Please read the whole post before commenting. I know this is controversial, so context is important. Also, I apologize in advance for my English, I am not a native speaker. This is a burner account.
I (32F) have been friends with Lavinia (fake name), a 34yo trans woman, for more than a decade now. We met 13 years ago through work, before she came out as trans and she started her transition. We were both working at a fast food restaurant, a job I got hired for while I was studying at uni. We became very close pretty soon and stayed friends even after I graduated uni and left the job at the fast food restaurant. After three years into our friendship, Lavinia came out as trans. I was happy for her and I told her I would support her no matter what, since she made the brave decision to finally live her life as her true self. At first, her coming out caused some troubles in her family. Lavinia moved in with my family (also very supportive) for a four months, before she was eventually accepted by her parents. She started her transition and I supported her, mentally, emotionally and also financially. When I moved on from my "uni job", I started to work a job that pays me really really well. In our country, most of the gender affirming therapies and major surgeries are paid by public healthcare, but minor surgeries (such as facial feminization surgery) are not. Since Lavinia was still working at the fast food restaurant, she couldn't afford them, so I offered to pay. In addition to that, I managed to find talented surgeons, as I work in the medical field and I know a lot of doctors. She was really happy and that brought us even closer. I always took care of Lavinia after her surgeries, when she wasn't able to take care of herself.
Recently, though, Lavinia started behaving in a very weird way, to the point I almost cannot recognize her anymore. She started complaining about some health issues she has been suffering from, like PCOS and endometriosis. Initially, I couldn't understand what she was trying to say, so I asked her to explain. She suddenly became defensive and aggressive and told me I was invalidating her feelings and being disrespectful. I wasn't trying to disrespect her, I just couldn't understand how she could suffer from those conditions, since she doesn't have a uterus or ovaries. Anyway, I let it go, as she looked very upset.
Every now and then, Lavinia gets back to the PCOS/endometriosis thing, especially when we are with other friends who ask her how she is doing. She says things like: "oh, I'm doing just fine, but I have been having very painful periods recently, due to my PCOS. It really sucks.". Our friends always look puzzled, because they know she is a trans woman, but nobody ever said anything back to her. Everyone has been walking on eggshells around Lavinia for a while now, to not make her feel uncomfortable, as she gets easily upset.
A couple of days ago, me, Lavinia and a mutual friend (let's call her Jessica, 34F) were having a girls' night. Jessica's husband was out of town so she invited us over to catch up and spend some time together. We had dinner and then they started drinking some wine (I don't drink, because of a health issue I have). We were chatting and gossiping a bit and everything was going great, until Lavinia said something very unhinged. For context: Jessica and her husband have been trying for a baby for about two years now. Unfortunately, she hasn't been able to get pregnant yet. I am truly sorry for her, since Jessica is one of the sweetest and kindest people I know, and I really think she would be the best mother. Her and her husband shared this very personal information with Lavinia and me, because we are all close friends and they trust us. After just two glasses of wine, Lavinia said that she is struggling to get pregnant and started complaining about the fact there is not enough support for "people like her". She said she went to the doctor because of her infertility, but her doctor wouldn't let her get into a program to get IVF. As she was speaking, my heart sunk, because I know how sensitive this issue is for Jessica. I turned my head to look at Jessica and I saw she started tearing up. At some point she got up from the couch and she excused herself to the bathroom. I sat in silence for a minute. I couldn't believe what just happened. When I heard Jessica sobbing from the bathroom, I went to check on her and tried to comfort her. She was devastated. She was very sad because she didn't expect Lavinia to say something like that. I hugged her tightly, wiped her tears and told her I would try to speak to Lavinia, since she really crossed the line this time. We walked together back in the living room, only to see Lavinia taking selfies holding the wine glass, like nothing happened. I made up an excuse and told Lavinia we were leaving. I drove Lavinia home. I drove in silence for the whole ride. Before getting off my car, Lavinia asked why all of a sudden Jessica and I "got a stick up our butt". I couldn't take it anymore and I exploded. I asked how could she be that insensitive and bring up that bullshit of not being able to conceive, as she cannot physically get pregnant. She looked at me like I was the nastiest human being and started screaming that I don't understand the struggle of being a woman. I responded that I did understand what being a woman means, as I am a woman too, but maybe I can't fully understand the struggles of being a trans woman. Lavinia kept screaming, even louder, calling me transphobic and misogynist. I told Lavinia I am not, since I have been by her side from day one of her journey, and I was only calling her out for what she was saying and how she was behaving recently, not for who she is. She said I am disgusting and she is ashamed to have wasted all these years with "someone like me" that doesn't see her as a real woman. This is when, probably, I said something wrong. I said "No, I see you as a trans woman, which is what you are and that is totally okay. I love you, but you have been saying the weirdest stuff recently. It is disrespectful for the women that really have the health issues you are claiming to suffer from. That is not okay. I don't have endometriosis or PCOS, so, as a woman, I respect those who are struggling with those issues. You don't suffer from endometriosis or PCOS and you can't get pregnant, so stop with this nonsense. You are hurting people, your friends specifically." She suddenly got quiet and just got off my car, slamming the door behind her.
I haven't heard from Lavinia since, which is pretty uncommon. We usually text or call each other multiple times a day. I am not sorry for what I've said and I am not planning to apologize. Although, I would feel bad if that marked the end of our relationship. I have honestly considered Lavinia as my best friend for all these years.
So, AITA?