2019-2021: The Ugly Parts

TW: Discussion of attempted suicide and self harm

Today is my 31st birthday, and I find myself reflecting on the past two years. Two years ago, I was in a very bad way. I felt like my mind was being crushed in a vice. I described some of that pressure in Depression, but I left out a lot of details pertaining to issues I wasn't ready to discuss. They were still too raw for me. Looking back on the past two-and-some-change years, I see incredible progress, and I feel ready to address those issues.

On my birthday in 2019, I had a powerful and very certain realization that I was going to kill myself within the next year if I didn't fix my life situation. I saw no way I could continue to live as a man. That same day, I sat down with my parter at the time. (To preserve her privacy, I'll call her "Evelyn".) I told Evelyn that I was going to transition, and that, as per the ultimatum she had given years earlier, I accepted that would mean the end of our relationship. I could tell she was sad, but she tried her best to be supportive. We went out for drinks as friends that night. The next day, we went clothes shopping, and she started figuring out where she would move.1 At the end of the day, I emailed my immediate family and let them know.

I think the email holds up pretty well. I made the grammatical mistake of treating "transgender" like a verb by writing "transgendered", but I think the coming-out email was actually quite good at capturing what was going on in my mind at the time. I've included a slightly modified version of it below. Details about people other than myself have been redacted to preserve their right to privacy.

Hey Family!

I have some big news to share with you all. There's no easy way to say it. I am a trans woman. I have not come to this conclusion lightly. It has been a long, painful journey. In many ways, I've been working on this my whole life, but there was a specific moment when things changed.

One day in fall 2016 something clicked for me. Pieces suddenly started fitting together and I had a shocking realization: I might be transgendered. I started seeing my past through that lens. It just made sense. It was more than just an idea. I felt different, too. I was absolutely terrified. My world was turning upside down. I just wanted to go back to how things were, but no matter what I did I couldn't shake the feeling. It took me months before I told anyone. Evelyn didn't take it well. She was very supportive, but she knew that it would mean the end of our relationship. I wasn't willing to lose the relationship, and so I tried to explain away my feelings in any way I could. Around that same time, life started falling apart. [REDACTED], work got very busy, Evelyn became extremely depressed about losing our relationship, I took over the outstanding debt in the house, and [REDACTED]. It was all too much for me to handle, and I stopped feeling it. I stopped feeling like I was a woman. This was a great relief for me. Things started to return to normal for Evelyn and I, but it was an uneasy peace. I didn't understand how I could have felt the way I did for so long and then loose it. I took it as a sign that I must not really be transgendered.

The next year was extremely difficult. I would occasionally see something that would reawaken my feelings. I would become depressed and worried. Was it starting again? Have I just been ignoring my feelings all along? I would slip into a depression and isolate myself. I didn't feel like I could talk to Evelyn because it would put undue stress on her and the relationship. I didn't want to do that again until I was sure. If I was wrong then I could lose the relationship over a small speed-bump. I didn't want to tell anyone else because I didn't know how they would respond and I didn't want to make a scene with what might just be a phase. I felt alone and afraid. Each time I'd find a way to get back to "normal", but each cycle was harder than the one before it. I didn't understand what was going on. How could my understanding of my own gender change from one day to the next?

On March 31st of this year, I checked Apple's employee news page2. They had an article about International Transgender Day of Visibility that highlighted the journeys of some transgendered employees at Apple. The article broke the dam. I fell apart and started crying immediately. I knew there was no going back. I wasn't ready to call myself "transgendered", but I couldn't deny that I felt intense envy for transgendered people who had worked through their issues and found happiness. I needed to do the same. I started seeing a psychiatrist to work through my feelings.

Since then, I've become increasingly depressed. I eventually accepted that I was transgendered, but I wasn't able to act on it. It was too much. Being transgendered is not an easy life, and I wasn't ready to start living it. Until yesterday, that is. Yesterday I realized that I couldn't bear the thought of having another birthday as "[DEADNAME]". If I couldn't figure out how to live a life I was happy with then I didn't see how I could continue living at all. Once I saw my situation in those terms, my fears about what it means to be a trans woman disappeared. Its life or death for me now, and I don't intend to just give up. I'm swallowing my fear and making things happen. I'm going to be the person I want to be before my next birthday. Today is the first day of my new life. For the first time in a very long time, I feel optimistic about my future. I'm not completely sure where I'm going, but I'm not letting anything hold me back any more.

