Should I date my boss?

Dear Edahn,

I am attracted to a guy, and I am pretty sure he likes me too. I have never told him anything, but to make a long story short, he knows I like him. We have been playing cat and mouse games for a long time now, and I really don't want to do it anymore. I am at a point where I'm ready to let things out in the open because these games are starting to play with my emotions, and the things is that I don't even know if there's something there with me and him, if we got together. So, I just want to stop playing games and get things clear, and either forget about him and move on, or ask him out and see where it leads. The thing is, he's my boss. And I haven't started anything with him because of this. It would just be awkward if we had to work together and at the same time be together romantically. 

What do you think about this whole thing? Should I get another job and then ask him out (or lead him to ask me out) or just forget about it all?

So your options are:
   A. Find a new job then confront him.
   B. Confront him then find a new job. ;)
   C. Start leaving uncomfortable notes in his locker/cubbie like "stop playing with my heart you bastard" followed by "we were meant to be together, I know it."
   D. Show up to work after everyone else has left, completely naked except for 3 Post-it notes covering your private no-nos and deliver some ultra-cheesy line like "looks like there's only one thing left on my To Do list, boss."
   E. Stay the motherfuck away.

As much as I'd like to see option C or D, my vote is for E: stay away. Even if you were able to get a new, equally satisfying job, and even if he did have feelings for you, transitioning from job-mode to relationship-mode is tricky.

The presence of an artificial barrier between you -- your professional relationship -- is a double-edged sword. On the one hand, it keeps you physically apart. On the other hand, it brings you together because there's nothing on the line. You're able to get really close because you're not worried about anything bad happening like rejection or betrayal. You also always have a default/backup dynamic you can always resort to if things get uncomfortable. If, for example, things get too intimate and you start to feel uncomfortably vulnerable, you can fall back on your job roles and talk about something else. You're left with a convenient way to get out of any threatening situation. Whether you actually use that to get out of situations isn't that important; the important thing is knowing you have that option. It's like an insurance policy: even if the shit hits the fan, you know you have a way out so you're more relaxed, more available. It's the same reason people get close to "off-limits" married people.

If you can appreciate how your professional relationship has helped you get close, then you can see how abandoning that relationship means you're also abandoning the insurance policy that comes with it, thereby introducing risk and anxiety. You no longer fall back into your professional personas. You're going to have to learn how to get to know each other and relate to each other outside of those roles. There are some exceptionally talented people who might be good at making that transition, but I imagine that most people, myself included, would find it incredibly tricky and uncomfortable. I think of it like being on a blind date, but instead of labeling your discomfort as "routine" and "normal," you think something is "off" and get all tripped up.

So, is it possible to make things work out? Yeah. But is it going to be a smooth transition? I doubt it. And, if you like your job, why risk it by looking for a new job where you might hate your coworkers or hate your work? Best bet is to desexualize your relationship, draw some boundaries around what you're going to talk about, and start seeing some other people. If you elect to disregard my advice (foolish mortal!), find a new job and stalk your prey, then I'd recommend trying to befriend him rather than date him. You can turn the friendship into a relationship down the line if things go well.