Dear SJ:

My boss at work has been giving me a hard time about a new hire recently. I was assigned to be her mentor and “show her the ropes”. Since I’m a thirty-something married man, I’ve tried to keep my distance from the young, naïve, pretty little girl who could almost be my daughter. But my boss keeps insisting I spend more time with her outside of the office, to “build rapport”. I think it’s dangerous; especially since she has hinted that maybe she doesn’t have the best of morals. One time she let slip that she would “do anything” to get ahead in this company. And she admitted to me that she cheated on some tests and bought essays instead of writing them herself so she could get better grades. Oh, and another thing – my boss is another guy even older than me, and I suspect that he might have hired her simply for her looks. What do I do? Should I approach HR? Call out the boss? Just go with it?

HESITANT HARRY

Dear HESITANT,

I don’t get it. I mean, I really don’t. You’ve got a young, attractive girl practically throwing herself at you, you’ve got your boss’s approval, and you’ve got permission from HR to get close to her. Yet you haven’t yet gone for it. Why not?

You know HR isn’t really bothered by this kind of thing. Why else would they assign you to be her “mentor”? Everyone who’s anyone knows that “mentor” is just code-speak for “hit your quarterly sales and profit goals and you can do whatever the hell you want.” Including banging in the office. Especially banging in the office. Happy employees are productive employees, am I right?

I know it’s on your mind, since your letter concluded with “Just go with it?” I mean, if you were serious about not having sex with this girl, you’d have asked me, “How do I say no? I don’t want to cheat.” But, clearly, that’s not your angle. So we’re working under the following assumptions.

One: she’s DTF. Two: you’re DTF. Three: Your boss is down with you making the beast with two backs. Hell, he’s practically throwing her at you, encouraging you to “build rapport”. You’re going to have to get over whatever performance anxiety or antiquated guilt trip still holding you back in order for this to happen. Unfortunately I can’t be there to smack you upside the head and knock this kind of sense into you. You’re just going to have to man up on your own and decide to do this thing, for your own good, for her good, for your boss’s good, and for your company’s bottom line.

So here’s what you do.

Start with an early “performance review”. This should happen, ideally, on a Thursday afternoon, after most of the work is done for the day. [Why Thursday? Because I want another story to get me excited when I open up my e-mail on Friday.] When she comes in to your office, make sure you’re sitting behind your desk with your pants pulled down. You don’t have to be spanking it or anything, but it would be good if you had a hand in your underwear.

Mention how good she looks. Be specific – don’t just say, “You look nice,” use a direct compliment. “Your blouse really makes your eyes sparkle,” or some other drivel that women love to convince themselves is true and not just an inroad to her panties. Tell her, “Here in the office, things have been going good, but I think they can go better, don’t you think?” And use your eyes to indicate your crotch. Based on her reaction, you can decide whether the banging happens on your desk or in the bathroom at the local dive bar. If she starts touching herself and complimenting you, it’s on like Donkey Kong. If she is a little bit shy, that just means you’ll have to “take the meeting offsite” and call your cousin Jagermeister to wingman for you.

And as this is corporate America, they like to have documentation of everything. Make sure to wear your Google Glass and get some POV videos for your boss. Like you said, chances are good that he hired her for her looks and her willingness to sleep her way to the top. So you’ll need to have adequate evidence for your official written review coming later. Best would be if you save the condom too as evidence of your participation – they’re going to want to match the semen and the vaginal secretions later to make sure she’s not conspiring with a competitor. And when it’s all over? Don’t forget to “cycle back” with regular “action items” about every two weeks.

Best of luck, we’ll look for the resultant bump in your company’s performance to push you guys into the Fortune 500 in the near future.