What are your thoughts on dating in the workplace?

[Rawwwrr!]

I could really use your guys' advice right now.

My boss is very close to the same age as me. We get along very well, we vibe very good, and we are always having back and forth witty, flirty conversations. I usually get her laughing, whether we are talking in person or on the phone. I am definitely hitting "attraction switches" when I talk with her. I can tell there are some sparks there. The only problem is....that she's my boss. How should I handle this? Should I peruse or not?

My plan was to try to get her to hang out with me in a very casual way. Grab some drinks with friends, or hit the town together one night, but not to escalate. Almost try to be just friends at first. I know I would have to take this very slow, so I would have to take baby steps on the escalation. Work on getting her used to hanging out with me outside of work, then take it a bit further.

What do you think is the best way to go about this? Or should I even try it? I don't have a moral issue with it or anything, I am just worried that it will somehow get awkward or she says no or something. It isn't like a random girl in a bar you can just not talk to anymore. I'm not too worried about others at work finding out about it, there is pretty much no way anyone would know about us if we keep our mouth shut.

I don't see her really as my superior at work, I guess I see her more as a friend (except we don't hang out outside of work). I definitely say things to her that I wouldn't say to the rest of the management.

So in short, should I pursue my boss or not?

[Mojo]

I couldn't advise on this one because when I did work as a computer geek at a couple of fortune 500 companies I did not pursue relationships at work because of complications that would arise after a breakup. I didn't want to risk my work environment or even my job. Later, when I started my business, I always kept pleasure and business seperate because it would have intereferred with operations. When an employee tried to seek further relations I acted flattered and politely declined.

But if I had a job that I didn't care much for and don't mind leaving, I'd go for it!

[Bull Run]

Don't shit where you eat. There are millions of women out there that aren't nearly as close to you and your life that you can game. In my experience, you don't date women in your cirlce of friends, you don't date your neighbors, and you don't date your co-workers. It's best that you find women outside of your social circle and that are not a part of your daily life. It makes it easier to cut ties if, and when, the relationship ends.