Should I have sex with her?

Should I have sex with her?
We’ve known each other for many years. She always smiles at me, and she’s beautiful with a great figure.
I feel like we’ve gotten closer since last Christmas when we partied together.
During the holidays, she often came over to my place (is that a green flag?).
But from my past experience, I feel like dating someone from work usually doesn’t end well. Plus, with my looks, someone like her probably wouldn’t be interested in someone like me.
Or am I just overthinking everything?