Evelyn has been extremely supportive throughout this whole process, but it has taken a toll on her and our relationship. The whole process has been extremely painful for her. We broke up yesterday. We decided that it was the right way forward for both of us. There are no hard feelings between us, and I still consider her to be part of my family. Unfortunately, circumstances out of our control have made the relationship untenable.

I'm sending you this because I feel like you deserve to know what is going on, but I am not ready to "come out" to anyone else quite yet. Please do not discuss this with other people. I need more time to stabilize myself before I'm subjected to the questions, stares, and whispered judgements that will inevitably come. If you care about me, please respect my privacy. I know this might be a difficult thing for you to handle, but it is far, far harder for me. Please do not add to my burden.


I didn't know how my family would take it. On some level, it didn't matter to me. I had made up my mind. I was going to transition, and no one was going to get in my way. Still, I was too afraid to press the "send" button. It was just too scary. I configured my email client to send the email a few minutes in the future and then went to pour myself a drink to distract me until the appointed moment arrived. The fact that the email was sent "passively" made it so much easier for me. When I scheduled the email, I knew I could run back to my computer and stop it if I wanted. So, hitting the send button wasn't scary any more. At the same time, keeping myself busy and away from the computer gave me a way to keep my nerves under control while I waited for the appointed time to arrive. At 8pm on the 6th of October 2019, I came out to my family.

Two months later, I found myself in an intense mental breakdown. Things with Evelyn had gone very sour. Our relationship had become incredibly toxic prior to the breakup, and it only got worse afterwards. As I described in Depression, simply keeping myself alive until I started hormones was an intensely difficult experience for me. In Depression, I described a moment where I was struggling with what I described as "my brain rebelling against me". That was actually a somewhat common experience for me during that period of time. I worried that even if I managed to avoid killing myself, the stress of it all would cause my body or brain to break down and cease to function.

By the time 2019 was coming to a close and I was officially starting my medical transition, I was a different person. The year had been a pressure cooker that had catalyzed a change in my personality. I think this is a good time to explore exactly how the year changed me. To do that, I need to venture into a territory I've been carefully avoiding. In Depression, I alluded to how some of the pressure I experienced came from my then-partner, Evelyn. That pressure was a big motivator in the change I experienced.


Before I proceed, I want to be clear that I don't blame Evelyn. I don't think she is a bad person. I think she was trying her best to be good to me, but we were both falling apart at the seams. I really don't want to give the impression that she's the "Evil Ex". At the same time, I do want to describe, honestly, how her actions and the situation we were in affected me. I've been avoiding discussing the role the end of our relationship played in my life because I didn't want to portray her unfairly. Despite the pain I experienced and the impact it had on me, I think she is fundamentally a good person. I wasn't at my best, either. I don't mean to give the impression that I was a perfect angel in this story and that I always acted perfectly rationally. Our relationship was toxic, and that can't be blamed on just one person. In addition, my own internal turmoil and struggle exposed me in a way that made me especially vulnerable. Small blows to my psyche left bigger-than-normal impacts. I can't even hope to objectively describe what happened because I was not in a healthy head-space. My perception was compromised. I can, however, describe my experience as it felt at the time. Its a flawed and unfair description of events, but its the only one I have.

When talking about my struggles with other people, I've largely avoided talking about Evelyn and what happened between us. For example, in my coming out email, I painted a rosy picture by saying that she would always be like family to me. I didn't want to say anything that might make her look bad. I didn't think that would be fair to her. But, by avoiding talking about her, I've closed off a very significant part of my injuries and prevented them from healing properly. I feel that sharing this part of my experience is an important part of helping me put it all behind me.

Evelyn was really struggling in 2019. She was experiencing a great deal of stress at work, her grandmother's health was decaying, and she wasn't handling me being trans very well. I never gave myself space to look after my own needs. I felt like caring for her was always the most important thing I could do. I kept bottling up my own pain so I could help absorb some of hers. When she was hurtful to me, I rationalized it as "this is what she needs right now. I'll be okay. I can take this.". That hurt took a lot of different forms. For example, she started making comments about how she was incredibly angry at me for ruining her life. She talked about how she blamed me and hated me for "lying" to her about my relationship to my gender.

She also started practicing self harm. Her preferred method was to endlessly scratch the back of her hand until it bled and scabbed over. Then she'd pick at and scratch the scabs until she exposed the still-fresh wound. She also started using sharp-ish objects to etch a row of triangles into her leg. I vividly remember coming home from work one day feeling awful due to gender dysphoria. When I walked in the door, she was engaged in self harm and just glared at me in a way that tore me up inside. She hated me, but I just wanted to do everything I could do make her happy.

