Question:
So I joined this great new company and promptly got a huge crush on the head boss. I really like working there. He helped me out during a life emergency, too. We danced around the whole professionalism thing and hooked up for a minute, kind of while he had a live-in girlfriend. And yet, if I had to ask myself “Would you rather have him come over for a booty call, or should he finish that damn permit submittal?” I’d of course say get the fucking permit.

– Feeling Like a Side Dish

Dear Side,

You already know the answer to this one: DTMFA. Your guy is essentially married to his business, which is actually how it should be. There’s this clip from an old Charlie Chaplin movie where he’s roller-skating on the edge of a balcony, blindfolded, backwards, looks like he’s going to fall any second but somehow he escapes at the last possible moment, over and over.

The image is of a daredevil skating on the edge of the truth, without ever actually falling into the truth itself. Someone who is that close to being honest, but who never quite gets there.

Usually we think of dancing on the cliff’s edge as pushing to the edge of truth, i.e. as long as a person’s still up on that ledge, he’s being technically honest with everyone. After all, he warned you upfront, didn’t he? That makes it OK… right? Underneath it all, however, it’s causing you real emotional pain while he’s off desperately trying to keep his business afloat.

Ask yourself: If the other Board members found out that you two were hooking up, would either of you be able to admit to the situation without your faces turning all red? And if he cares so much about you, why did he vanish into thin air when you asked for simple affection over sex?

That is essentially what is going on here. He’s pretending he has time for you and you’re pretending to be OK with the situation. Even though he declared honorable intentions, his actions are ambiguous. In fact, he’s a bit of a cad. That really hurts. Still, you can’t blame him for your choices – after all, you were there, too.

But don’t run away, either. Stick with the company and keep your mind on the job. He’s still a terrific human being – as a colleague. Also, remember he did take you to the hospital at 4am. That is a real, genuine service. Worth a lot more than a booty call. There’s a lot of good to be had here, so keep yourself busy and stay positive.