One of my coworkers, when he thinks people aren't doing a good job, calls them ladies or girls. He also doesn't listen to the women on our team, insists on pair programming with them if he has shared assignments with them instead of splitting those assignments into subtasks like he does with the other guys, and is in general a nice dude to the other guys and treats the women like they're junior. If the rest of the men on the dev team behaverd like that, I honestly bet there would be no women on our team. I'm not sure how to approach him about it, but the women we work with don't seem to want to take assignments with him or interact with him, for fairly obvious reasons I guess.
I have handled situations similar to that. I took them aside and pointed out which behaviors were inappropriate and that they risked accusations of sexism if they continued. I didn't have to in my situation but if it were necessary (e.g. they didn't alter their behavior and management wouldn't step in) I wouldn't hesitate to do a little public shaming. For example at assignment time or when you see him insisting on pair programming calling it out right in front of everyone: "You only seem to insist on pair programming with our female colleagues. That behavior appears sexist and reflects badly on the rest of us and you need to stop."
sexism aside, that's textbook un-professional behavior and i wouldn't accept it from a female calling people little boys as a pejorative, either.
tell your manager about it. it's part of the manager's job to deal with stuff like this. if your manager refuses to do anything about it, either tell your coworker yourself or leave.
Trouble is, we are a fifteen person startup and my boss is a friend of that guy's from way back. I honestly would feel odd mentioning it. There's no way to couch it in "what if a hypothetical person..." because he's known this guy for longer than the company has existed.
By passively accepting this situation your are part of the problem. Morality aside, your coworker that denigrates employees by calling them girls is opening your 15 person startup to justifiable lawsuits (discrimination and hostile work environment) that could easily shut it down.
The fact that the main problem source is friends with your boss makes it a more challenging conversation, but in no way alleviates your responsibility of having it.
Sit down and talk with the boss. Sure, he may find it harder to intervene when it's a friend, but he may also have a lot more leverage over a friend than he would over an average employee - namely, the threat of shaming among their shared friends.
The problem I'm having with it is he has to know this guy does this. It's not exactly subtle or I likely would not have noticed. He's been in the room before when it happened, and the two of them go out for drinks on Fridays and such all the time. I think it is not a problem for him or he would have pulled the guy aside and told him.
He may be in denial about other people's perceptions. You talked about bringing it up after you have an escape plan - make sure you're bringing it up with the boss too.
That's my plan actually. Once I have nothing to lose I'm going to tell the guy he's being an asshole to the women engineers and ask if he'd consider not doing that because it's a shitty way to treat anyone. Preferably with boss present.