I tried to suggest that she see a therapist or at least talk to her friends about her experience. She got so angry at me for telling her how to deal with her grief. When I asked her for 5 minutes of her time during business hours to schedule an appointment with a marriage and family therapist, she stubbornly refused. I kept trying day after day, week after week. After over a month of trying to get her to cooperate, I gave up. She later complained about how we hadn't ever seen a couple's therapist.

There were times where she would say things or do things that pushed me beyond my limits. Once, this happened while I was driving. I have never felt so trapped in my life. As I was trying to navigate San Francisco's city streets while sobbing, I seriously considered just stopping the car in the middle of the road and running away as fast and as far as I possibly could. I regret not doing exactly that, but it turned out that wouldn't be my only chance.

Once, she said something hurtful while we were at home and I just ran away. I ended up sobbing uncontrollably on the sidewalk right outside my apartment for hours. A torrent of tears came out as all the bottled-up pain found its way out. I cried about how Evelyn had been treating me. I cried about my dysphoria. I cried about my regrets over waiting so long to accept I was trans and all the happy time I had lost as a result. I felt like my life was destroyed and that I could never be happy again. A homeless person heard me and tried to cheer me up by offering me a piece of candy: a Lifesaver. He said "it might save your life". I didn't want to go home, but I was getting cold and had nowhere else to go.

On the third time when Evelyn drove me to run away from home in tears, I ran up a nearby hill and called my sister and told her everything that had been going on. I told her how I was trans and how my relationship with Evelyn had been breaking me apart piece by piece. Mid-way through the conversation Evelyn found me. I saw her turn the corner about a hundred feet away, see me, and then start walking towards me. I felt dread as she came closer. It felt like my tormenter had hunted me down. I told Evelyn that I told my sister everything about what had been going on. Evelyn seemed a bit embarrassed, and I felt bad for "telling on her". We walked home together.

When I told Evelyn that I couldn't do penetrative sex any more because it made me feel very dysphoric, she sat me down on the bed next to her and then proceeded to angrily cut up our supply of condoms. She put our other sex accessories in a shoebox, wrapped a bunch of duct tape around it, and then stabbed it with a pair of scissors while crying. I watched and kept begging her to be careful not to hurt herself in the process.

Once, she came home black-out drunk after a night with her friends. She was clearly turned on, and pretty aggressively pulled me into bed. Almost immediately she started crying at me about how there was no point in going further because I wouldn't do sex the way she wanted. She quickly passed out on the bed while mumbling about how disappointed she was, and I was alone. Later, I told her we could do penetrative sex again. She asked if it was really okay, and I lied and told her it was. I just wanted her to be happy. I wanted her to stop resenting me.

When Evelyn's grandmother was on the brink of death, she drove home to be there and support her dad during the final hours. She said it was the most difficult week of her life. She asked me to fly to her and drive home with her. I told her that I was afraid to be in a car alone with her. She was very hurt but said she understood. I ended up doing it anyway.


When 2019 ended and I took my first dose of my hormone therapy, I thought "I did it! I made it! My future is bright. 2020 is going to be a good year for me. I'm going to get a healthy social life and finally get to live the life I've wanted for so long.".

In all honesty, 2020 actually wasn't that bad for me. I was terrified that my immunocompromised sibling was going to die during the pandemic, and my feeling of loneliness from losing my entire social life in 2019 sure wasn't helped by everyone retracing into their Covid bubbles. I quickly fled to my home town to live with my siblings and my mother. I knew that living alone through Covid could literally kill me.

Living with my family again was incredibly nice. I hadn't gotten to spend significant amounts of time with my siblings since we'd all grown up, and being able to reconnect (especially with my younger brother) was a special treat. But, I didn't feel like I could work on some of my issues when I was away from my home in San Francisco. At the same time, I hated being in my apartment. I had so many bad memories associated with it that going home to it felt like I was going to prison. By late summer 2020, I had returned to San Francisco. I was optimistic about COVID-19 winding down, and I was ready to start building a new foundation of positive experiences for the next chapter of my life.

I wasn't able to bootstrap a social life, and the loneliness got to me very quickly. By the time my 30th birthday rolled around, I was once again falling apart. I celebrated my 30th birthday with a friend from college, and then went home and came very close to killing myself.

