Ask Big Daddy

Dear Big Daddy,
I started my first political job a few months ago. I never had a thing for older women before, but I do now. The problem is, it’s my boss. She’s a powerful woman. She’s also married, but I suspect it’s one of those “in name only” things. I’m good-looking, in my 20s. … I think my boss may be interested. My girlfriend is jealous about all the hours I spend in the office and is starting to ask questions I don’t want to answer.    
—Cougarbait  

Dear Tiger Beat,

Two words: oh boy.

There’s so much going on here that I hardly know where to start. You’ve got enough ingredients to start preheating the oven for a career-ending faux pas — which is probably not part of your idealized fantasy.

So let’s get the most important bit out of the way first: You need to start looking for another job. Quietly, and soon. Because what you’ve got going on right now is about as sustainable as the state budget.

On the one hand, it’s exciting. You’ve got one bird in the hand, another looking quite fetching in her tree, and the kind of daily sexual tension that sit-coms thrive on. But the bird in your hand is squawking. If you let this drag out too long you’re liable to end up with no bird, no tree, no job and no girlfriend.

On the other hand, you’ve got no clear way out of your predicament. If you tell your boss how you feel, chances are you’ll either get laid or fired — or possibly both. It’s also hard to know how your boss will feel knowing there’s a jealous girlfriend out there. Women tend to be less, er, pragmatic about these things (read: no little Cougarbait to think with). She could see your girlfriend as an irrelevant nuisance — or as a baby sister to be told all about your cheatin’ heart.

Then there’s the matter of what is really going on with her old man. Your “in name only” may really be “in your lustful, wishful-thinking mind only” (see above). Some couples who seem as frigid as pandas in public are really just using up all their passion for each other away from your prying eyes. And if he’s got your boss for a wife, chances are he might be fairly powerful himself (something you’ll know a lot better than I). If you’re as handsome as you think you are, there’s a good chance he’s noticed you too — as a rival to be crushed under the wreckage of your once-promising career.

Then again, he might be grateful to have you around to entertain the old broad and let him get on with his own intramural activities. When couples have been together for a while, the husband-wife dynamic can take on aspects of other types of relationships: brother-sister, pimp-congressman, zookeeper-rhinoceros. Who knows: Rather than a long ride in the proverbial trunk, the old guy might want to give you a handshake and a stipend.

But you’ll probably never get there beating around the bush. Which is why the job search works so well. Ideally you’ll get a job before she knows, though she may get wind and confront you first. Either way, when the time comes you can truthfully say you’ve developed “feelings” for her that make it hard to work there. You come clean without making a pass.

It also might be a good idea to drop that security blanket you call your girlfriend off at Goodwill first. If you have any real feelings for her, I sure didn’t see ’em in your letter. Does this make long-cheatin’ me a hypocrite? Enough of one to give you good advice. My wife was away in L.A. and resigned to my shenanigans, not here and making noise like your girl.

One last thing: Your office wouldn’t have a holiday party coming up, would it? Because even in the well-oiled world of politics, it’s rare that work and liquor ever mix so freely. Your job is to stay sober and stay late. Who knows, your boss might down a few shots of truth serum, start complaining about her old man and then ask you for a ride home. Sort of like she does right before you wake up.