One of the “perks” of growing up in Christianity is the clear rules and structure that are provided. Sunday mornings are always reserved for church; prayers at dinners are non-negotiable. You know that a “good” Christian is someone who follows God’s commandments, stays a virgin until marriage, and evangelises on behalf of the church. A “bad” person, on the other hand, is someone who is hedonistic, indulges in their most basic human nature, is selfish, and has turned their back on God. As someone who thrives with structure, this made a lot of mental sense, and when you add on top of all the policing and shaming I encountered as a trans woman, it resulted in me being someone who never strays from the straight and narrow. I appreciated the certainty that religion provides because I knew what I should and should not do. But on the other hand, my process of individuation was delayed, and I developed a deep fear of making “bad choices”.
This mentality persisted when I moved to New York to study at NYU back in 2015. Looking back, it was a period of my life where I felt like I was living the New York dream. I was based in Alphabet City, which is not the most “glamorous part” of New York but felt real, gritty, and close enough to the action on the Lower East Side that I could access the scene if I chose to. I lived close to great delis, pizza parlours, and Mexican joints. $15 USD was all I needed to have a really good time, because I didn’t drink.
I was very slowly coming out of my shell, recording music, going to shows, dressing more boldly, attending my first parties where bowls of drugs were being casually passed around. I never took any drugs crazier than weed, but being around it felt like I was in an episode of Gossip Girl. Not to mention, I was able to fund my medical transition with health insurance at my job, where, for 8-12 hours a week, I worked as a scholarship fundraiser, before joining my friends to hit up Joe’s Pizza or head to West 4th or St. Mark’s for a hang.
But I was lost. I did not know what to do with myself without all the religious policing that was such a huge part of my life. For the first time, no one was judging me for how I wanted to present, and I didn’t have compulsory bible sessions to attend. The freedom was terrifying.
The psychiatrist Irvin Yalom would probably say that what I was going through at the time was my first brush with the four existential fears. Irvin Yalom described that as humans we all have a fear of death, freedom, isolation, and meaninglessness, and any one of them can reduce us to existential dread and angst. For me, I felt paralyzed by the many options I had in front of me with my newfound freedom, and I lived with fear of the bad choices that could “destroy my life.”
Moving off campus helped me combat some of that. One of my flatmates brought much-needed chaos to my very orderly life. She threw parties, invited boys over at the last minute, and dragged me out to join her on the streets for a smoke break. She was fun, charismatic, confident, but also deeply human in her approach to life, which I admired.
Coming from a single-parent household, she was the first in her family to leave her state with a full-ride scholarship from the Bill Gates Foundation. But she also often prioritized fun. She would pull all-nighters before a huge paper was due or wake up late and skip class entirely. There were many days when she’d plop on the couch next to me after missing a big deadline and start ordering delivery and swiping on apps. I was in awe of her carefree attitude, and she inspired many of the lyrics of the song Bad Choices.
I remember that when she went through a tough breakup, she strongly encouraged me to join her hot girl summer era. We had weeks where this became our routine. The morning was when she’d talk about all the guys that matched with her on the apps, the afternoon was when she’d tell me about who she decided to go on a date with, in the early evening she’d pull me to sit on her bed while she did her makeup and got ready while asking for my opinion on how she looked before giving me a recap on the date once she’s back.
While my experience of dating as a trans woman is very different from her dating experience as a cis woman, she showed me what living and taking chances in one of the best cities in the world could look like. I missed out on so much while wanting to be seen as a good and pious rule follower. I remember making all the guys I’m talking to wait at least a month before a FaceTime call to decide if I wanted to go on a date with them. And at the end of my first few dates, I would often stop a guy from hugging me and offer him a friendly handshake instead.
I was very careful with dating in my 20s and only had two long-term relationships. I often chose abstinence and singlehood. It would be a “good year” if I went on 5 dates, and I told myself that I should focus on my career instead because once I reached a certain level of success, I would have more options. I primarily went on park walk dates because I didn’t drink coffee or alcohol, nor was I open to a dinner date where I felt that if they bought me dinner, that meant I was agreeing to sex. I hoped that making these “right” and “good” choices would lead to me meeting the man of my dreams. This was similar to my Christian programming of being rewarded with prosperity for doing the right thing.
