Crush On My Boss

I'm not sure if this is the right place or not but here is my problem. I have a crush on my boss(Well, more less she's over me. She can't fire me but anyway) I can't stop thinking about her. Shes cute, and shes nice. She always waves I guess that's why I find her attractive because she's not a snob like most women there. The rule at work is can't date someone over you or under you. I heard she broke up with her boyfriend months ago. Because he didn't want to move in with her. I don't even think I have a chance with her. I tend to over analyze certain actions.

I also should add I am shy and I believe she might be intimidated by me. I don't smile a lot. My question is...is it worth flirting with my boss? I mean she seems friendly enough to be my friend. Yet I'm too shy to act like myself. I can't get her out of my mind I tried to believe it wouldn't work out even tried to lose interest.