That night, I found myself in my bathroom with a razor and a bottle of rum thinking about how alone I was. It felt like no one understood how much I had struggled in 2019, and no one cared that I still wasn't whole. It seemed like no one cared. I thought about my realization from a year earlier about how I would probably kill myself within a year and I stared at the razor. I even took some time to figure out the logistics of how I could do it. Instead, I managed to get up, grab my skateboard, and get some distance between me and that bathroom. I started taking anti-depressants the very next day.

A few days later, when I asked my older brother for some support he told me he was "sick of hearing the sob story". I called him out on how that was an unacceptable answer. He doubled down and then said I was mentally ill before ending the conversation abruptly.3 I haven't spoken to him since.

By the time winter was coming around and it was clear that Covid wasn't ending any time soon, I knew that I couldn't be living alone, and so once again I fled to live with my siblings and mother.


In early 2021, I once again returned to San Francisco. Vaccines were right around the corner and I had a renewed hope that I could put my life back together. Once I started meeting people though, I realized a new problem I had to overcome.

My experience in 2019 hadn't just driven me into a terrible depression. It had also given me a whole extra gift that had been lying just beneath the surface: trauma. I hadn't noticed it because there weren't many opportunities for experiences that could trigger me, but once I started building relationships with people I found myself having panic attacks. I'd lock up and start crying while memories of 2019 would come back to me. My brain seemed to believe that anyone I got close to would just cause me pain. It was trying to scare me away from becoming close to people. I couldn't get it to stop, and I was worried that I'd never be able to have a normal relationship again. I felt like I was utterly and completely broken. It was completely demoralizing.

Even when I wasn't reliving traumatic moments from 2019, I found myself terrified of upsetting people. I needed them to have only good thoughts about me. I would apologize profusely for the smallest infraction, weird comment, or if I simply wasn't in a perfectly happy mood. My personality and the way I interact with other people has changed. I'm much less assertive in interpersonal interactions. Its as though I'm afraid that the slightest misstep might give them reason to hurt me.

I think that, on some level, I feel like I was responsible for the experience I had in 2019. I practically worshiped the ground that Evelyn walked on. I thought she could do no wrong, and so when she did things that hurt me, I think that on some level I believed that her response was a reasonable one and I had done something to deserve that treatment. I think my extreme sensitivity to the comfort of others is a manifestation of that belief. That's all obviously wrong and I'm trying to correct it.

I'm slowly training my brain to accept that what happened in 2019 was anomalous. Its not something likely to ever happen to me again, and I don't need to be so guarded and afraid. I'm trying to teach my brain that its okay for me to assert my needs and desires. When people are unreasonably hurtful, like my brother was in 2020, I don't put up with it.

I've found some wonderful new friends that have played a large role in my healing process. At the start of the year, I would have a panic attack if I even thought about what it would be like to have a romantic or sexual relationship. A few months ago, simply cuddling with someone could send my mind to dark places. Now I'm off my anti-depressants and I've got a girlfriend!

I've still got a ways to go. In my relationship with my girlfriend, I'm always a little bit on edge and constantly looking for signs of patterns of mistreatment. As my birthday approached this year, I found my mood steadily dropping without any clear reason. I am quite clearly much happier and healthier than it was one or two years ago, but it feels like a dark cloud still hangs over the day. My rough patch only spanned about 2 and a half years, but it still feels like the last time I had a happy birthday was in this distant past.

I don't really know what the next year holds, but I think that I've finally broken through to a happier life. Everything seems to be lining up to make the coming year a happy one. In my 2019 coming out email, I expressed optimism for the future. I think I was right to be optimistic – even if my goal of being happier by the time I turned 30 didn't really work out. There's so much good stuff on the horizon. I'm barely 21 months into my transition and I already feel very satisfied with my results. I pass without any effort4 most of the time, and my gender dysphoria has very nearly vanished completely. I've gotten past my depression, and I'm making progress on healing my trauma. I feel like I'm finally living the life I dreamed of when I started my transition back in 2019, and its so much better than I ever hoped.



Neither of us really felt like our apartment was our home any more. She decided to move in with a friend, and I stayed behind with the intent to move once I had gotten my life in order.


I was (and still am as of writing) employed as an engineer at Apple. I shouldn't need to say it since it should be pretty obvious, but I am not representing my employer here.


I mean, yeah. Obviously. Mentally and physically healthy people don't usually get that close to attempting suicide. Brilliant diagnosis, doctor! That's not quite as sarcastic as you might think. My older brother is actually a medical doctor. I really hope he treats his patients better than he treated me.


See boy mode