Dr. Date

Dear Dr. Date,

What are your thoughts on shacking up with a former boss? He hasn’t been my supervisor for a couple of years now, but it still seems a little weird...

Especially when he calls me his “naughty employee.”

—Not A Naughty Intern

Hey,

There’s nothing wrong with hitting it after you’ve quit it.

But one-way role playing violates company policy. And it sounds like your former boss is into the pretending-like-you-still-work-together thing way more than you are.

Is that true? If you were just a lady your boss met, would he be interested in you? Or is he fetishizing your former professional relationship?

Are you okay with that? I guess all of this comes down to how good the sex is. If the carnal quality outweighs the fact that he’s using you to play out a kooky little fantasy, then step into his (imaginary) office.

—Dr. Date

Dear Dr. Date,

I work security at the U, and I recently met a very fine female guard. We were working our shifts together for a while, and we had a great conversation.

Since that night, I’ve seen her a few times, and I get more interested in her each time we run into each other. I would really like to get to know her better by asking her out on a date, but I’m a little worried. She has been very friendly to me, but she also happens to be pretty friendly to everybody.

I’m not exactly sure if she would feel the same way. And that brings me to the real problem: I don’t want to make my workplace awkward by bringing this idea to her only to get rejected.

Sadly, I don’t work with her consistently enough to get to know her without getting a date with her. So my question is: How do I get this girl without losing my dignity at work, or worse, my job?

—U’s Finest

Gopher Guard,

Another workplace-related question! Is there something in the water coolers? Y’all got me thinking about all the intense office relationships I’ve known, both in real life and in film.

Required watching for any office lovers: “Two Weeks Notice,” “His Girl Friday,” “Secretary,” “Working Girl” and “No Reservations.” Watch those tonight.

Now to the meat of your question.

Well, not yet. First, I want to say kudos for seeming like a really nice guy. I am grateful for your services. You and yours keep me safe late at night when I’m heading over to my bff Goldy’s place. But I don’t like to imagine that you’re chasing tail while you should be hounding criminals and talking on your little walkie-talkie — that scares me. Focus on your job!

Let me pretend for a minute that I didn’t have a vested interest in you paying attention during your shifts. I’ll say this: The work world is changing. I just read on the Huff Po that 84 percent of workers ages 18-29 would say that they would have a romantic relationship with a co-worker. Compare that to only 36 percent of Gen X-ers, folks aged between 30 and 46.

That stat makes sense, since a lot of millenials are choosing work based on their personal interests. The idea that “You are what you do” is stronger today than it was in the past, and it’s stronger in America than it is in other countries.

The best workplace romances are slow builds, a la Jim and Pam. In an ideal world, you’d aim for playing the long game. The longest possible game. So long that by the time you’re about to “win,” one or both of you will have found a different job.

But since you don’t work with her consistently, the long game is not a possibility for you. Sucks to suck.

Speaking of impossibilities, don’t you dare touch her at work. That’s how you’ll lose your dignity and maybe your job, too. In fact, try to keep it as cool as possible at the actual workplace.

But next time you have a shift together, ask her what she’s doing on the weekend. Really ask. Probe.

Girls aren’t stupid — if you grill her enough about her plans for Friday night, or Saturday afternoon, she’ll catch on that you want to spend that time with her. Mention that you might be going to a free film showing on campus or something harmless and lame like that. If she’s interested, she’ll probably find a sly way to take your bait, and eventually, y’all will graduate to getting naughty on the East River Flats, or wherever you randy security guards go.

—Dr. Date