Date a higher-up?

I have a crush on, none other, than my boss's boss. Cliche yes, but there is a context for this crush. A few months ago, I had to make a decision to stay with my current job and break up with my boyfriend, or try to "work things out" in a failing relationship and take a higher-paying job. Talking with my boss's boss, without revealing anything about the decision, made me realize how fortunate I was to have a choice about my relationship direction. Other friends helped me to realize that leaving a failing relationship was a smart move, but my boss's boss is one of the reasons that I stayed with my current job. In the course of talking, I got to know him really well, and found in him someone else who is as much of a geeky workaholic as I am.

Even in some of the worst days of my post-break-up gloom, I was always happy to talk to him, and chatting for a few minutes with him could leave me smiling all day. Lately, it's been really easy to get distracted thinking about this person who I think is brilliant, honest, and kind.

Now, I'm starting to remember what it feels like to be happy. I have a new apartment with a great roommate in a great town outside the city, and I owe some of that to my boss' boss, who is now my crush. Recently, he and I have gone out with a group of people to a local bar, and I'm not sure the crush is mutual, but I can only hold back the shoulder rubbing, giggling touchy-feely for so long when I'm tipsy.

Should I pursue something further? At the least, I want to thank the guy for affecting my life in such a positive way. Any recommendations for how to do that without it being awkward?

Conscientiously Contemplating

Dear Contemplating,

Unless you two have forged a friendship outside of work, I think it's going to be awkward. It's going to be even more awkward because you actually like the guy.

Whether or not you realize it, that choice you had to make about your relationship did not really coincide with your job unless you and your former mate were working in the same cubicle. Perhaps it was coincidence that the two came up at the same time, but the job choice had to be based on what was best for you. You chose a supportive team of people lead by a great guy, and that's a smart match that some people don't make because they were blinded by money.

As a good co-worker and boss's boss, your crush was patient and kind and listened to you. This is what good co-workers do. Perhaps rather than thanking him directly, you could thank him by listening back when he needs it.

As for the crush, making something of it is going to be exceptionally difficult because you do work together and couldn't follow The Golden Rule of Dating in the Workplace. It's really only going to have a chance of working if he isn't somehow your superior and isn't in your department. Neither of you should have control of one another if things go sour.

If you have your heart set on it, I'd at least wait to see if he shows interest before flirting. Make sure you have your head about you if you do end up flirting, so start drinking glasses of water in between drinks. It doesn't pay to make a drunken pass at someone.

Aunt Amy