Then you know some lame girls, most girls will make the first move if you're being slow and dickin about asking your friend "would it hurt your feelings if i liked someone, i know im not allowed to like who i like so i figured i'd ask permission since you're my boss, boss"

But it's not even that. You're pretty much saying if your friend was hurt at the end of a relationship you'd play with his feelings even more by going out with the girl who broke his heart.

Mk what if your friend is the kind who goes out with lots of people, sleeps with them, dumps them and then claims he still loves them and they broke his heart. That still sound fair? What if he dumped her and cant move on? Then he shouldnt have dumped her. What if its a relationship where they keep breaking up and getting back together. Is that fair? What if she dumped him and will never get back with him, she hates his guts and he still loves her. You urge him to move on and he cant but she loves you. You try and hold off and your friend says you cant, but you like her too, a lot. You should pass up that chance because hes unable to deal with that its over?

Scenarios 1 and 2 would rarely, if ever happen. If he dumped her I don't see why it would matter. I am talking solely in situations where the friend has genuine reasons to feel hurt. As for the rest. My point is there is no harm in asking... 9/10 times they'll say yes it's fine. It would probably even strengthen your friendship even more by asking. Showing a complete disregard for feelings is not how friendship works. I couldn't care less if a girl is in love with me. If I know that by getting with her my friend will be devastated I would never do it; you know, because I value my friends.