary references and see how she responds. It’s not as direct as the first tactic (most of my gay friends can’t stand the Indigo Girls, and I know an equal number of straights who love the Pet Shop Boys), but it may help you ferret out some useful information.
All that aside, if she’s only employed for the holidays, why not wait until after she leaves to ask her out? It’s much less dicey professionally, and your request for her phone number could be played off as networking, not girl scouting.


Dear Miss Information,
I just got a part-time job, which is great, because I’m broke. My boss is extraordinarily hot, and I’m dying to fuck him, but I’m worried it’ll mess things up. I haven’t had sex in weeks (a self-imposed dry spell; I’m trying to be less needy) and I’m getting desperate. Is there any way to make it work? — Lusty Admin. Assistant

Dear Lusty Admin. Assistant,
Fucking someone at the workplace is not the wisest idea. Fucking someone with the power to fire you only ups the idiocy ante.
Lots of people choose to ignore this wisdom. Some go on to forge long-lasting relationships from what started as a quick hump in the supply closet. Others wind up with their hearts flayed open and a boot print on their ass, collecting unemployment.
In short, it’s a gamble, and you have to decide whether it’s worth it. In your case, I don’t think it is. You’re dependent on this gig financially and can ill afford an unexpected consequence like getting fired. You’re also trying to be "less needy" with men, and getting enmeshed in an uneven power dynamic will undermine that goal. Take a step outside yourself and look at where this is going. I think you’ll see some of your same old patterns recurring.
If you’re really that horny, find another guy to scratch the itch. And if this is all going in one ear and out the other, at least wait until you’ve banked a few months’ rent before you hop into bed with your superior.

Dear Miss Information,

It’s an old story: I’ve fallen for a coworker. Over the past few months we’ve engaged in a couple of after-work make-out sessions, but she insists there can be nothing more because we work together. I’d accept this, but I just can’t seem to — I really do think I’m in love. My question: is it possible to respectfully pursue her? Or is any pursuit a sign that I don’t really respect her and that I’m just a selfish prick? (Oh, and if you could offer any tips on how I might pursue her, that’d be great.) — Besotted in Berkeley

Dear Besotted,
If you put funny Post-Its in her cubicle and deliver her favorite candy bar via inter-office mail, then no, you’re not a prick. If you barrage her with emails, visits to her cube and subtle threats about telling the boss if she won’t join you for an evening of French cinema, you’re still not a prick. You’re a white-collar stalker.

Office romances make people paranoid, and this paranoia causes them to apply a higher standard to prospective partners. There’s "Hot," and then there’s "Hot, but do I really want to take the risk?" Ninety-nine percent of folks are probably going to fall into the latter category. Including you. We also don’t know if she’s using the coworker thing as an excuse because she’s not that into you, or if it’s a genuine showstopper. For all intents and purposes, we’re dealing with a long shot. Forgive me if this sounds calculated and grody, but you need to court this woman like you would a client. Conduct yourself with patience and class and go for the long, slow sell. Easy on the gold jewelry and aftershave, Besotted. When you go out for a drink after work (i.e., schmoozing with the client), see if you can get her to reveal the reasons why she wouldn’t be into dating a guy from work. It’s too obvious if you ask her outright, but more general questions, like, "Who was your first workplace crush? Mine was the girl at the pizza shop, blah blah…" and "What was your best/worst breakup?" will open the doors to her fears and reservations.

Then you use that information to inform your behavior (listen to me, all businessy and shit). If she’s freaked by guys who are clingy, take your time returning those emails and calls. If she had an ex screw her over by spreading rumors, show her how good you are at keeping secrets, even if it’s something stupid like stealing pens, or spilling by the coffee machine and not cleaning it up.

Barring that, the best thing you can do is just lie low, be the best possible version of yourself and continue to explore other romance options. This is a long shot, and your dick deserves a better shot than one ticket in a lotto.


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