Dating a Married Man... should I? Could I?

So I know allllll the stigma that goes behind dating a Married man. I don't have a "thing" for married men... just 1! My boss!! We have worked together for about 2 years now. Since then I ended a 12 year relationship and he has been my rock through this whole ordeal. He too has had a rocky relationship with his wife of nearly 30 years. His kids will soon be out of college and he "says" he is leaving her. Aside from our extensive conversations (that I'm sure would be an HR nightmare) we have talked about everything; music, politics, movies, the fact that Kate Beckinsale does NOT like to wear underwear!! Lol my dating life, his wants in a future partner, politics, religion, family and friends... and so much more!! There have been soooooo many movie like moments where one of us just needs the other to do something or say something but neither ever does. Should I? Could I? I've read allllllll the articles on how to tell if he likes me and loves me and alllll signs point to YES!!
Dating a Married Man... should I? Could I?
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