The first two things are really up to you. You follow your heart. There is no black and white here Cas. But if you want some guide lines just think about whether or not the action in question is hurting anyone. Physically, emotionally you think about it. If you come up with more negative answers than positive ones chances are you should act against it.
You should also however keep in mind that humans need to be goofy sometimes. It just isn't an always thing.