What to Do?

I have a bit of a “problem.” Where I work, and I assume most places are like this, dating the boss is something that is frowned upon. Well, many of the girls I work will are all very pretty, but a little too young for me, out of the +/- 3 years range. They’re 18 to 20, and I’m 24 and I’m not dealing with a girl who has a high school/bubbly mentality anymore. Been down that road. Women alone can be enough drama anyway! The only female co-workers that are my age are managers and maybe one or two other non-managerial co-workers. So…on to the problem. If you couldn’t guess it, I happen to really like one of the managers I work with, and she happens to be the head manager of the entire store. I’ve never been in a situation like this before and am clueless on what to do. I wasn’t really looking for a relationship, but I’m beginning to think, maybe I shouldn’t pass this up. At least that’s the way I think while working with her, that I should take a chance. Though the more I think about it (away from work), I think that I should just leave it alone and don’t do anything!

This has all occurred recently and at the moment I’m trying to read her, which is nearly impossible because I don’t work with her everyday. [Note: reading women period is practically impossible!] She has given me signs that us guys think say to us, “green light” such as her incessant touching. Every time I work with her she just has to touch me, whether it be a playful little punch on the arm when I tease and flirt with her, a gentle touch on the arm or hand to emphasize something, a touch on the chest, or an “innocent” brush against me when she passes by; she just has to get her hands on me! And I don’t mind one bit ! But, and there’s a huge BUT…she’s mentioned that she has been known to be a tease. Guys, you know what I’m talkin’ about. Those women are very, very irritating! I also know that us guys have been notorious for taking women’s signals for more than what they are. So I’ve asked for some friends’ advice on how they see it:

Friend #1 says: “If her situation is good (meaning single status), then I’d say go for it!”
My reaction: That’s what I want to hear, but it’s not really helpful.

Friend #2 says: “Approach it cautiously, she’s got more to lose than you so keep it low key. Try not to go to very public places where you’ll be seen by a lot of people like a popular restaurant. But you’re a pretty low key guy anyway.”
My reaction: Pretty good answer.

Friend #3 says: “I’ve been the boss dating a co-worker and it didn’t work out so well. She’s flashed me at work while my supervisor was there. He saw it and told me to talk to her to stop it. The relationship eventually didn’t work out.”
My reaction: Interesting perspective from the bosses view, but sexes are reversed. I wouldn’t be doing anything like flashing my boss on the job anyway. Not what I wanted to hear but seems more realistic.

Cheesecake61, I know what you would say if you happen to read this: “Pray about it.”
My reaction: No tangible help.

Sigmund Freud version of this conflict for laughs.
Id – Don’t just date the boss, date all those cute young women! So what if some of them are 20 years old, they’re all hotties! Your ego is an idiot and your superego is a moron! Listen to common sense!
Ego – She’s the manager and if she’s caught, she’ll get canned not you. It’s very risky for her. She would have to be willing to take that risk. If she is, remember what friend two said, “keep it low key.” If it doesn’t work out, don’t resort to dating the younger co-workers, you’ve been down that unpleasant road before.
Superego – Seriously? This is an issue for you? From the get go, you were told that you’re not supposed to get involved with managers. Leave it that way and move on!

You know I had to throw in some psychological “thingy” in here somewhere ha .

I’m still on the fence. I feel that the way she is, is just her personality and I could be reading the signs for more than what they really are. I’ve done it before just as every guy has done it before. Though I’ve seen this happen before with where I work, where a boss has dated or “hung out” with a subordinate co-worker. If I hadn’t seen or known about it, I wouldn’t be contemplating this. It shows me that they are a bit lenient if it’s kept on the DL. My general thought at this moment (7 July) is she’s teasing me, I don’t want to get my hopes up too much…but then again, I can’t read women.