

Oooh! Ursula is a fantastic pick and my personal favorite author. Even if we decide on something that’s a re-read for me from her I’d call it a good problem. And if not, all the better!
What I had in terms of serious movies was “Women Talking”, which is an entire cast of women and a single man who barely speaks. Set in an amish community where the women have been systematically drugged and SA’d. Tragically based off real events, but a fantastic film. Given the subject matter I wouldn’t blame anyone who would pass on it but it is one that prompts a lot of discussion.
You need to tell him not to get defensive.
If he is new to queer spaces and is trying to understand than the first thing is to listen, decanter himself and calm down. If for example he called his friend Jason by the name Tyler, would he instantly say "How could I know? you look like a Jason!* or would he say correct to Tyler and carry on.
I understand hee is trying to be an positive, but before he can get to that step he has to learn how not to be a negative, and being upset that someone isn’t gendered enough to be unclockable is just feeding fire to the most common trans anexity. He’s human, we all make mistakes, he’s not bad, wrong or instantly a bigot for assuming wrong. But he does become those things when he begins to argue.
I’m not trying to be hard on him, honest kudos for the effort, but he needs to work on not lashing out at anyone who made him self-conscious. Just gotta correct yourself and move on. Every single trans person would rather just be correctly gendered the next time instead of making an event out of it.