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Ask The Band: I Think My Boss Wants To Sleep With Me

I know this is going to sound totally gross and the more I go on the grosser it’s going to sound, but please, hear me out. I’m in trouble here, folks.

I think my boss wants to sleep with me

When I say I think, I mean I’m about 97.5% certain.

He’s not just my boss; he’s also my friend. He’s also 62. He’s also my best friend’s dad. He’s also married. And I could say all sorts of shit, like ‘He’s 62 but he’s a YOUNG 62,’ or ‘He’s married, but his wife’s a drunk and from the outside it sure looks like they have a craptastic marriage,’ but that is making excuses. I’m not doing that.

In the last several months we’ve become good friends. There are times when we’re alone at the office and we hang out and chat. We talk about all sorts of stuff: music, arts, culture, literature, blah blah blah blah blah. He’s interesting and funny and a really good friend.

Years ago I dated a man who was 29 years my senior. I’ve never hidden that. In fact, when I started working at my current place of employment the (old) gentlemen and I were still together. In one of the many conversations the boss and I have had he mentioned that he hadn’t understood that relationship until recently. That I was just delightful to be around or some tune similar to that. I tell you right now just to save you all the time that I most definitely have daddy issues. Being a young lady in her early twenties dating men in their fifties isn’t the norm. I never thought it was gross though. I still don’t.

I’m not entirely sure that I wouldn’t do it. I’m really curious. Not curious enough to ruin a friendship, marriage, my job, etc., but curious enough to let my mind wander. Also can I mention that this is a huge fucking distraction in the workplace?!

That sounds bad, huh? Like I’m a bad person. I’m not, I’m just so fucking confused by the whole thing. But I’m listening to my gut here, and my gut’s telling me that this is what he wants.

I haven’t been 100% honest with you guys. I totally let him take pictures of me. You know the kind. Twice. He’s full on into photography, took hundreds of pictures just like mine years ago, has some bad ass camera equipment, never said anything inappropriate while the sessions were taking place, was super professional and I know everyone says this, but they were tasteful! And the second batch? Well, I think they are the prettiest pictures anyone has ever taken of me.

I know, doing shit like that opens the door to stupid and I just didn’t believe that would happen. All these little things keep adding up and the only conclusion I can come to is that my boss wants to sleep with me. I’m not saying he would or that it will happen, but my instincts are telling me something is there.

Has anyone ever dealt with anything like this? I need help, The Band.