But following my attempt, all of that changed.
I lost confidence in myself and my ability to make decisions, let alone do something as vulnerable as dating a man. And so I relied heavily on the people in my life, wanting them to tell me what the “right” answer or action to take was. I wanted to protect myself, and I did not trust myself in doing that.
And so, I externalized my dating decisions to the lesbians in my life. I appreciated that they taught me that looking out for myself is a priority.
I would listen religiously to the Slumflower podcast my lesbian friends sent and read the books suggested. Shera Seven’s “sprinkle sprinkle” became prominent on my For You Page. They all preached the same message.
Prioritize and protect yourself, listen to your own voice, get what you can from men, don't expect reciprocity from them.
This “advice” worked because they were so clear-cut. But in reality, I traded in one Bible for another to take away the anxiety of making decisions. I wanted someone who I perceived as being able to see “life and dating men for what it really is” to tell me exactly what to do.
In this era of dating, I was surprised to find that I could get men to send me money before going on a date, and I loved the validation I got from the lesbians in my life who applauded me for that. I remember feeling quite powerful when a guy younger than me took me on an £800 3-star Michelin restaurant lunch date.
I remember thinking… why did I close myself off to this? Was this available to me the WHOLE TIME? Could I have gone to all the restaurants I wanted in New York, Melbourne, Toronto without using my money? I could’ve invested my money into the stock market or my music career instead of buying myself this expensive dinner that a guy can pay for!!!
It was a bit much though because at points, I packed my schedule so full that I would go on 3-5 dinner dates a week. At the end of it, I was so drained from having the same conversations, but I treated dating as my “fun money.” Whatever I was able to save went into the songs you’re listening to now.
But of course there’s no such thing as a free meal.
The guy that sent me money harassed me for nudes and is constantly trying to re-match me. The guy that took me to a 3 star michelin restaurant turned out to be a super-rich nepo baby that was a Tory with aspirations of owning a privatized army. Needless to say, I didn’t go on more dates with any of them, but it also built resentment from how transactional the whole thing was.
If I were honest, though, at the time, I didn’t care enough about most of these guys to really get to know them. It was an easy way for me to pass time, get out of the house while holding my cynicism and contempt close. Men had simply become the place where I could project a much older grief. Getting money in the face of realizing some men won’t change and only view women as objects for their pleasure may seem radical. But emotionally, it wasn’t that different from wanting to exit life for the anger I felt when I realized that the promise of heaven, God, and justice wasn’t real.
Underneath that anger was grief that was simmering. Grief at the loss of God and grief for how there’s no justice for all the harm I went through. I’ve spent so much of my life trying to be good enough, desirable enough, holy enough, lovable enough, so someone would finally choose me. Dating men transactionally became another way to rehearse that story. It was an easy way to harden my heart by using every disappointing interaction as "proof" that I was never worthy to begin with. When in reality, that’s giving away too much power to someone who never should have that much access and authority over me.
It’s been almost a year now since I’ve dated like that, and looking back, I do think it was good and necessary for me to experience life and dating differently. Without this experience, I would never know that I’m actually not a fan of park walk dates. I would never have found that I enjoy things like going on arcade or minigolf or bowling dates. I also can admit that I do enjoy going on nice dinner dates and working through my restaurant list.
As I heal and continue on my deconstruction journey, I’m building the muscle and ability to discern what kind of structure, routine, and rituals best suit me. I still find myself shying away from the weight of freedom and responsibility that comes with losing God, but I am slowly reclaiming the agency that I once externalized. I’m now at a point where I can see that just as I shouldn’t depend on winning the lottery to become rich, I shouldn’t depend on a man to give me love or entertainment. Life is expansive, and there are many ways to give and receive love. I think that’s healing in action.
My deconstruction journey inspired this 3rd Act in my upcoming debut album (Aug 19!) Before then, I’d love to share with you my new song, Bad Choices.
