I'm a married 25-year-old woman with a newly opened marriage. I re-entered the workforce a few months ago and found my dream job, but I have to travel a significant amount. My husband and I, with our high libidos, realized it made sense to open up our marriage if I'm away so often. We set down some ground rules and we're ready to try them out.

The trouble begins with my new boss: work is a high-stress environment, and all us co-workers go drinking after work. My boss and I got particularly toasted one night, went back to his place, made dinner together and kissed, but we both passed out before anything happened. Not even groping or petting happened. (Dammit.) I woke up the following morning, made coffee, and left. My boss was visibly too hung-over to drive me, so I said thanks for everything and tucked him in before I walked back to my apartment.

Well, things were a little awkward at work for a while after that evening, but I've been striving to stay professional and friendly every day. My boss has even taken me under his wing for additional training, giving me better assignments with more responsibility, etc. Honestly, Dan, I've wanted to jump his bones ever since my first interview, and it would be amazing to have a friends-with-benefits situation. I think he would be open to the idea, but I don't want to put him at risk with upper management, and I don't know how he'd feel about dating a married lady. I don't even know how to bring up the subject! My husband gave me the green light to pursue my boss, but he has no idea how to proceed either.

My questions:

1. My boss has been treating me a bit more preferentially since that drunken night—is he trying to keep me from talking about it?

2. Is there any safe way (read: avoid getting fired) to ask your boss out on a date?

3. If my boss is interested in me, how do I explain the open marriage policy? That I'm not necessarily looking for another partner—and that my husband and I aren't looking for or a third—but that I just want to have a fun time while away from home, and if he finds a more serious partner, to go for it?

4. How horrible is this whole idea? I get the feeling it's far more likely that I'll lose my job than gain any good relationship, sexual or otherwise.

Help Me, Dan, You're My Only Hope

My answers... after the jump.


1. Maybe the preferential treatment is about keeping you quiet—maybe he's worried you'll file some sort of sexual harassment complaint against him if he gives you a lousy performance review—but it's also possible that your boss wants to fuck you and thinks you're a good worker. It's also possible that your boss thinks preferential treatment is the quickest way into your pants. Remember: he knows you're a married lady, HMDYMOH, but he doesn't know your marriage is open. Since you were drunk that night—since you were fucking shitfaced—it's likely that your boss assumes you regret the "mistake" you made in going home with him and he's showering you with favors and good performance reviews now in the hopes that it'll convince you to make the same mistake again, and to make it sober.

2. You kissed him and spent the night at his place. If he didn't gin up an excuse to fire you in the wake of that drunken night—despite the ensuing awkwardness—I can't imagine that your boss is going to fire you when you tell him you want to fuck him ask him out on a date.

3. Tweak this question so it's a statement and read it or text it to your boss. ("I'm married and I just asked you out on a date. So I should probably explain that my marriage is open. Basically, I'm not looking for another partner—and my husband and I aren't looking for a 'third' or anything—but I want to have a fun time while I'm away from home and I have my husband's blessing. If you should find a more serious partner while I'm here and we're fucking dating, you should go for it. But in the interim...")

4. Is this a horrible idea? Maybe, maybe not. Lots of people fuck around with workmates and get away with it. But if news of your affair were to get around the office—and office affairs have a way of getting around—the preferential treatment you received before the affair officially began could wind up looking mighty suspect to your coworkers. Actionable, even. So you and your boss could both wind up out of job. Just something to consider before you make your move, HMDYMOH.