About six months in, he, out of nowhere, called me up to tell me that he was questioning his gender identity. This was pretty odd and considerably surprising, given that he never once hinted at being uncomfortable or insecure with his gender or sexuality. I wasn't quite sure how to approach this but didn't want to seem unsupportive, but I still got a weird feeling about this revalation.
When we first talked about it, I pressed him a bit to shed some light on what led him to feel this way. He threw out a few generic answers like "I always felt this way, I dunno" but then he eventually conceded that he felt like he "wasn't physically attractive as a male" and thought he'd be more "physically attractive as a female".
Though I thought this was odd and in hindsight, fairly narcissistic, I felt as though maybe I was being too judgmental and that it was his life and his body, and didn't want to argue with him any further and seem like I was being unsupportive. At the time I hadn't hit peak trans, so I just tried to reassure him that he would always be my friend regardless of whether they were man or woman, but, that they were fine the way they were and to strongly reconsider that maybe other solutions are available to help with their self-esteem and identity as an individual, and to also reckon with the permanence of such a decision and evaluate whether or not it would truly make them happy.
He was content with my response for a bit before he said he was just depressed and didn't know what he wanted, and admitted he was getting ahead of himself, so he would remain male but considered themselves non-binary.
While I chalked it up to a combination of curiosity, maybe some kind of weird identity crisis that would resolve on its own, and likely a little stress for good measure, I realized that my words fell on deaf ears pretty quickly.
He announced to me a few weeks later that he'd be starting HRT and transitioning and the decision was final. Our friends had mixed reactions (some was half-hearted YAAAS KWEEEN shit, some indifferent, but most of us were worried that this was suspiciously drastic and out of the fucking blue) and began asking questions, but started second guessing ourselves when he began pushing back and getting angry that we weren't being more supportive, and that this was "his future" and to not "stand the way".
Fast forward to present day, he lives with his folks still but abandoned his degree plans entirely. We've grown distant and I tried to keep in touch but we no longer have anything in common, and our mutuals don't have the patience to listen to him talk about his struggles as a trans woman. He hasn't scheduled surgery yet but AFAIK is still on HRT and presenting as female but flip flopping on pronouns. I don't know if he's working.
He pissed off one of our friends last year and they stopped talking because he showed up to her bridal shower in what was, apparently, a revealing pink negligee-type slip dress in front of her family and didn't realize it was lingerie (allegedly) and inappropriate to wear as outerwear, and was drinking a shit ton and just overall really embarrassing.
He told a mutual that he "has plans" to move out west and pursue acting and start a weed farm, and I don't know where the actual fuck this came from but it isn't the kid I knew. I'm sure I'll find out down the line that this was all trauma related somewhere but his personality and character changed so rapidly, I am convinced he had a psychotic break or maybe fell victim to brainwashing somewhere. The other day I learned about "twink death" and wondering if he just got anxious about losing his looks with age and it sent him over the edge, but I don't know.