Tldr: the title

I’ve known “James” for my entire life. Our families are friends. We were classmates in hs and spent almost every day together. At the time, James identified as a woman. I’m very feminine (I like makeup, skincare, fashion, hanging out with my girls) and back then, so was James. We had that in common and it was a big part of why we got along so well.

When we moved for uni, James came out as trans & started hormones asap. I was very surprised, but supported him fully. I did feel like a lost a friend in a way, but kept my feelings to myself. The problem really started after his transition became noticeable.

1. First of all, James became very hostile towards the feminine things he used to enjoy. He says things like “Makeup is for insecure girls”, “skincare is such a scam, only dumb people fall for that”, “olivia rodrigo? are you 12?” & that REALLY bothers me. We’ve had several fights about this. It always ends with him using being trans as an excuse to sh*t on femininity. I understand he has a complicated relationship with it, but I can’t stand how rude and demeaning he is to me, even if unintentionally.

2. Secondly, James & I have always slept in the same bed and cuddled, ever since we were small children. None of the boyfriends we’ve had ever had a problem with that and we’ve never been romantic with each other. Still, after James transitioned, I am no longer comfortable with it. I don’t want to cuddle a male friend, it makes me feel weird. I can’t control my feelings over this. I’d just feel gross. I don’t want to feel like this, but I do.

James has a huge problem with this. When he wanted to sleep over a few weeks ago, I set up the guest bedroom. He was extremely offended and went home. We didn’t talk for 2 weeks, then he texted me again as if nothing happened.

Those 2 weeks were the most peaceful in the past 2 years. We argue every time we see each other. If I don’t make the time to see him, he accusses me of not liking him anymore & abandoning him. The truth is, I DON’T LIKE HIM ANYMORE. I do not like this person. It’s not about the fact he’s trans, it’s about the fact that we have nothing in common anymore and he’s constantly rude to me.

I have tried talking about this with him, several times. He is completely unwilling to consider my point of view & thinks he’s fully justified in being offensive to femininity and that I should get used to it. I don’t want to try anymore. I still love him and don’t want to hurt him. How can I cut him off in the least painful way?

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