That's is very cool Jen, and I would definitely be thrilled!

Knowing that other people are seeing the ~Real~ you, is such an indescribably awesome feeling! I have a story that is a little bit similar....
When I was out only to my mom, my brother and I both went to get our ears pierced; it was my birthday, and he knew I really wanted it done and said he wanted to get his ears pierced too. Anyway, while he was driving us to this local tattoo/piercing place he randomly out of the blue tells me, "You look like a girl..." To which I replied, "Really? Why do you think that?" ...I tried to press him for more info, as I was kinda worried that he had figured it out, but he would only say, "You just do", with a mental, casual shrug. At the time I had been on HRT for a few months and had long wavy hair and boobs by then, though I was just wearing plain boy jeans and a dark hoodie. Whatever my brothers reason, it was the nicest compliment I had ever received; I seriously had to turn my head towards the window and cover my face with my hair as soon as he said those words, as I just could NOT get this ridiculously huge smile off my face for some time.

We didn't end up getting our ears pierced that night (the place was kinda a dive, and they wanted too much money), but I did decide to finally come out to my brother on the way home, emboldened by his earlier words. He did not take it well though, and my feelings were a little hurt at the time, but eventually he started to come around a few months later after we haven't spoken for awhile, asking me questions and stuff about being trans. One year later, he expressed a lot more support after he had studied intersex conditions and gender variance in psych classes, and had made a very good friend or two who just happened to be gay, and/or bi.

I'm super proud of my brother for adopting a nonjudgmental attitude & becoming more open-minded. There's still one thing about him though that hasn't changed; whenever my liking both girls
and boys has come up, he's always like "Don't, trust me, guys are gross! Girls are so much better", which I think is funny for some reason.