My parents have known my husband for over 25 years. In fact my dad was the one that told me that I should date her when I was 17. They have always tried and eventually succeeded in remembering his name changes (he has had several legal name changes, it sort of makes sense now). They have always adjusted pretty quickly to his clothing style changes as well.
When Jello first came out as male, my parents were completely supportive, but worried that they would have a hard time with pronouns. They would accidentally call him “her” but immediately correct themselves. Unlike what I have seen in other transitioning people, they honestly didn’t mean to miscall the pronoun. This would freak them out and they would apologize profusely and explain they weren’t sure when might get it right since they had known Jello so long as a female.
I noticed yesterday on the phone with them that more often then not they refer to him properly as a male without correction. It made me really proud of them. They still occasionally forget, and then correct themselves, but already this is less and less. There is a learning curve, and the fact that they are going this quickly pleases me, and I think pleases Jello as well.
Just thought I would share that today. I promise there will be more updates, but Jello graduates in two weeks and my work should calm down. After that I should be more talkative.