but only after a long episode of him misunderstanding and getting it ignorantly wrong at first, being distressed and confused about how out of touch with kids and gender ain't simple like it used to be
right up until some rude asshole does this in his face and he needs to stand up for his friends/ family and suddenly understands the emotional crux of the issue
There's an episode of a 2000's British sitcom "My Family" that has a plot almost exactly like this.
CW: transphobia
Protagonist Ben Harper gets excited after recieving a letter telling that his old friend from uni, Charlie, is back in London and has asked to meet him to discuss something important.
After a few scenes of Ben waxing nostalgic about his old exploits with Charlie, there's a knock on the door and Ben opens it to an unfamiliar woman who introduces herself as Charlie. Ben quickly becomes dismissive of his old friend's womanhood, and complains that she's changed too much and he no longer recognises her. He secretly admits to his wife, Susan, that he's concerned that he never actually knew Charlie that well if she was struggling with her gender identity the whole time they were friends without him noticing.
Eventually, while Ben is in the kitchen he hears his neighbour Roger's mother being transphobic. Hearing remarks similar to what he's said by a woman he despises, Ben quickly realises how big a dick he's been and rushes to Charlie's defence.
To this day, I'm still unsure how the BBC allowed it to be made.
Just look at one the BBC's current sitcoms, "Not Going Out". It's shitty in a fuck tonne of ways but judging by the one mention of transpeople I remember from it is a joke about men cutting their dicks off, it would be way worse if it ever acknowledged queer people in any way beyond occasional snide jabs.