Way back in college, an older friend of mine told me three things that have stuck with me in life.
Never date someone you work with.
Never rent to family or friends.
Never loan money to family or friends unless you don't want it back.
Despite his advice, being a horny know-it-all college geek, I decided to make a move on the new marketing director at our office in SLO. She was bonified crazy but so hot. A year later after we split, it made work so ridiculously awkward for not just us, but our co-workers too, I eventually quit. I should have listened to my friend.