My best friend took the chat amazingly. If it's framed like it's not a huge scary weird thing it shouldn't be taken that way. However my friend and I have known each other most out lives, had a mutual friend move away to transition in peace (this was before Facebook and it's a sore spot for us always hoping she's ok and happy where she is because we don't know), and both her and I already fall under lgbt* ourselves so we've likely been aware of other genders and sexualities that maybe straight people wouldn't have growing up. The only issue I've had is steering her towards the correct difference between drag queens and trans women. My partner isn't 'fabulous' 'glamorous' in need of a feather boa. He needs cute flat boots in a different size than other women is all. I think she's confused because our friend started out performing in drag before her move and transition so maybe that is what she's stuck on?

My partner sort of mentions things without coming out in his own way (we're using he/him for now). Our first date he asked if trans persons should have access to medical funds and since I thought he was a straight guy I reeducated him. Turns out if I had agreed with him we wouldn't have had a second date, that's pretty clever. He's also told someone dressed as Carmen San Diego that he needed her outfit, and has asked a guy friend to be his bridesmaid. I think he's at the stage where he's figuring out who to tell when he transitions, and everyone thinks these comments are jokes so it's safe for him.

Since there's trans characters in shows your friend might have watched, why don't you suss out their attitude towards all this before bringing it up? It's ok for them to come from a different understanding and upbringing so a little patience can work. However if your friend says unforgivable things or expresses hate towards trans persons please consider the right choice for your relationship. For me personally, my partner and I have many mutual friends and I've made up my mind that anyone who doesn't support him can't possibly be worth keeping around. My bridesmaids are on pause since most are both our friends I'm waiting until he comes out to see who sticks with us. That's me though, I can't say my way of managing things is best. I just feel this way and will remove people from our life to keep him safe and surrounded by accepting people. That's your call how you will act depending on how your friend reacts.