As with all jokes it matters who the audience is. My friends can make off-colour jokes with me, I can reciprocate with off-jokes. But I would never do this with people not fully aware of my actual opinions. This also counts to clear misogynistic jokes.

My closest female friends they would be fine with it, they’ve known me for years, I’ve supported them in their lowest and they know I would never mean the a horrible thing I say. They’ll happily reciprocate with some toxic male jokes, or some gay jokes. That said, even when I make them they are both clear intended to be jokes, but if they ever looked uncomfortable then it would be my guilt to bear, as at the end, as the audience they are meant to enjoy the joke, not be sad or hurt by it.

Making them to strangers is a big no-no, and if strangers are in the room with you at the time (like a party) you also have to “match the energy” of your friend. That means don’t randomly do something misogynistic that they would understand to be a joke, but strangers would not. I think this is the hardest for most people as they don’t consider that strangers witnessing could also be accidental audiences.

Sounds more like they’re spouting old gay predator stereotypes from the 80s-2000s

I’m a gay cis man and was just on the phone with my best female friend. She was talking to me about an acquaintance that made her feel uncomfortable after she heard him objectifying another woman with a comment about a “slutty outfit” at a Renaissance Faire. She said something to the effect of “and that concerns me because I wear slutty outfits at Ren Faire.” and my response was “Yeah, you’re the queen of slutty outfits!” and then went on to say something actually supportive.

I think every relationship has a certain set of spoken and unspoken rules. I’ve been friends with her for well over a decade. We both poke fun at sex and gender things together and have also had many insightful, non-joking conversations about these things and both know exactly where we stand on them. It was contextually appropriate for me to call her the queen of slutty outfits. Would I say this almost any other woman? Fuck no.

I’ve had friends who are women change in front of me and vice versa to varying degrees of undress but it was always initiated by them and I never barged in or invited the interaction. Gay men engage in sexism, misogyny, etc all the time. We are not immune to it, exempt from it, or capable of being any less harmful. To think otherwise helps no one and maintains existing systems of oppression and power. Men also suffer under misogyny, gay/queer men especially so. We can be powerful allies disrupting sexism in places and situations women typically wouldn’t have access to. That’s what being a real gay best friend is

If it’s OK for the gay best friend to be misogynistic, it’s OK for the woman to be homophobic. Makes just as much sense.

Well, I don’t tell that to everyone immediately and I look and behave like a regular man so nobody would ever guess without at least knowing me for some time. I wouldn’t ever go to female changing room or bathroom expecting it to be fine. It would be just as akward, or even more so when trying to explain that somehow.