Death of the author: The gag is that we think Douglas is shockingly progressive when his date tells him she "used to be a man" and he doesn't care and it becomes the most healthy relationship he has in the entire series (and this includes him repeatedly trying to rape Jen and at least assaulting Roy and Moss). But then we remembering he is deviance personified and probably just doesn't care because he has a fun girl he can stick it in. But instead, he misheard her and it becomes the "ha ha, you fucked a dude" joke of the 80s/90s. Which is pretty transphobic on its own and was in the tail end of when that was "acceptable"

Then it somehow becomes a drawn out bare knuckle brawl. Which I don't personally think is transphobic in and of itself, but it is incredibly triggering and plays on the very real fear of trans people getting assaulted if someone finds out they transitioned. So probably not transphobic, but incredibly assholish.

Then, death to the author, we kind of know that Graham Linehan is a complete dipshit who is openly anti-trans and it is hard to give any form of "benefit of the doubt". And apparently Richard Ayoade capes for him constantly. And it is the show that skyrocketed Noel Fielding (the guy we try to forget was best friends with russel brandt and associated with most of his "debauchery" back when it was considered "funny"). So... the show is a mess.

I still think the show as a whole is a masterpiece, but there are definitely some gags that just don't play well. But... I also think it is a perfect example of "just pirate it so that nobody gets any money". Similar to stuff like rurouni kenshin.