Tits and Ask: Being Bi With…The Boss?

DEAR KEN AND ARIEL: I went to my company’s summer outing, out of town, with lots of partying and drinking. Long story short, I hooked up with my boss. I’m completely freaked out because not only is she my boss, I’m a straight woman with a boyfriend. And she’s married. I’ve never, ever been attracted to women before, and I have no idea what her story is. We just got blasted, ended up going back to her hotel room, fooled around, then passed out. I woke up and snuck out a few hours later. I haven’t seem her yet (she went on vacation after the outing) and I have no idea what to do. Thoughts please!

KEN SAYS: As much as I want to say I feel your pain and hate to see you stress over this, my heterosexual male mind cannot get past the mental roadblock that is two women kissing. And drunk in a hotel room, no less. And one of them older (I’m assuming), perhaps looking to lure a young underling (ie, you) into a web of passion and wrestling and sharing a toothbrush (anally, of course).

On a more serious note, if I had a dime for every time I put my job at risk by massive alcohol consumption, let’s just say I wouldn’t need a job. In fact, my propensity for showing up pantsless in hotel lobbies during sales meetings has launched a hundred weekend retreats for our HR group. My modus operandi has always been to just pretend it didn’t happen. Ass-fucking the new girl from finance during the office Christmas party? Must have been some other pale nerd named Ken. Dipping his cock and balls in the water cooler? No one I know of. Camouflaging myself as the hot female CFO’s office couch? Er, that one’s still in the planning stages.

Anyway, thing is, I’d just drop it like it’s hot. Ignore it. Maybe give it a little, “Cool party, huh? So, I finished the Penske file while you were on vaykay…” and just let it die. It’s likely your boss is every bit as embarrassed as you. If she’s not… well, I’d just watch it whenever she hands you a drink or comes at you with a rag.

Oh, and I wouldn’t keep this thing from your boyfriend. If you love the guy, you gotta let him in on this. Trust me: it’ll be like his birthday and Christmas and free handjob night at the Outback Steakhouse (a real thing) all rolled into one.

Hell, I don’t think you should keep it from me, either. In fact, if you ever find yourself in this situation again, please get some of the action captured on video. It would help me make a more definitive analysis. Unless one of you looks like Bonnie Raitt, that is. Then you can just keep it to yourself.

ARIEL SAYS: Wow, this one’s a doozy. I’d say if this particular “team building” activity was in the annual company newsletter, readership would go up 1000% (as would your stock in trade at various water coolers.)

Sorry darling, I digress. So you got drunk and hooked up with someone at the company outing. You aren’t the first, and certainly won’t be the last. I consider company outing to be akin to “weekend leaves” for soldiers serving overseas–a chance to blow off steam, sample the local wildlife and support the local economy, at least from a horizontal position. Companies know they work you too much and pay you too little, so if all it takes is some cheap booze, loud music, even louder t-shirts and some inappropriate sexual behavior among co-workers to make you suck it up and keep showing up at work, they’re happy to oblige.

However, you somehow picked the boss in your game of beer-goggle bingo. And, according to you, she’s not even your “type.” Well, something is afoot. Here’s the deal: it doesn’t have to mean a thing. Yes, it was your boss. But unless she says something, as far as you’re concerned it was like one of those weird dreams you had involving midgets and a trombone. Better left alone and never, ever spoken of again.

If she does bring it up, or wants to continue, then that’s a whole different kettle of fish. Explain that you were roofied with Ecstasy and you mistook her for one of those giant Furry mascot animals (plushies?). You’re sorry, but you’d like to just forget that the whole thing ever happened (unless, of course, this adds more leverage to your annual review). Exploring your sexuality is one thing; doing it with the woman who signs your paychecks, is, in the words of the immortal Douche-Mayer, “Sexual Napalm.”

Speaking of sexuality, this particular new development might be something to consider further. You might want to discuss it with your boyfriend – I don’t know, he could be fucking THRILLED – but at any rate, a little open and honest communication along with some possible experimentation/third party participation might be just the thing to reignite a little romance in the current relationship and cease your nocturnal investigations of your employer’s bikini wax job.

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