This is a spinoff from the Dating Thread and reflects some things that are happening in my life right now:
Has anybody dated anyone that you would consider, on some level, inappropriate, or someone that, because of circumstances, made life very difficult? And not just because you didn't like them...
Examples I can think of: Anybody ever date the boss? Any bosses ever date the staff? Anybody ever date someone significantly older or younger than you? Anybody ever dated someone that was of a different culture that circumstances made tough? Anybody ever dated the same person that a sibling (or parent) dated? Anybody ever date someone with significant bad blood between them and a good friend or family member?
I suppose this could just devolve into Crazy Dating stories... make them entertaining!