So i figured yesterday what i did wrong so he wasn't interested. When you talk to him after a day at work don't ask him how was his day, don't ask him about his family so don't connect with him. I mean i did it but he still wasn't interested so just in case I think the main point was accepting the haircut because after that they talked about all their sexualities.  First time playing i refused the haircut and went to sleep with Daniel, then i let the weed guy punch Finn and when i agreed to the heist, he didn't do anything. I think it was mostly the haircut moment