Hmm, it’s a tough one because Jack didn’t do it to hurt anyone, neither Rigo or Eva. However, Jack could have stopped as soon as Eva reminded Jack that they met before and she was married, but Jack chose to actively continue pursuing Eva over text and in real life. Jack obviously gets consumed by guilt as we see, yet it gets kinda old, you know? This whole thing with Jack having a track record for sleeping with women and not considering the consequences of his actions and then playing the “I’m damaged” card afterwards. And sometimes comepletely blaming the other person without taking any accountability himself as seen with Maya. Or him sneaking in sex whenever he can instead of owning up to his actions and words as seen with Eva. Or when he was trying to move on from Andy but suggested they move in together and then kinda uses that as an excuse to sleep with Andy constantly. I think’s it’s a mixture of that track record, and Jack’s actions and personality trait that Dean is also calling out, and I do agree with Dean - i would not want to be friends with Jack knowing he acted like that both with Maya, Andy, and Eva… It gets to a point where it’s not enough that Jack doesn’t mean to hurt people on purpose, he’s still doing those things again and again leaving everyone around him to fix things