Dear Ibby: My boss is super-sexy. I want to make a move but am afraid it could all go to hell—my job and my respect. Is there a way to tell if he likes me or not?
Ooh, naughty. Bosses are probably the sexiest people on the planet, or at least the idea of them is. But chances are, if he’s made it all the way up to boss level, he’s probably really committed to his job, unless he’s just the fortunate son of a wealthy businessman. Most people work really hard and sacrifice so much to get ahead at work that they don’t want to fuck around with the possibility of getting fired by higher-ups or, worse, human resources idiots e.g. Toby from “The Office.” However, that hasn’t stopped people like David Petraeus, head of the CIA or, my personal hero, Bill Clinton from doing dumb, sexy things with the people who work for them. So, if your boss is of the Petraeus/Clinton sort, just wait until they come to you—or on you. If they’re seedy and horny, you won’t have to do much to get what you want. But, if your boss is the stereotypical, self-respecting nice guy all women in romantic comedies end up with, you’re gonna have a problem. A man like this, a “good man,” isn’t dumb enough to fall into that trap, and you’ll look like a total twat for trying to make a move because he will reject the living hell out of you in the name of all things moral and correct. Still, all is not lost. If you take your feelings out of the workplace and into some neutral setting like a bar or wherever you and him feel comfortable, then it becomes less about what’s happening at work that’s wrong and more about what’s happening in real life that feels right. This is what I’d do if I were you. Tell him you’re into him but that you respect his position at work and you don’t want to compromise it or make anything awkward. Let him know you have no interest in fucking up everything he’s worked to achieve. Tell him you just find him irresistible and that he doesn’t have to do anything about it. There. Now it’s off your chest, and you’ve presented yourself in a respectable way. With dignity. And if he doesn’t fall for it, then he’s married or gay or you smell horrible. But at least he knows, and it’s his move, which takes a lot of pressure off your boobs. I mean chest.