Are you friends with your boss? Would you ever be a friend towards your boss? I am one who has been friendly to my past bosses, as they were friendly to me. But I never really made friends with them on a personal level. I did talk to a few of them a lot, but never really talked to them about life, or spent time with them outside of the work. But, I think if I could, I would be friends with my boss. Would probably make work a lot easier in most cases.