A LESBIAN DATING A MAN

When I was seventeen years old, I wrote a novel called The Christmas Child, which had nothing to do with Christmas—or children, for that matter. I was merely setting to paper three conflicts arising in my life: my increasing gender dysphoria, my fear of failing college, and the fact that I was dating a girl and thought I might be a lesbian.

The Christmas Child is told from a third person limited perspective, but follows the lives of three characters of different ages, alternating each chapter. Felix, born Josie, is seventeen and has finally decided to come out as nonbinary and made steps to make their body more neutral and androgynous to cope with their crippling gender dysphoria. Brynn, born Maddox, is nineteen and living the dream of being a theatre starlet in her UC Berkeley theatre major. She has a sweet and supportive boyfriend and friends who accept her as a woman, but when her performance goes wrong in a news exclusive of her being the first trans girl to play a certain character in a musical, her gender dysphoria rapidly worsens and she becomes reclusive and withdraws from public life to the point of dropping out of school. And Callypso is twenty-one and lives with her girlfriend Caoilainn in London, a girl she met four years ago off the internet. Callypso has known she was a lesbian for years, but her estranged Christian parents don’t know that, and her younger sister is only barely beginning to learn.

All three characters are designed off me, although I was probably most like Felix as a seventeen-year-old. However, out of all the fictional characters to be borne out of self-inserts I’ve written into stories in the last couple of years, Callypso best represents me.

When I was eighteen, I began another novel that I didn’t finish called Forbidden Love Affair, and somehow this unfinished novel already boasts over three hundred pages, despite not being close to being done. Shoshanna is an eighteen-year-old college freshman balancing crippling depression and anxiety who is madly in love with her transfem friend Mandy and has z-tier self-esteem. Shoshanna get accepted into a musical, where she spends more time with adults slightly to way older than her, and she grows closer to a thirty-four-year-old man named Angelo. Angelo becomes very interested in her and pursues her until she falls in love with him, and despite the age gap and a host of different incompatibilities, the two decide to date and borderline move in together in the summer.

Callypso represents the version of myself dating my toxic ex-girlfriend when I was seventeen, who was two and a half years younger than me. Shoshanna represents the version of me dating my ex-boyfriend (now my ex-ex-boyfriend), who is sixteen years older than me. And even though Callypso and Shoshanna both represent me, they couldn’t be more different. And despite Callypso being written three years ago, she somehow represents me better than Shoshanna did.

I’ll come up with an explanation for this at the end of this essay.

Callypso is a lesbian dating a girl who represents my ex-girlfriend, who was much younger than me. In the novel, they are the same age. I wrote the story when I was seventeen, but I matured Callypso a lot because I assumed twenty-one was way more mature than seventeen—and I was right! Yet I didn’t let Callypso lose her spark that made me me—she still runs four miles in the morning (which I do now at twenty), and I let her be disgustingly cringe with her girlfriend (which I am, too), but she’s way more emotionally stable and mature and independent. And at least I got that right about my twenty-year-old self! She half-treats her girlfriend like her daughter because her girlfriend Caiolainn is so emotionally immature and self-absorbed and creates drama that makes Callypso feel bad for the sake of Caiolainn remaining the center of the attention.

Shoshanna is a biromantic asexual who doesn’t know how to regulate her emotions. A lot of her internal monologues looks like, He brought up someone else. I want to kill myself. Callypso doesn’t have that, also considering the fact that Callypso is written from a third person perspective and Shoshanna is written from a first-person perspective. Shoshanna is also much newer to college and adulthood and reacts to everything new and different accordingly with a jaw drop and bulging eyes. She, like Callypso, is also wrapped up in her partner. Although, for Callypso, it’s a product of being so loyal and in love with a woman she’s been with when she was seventeen. For Shoshanna, she’s never had a serious in-person relationship before. Now, Shoshanna is dating someone way older than her, while Callypso is dating someone much less mature than her, so Shoshanna takes on a more infantilized role as the man she’s dating half-treats her like a daughter himself. So Shoshanna, being only three years younger than Callypso, seems much younger than her. Granted, there’s a huge difference between being eighteen and being twenty-one, as I have noticed as a twenty-year-old. Because Callypso is more myself than Shoshanna is.

First of all, despite writing Callypso and Shoshanna when I still fancied myself a biromantic asexual, I ended up just being a repressed lesbian. So once again, I have that in greater common with Callypso than with Shoshanna. Second of all, I prefer having a more mature role in both friendships and relationships, taking some control, being the provider, being the older one, etc. I would never in a million years have written down, “I want a much older man to call me ‘young lady’ and treat me like both a daughter and a girlfriend because he’s a childless single adult in his thirties and is killing two birds with one stone with me” as my preference in a future partner, but somehow this man is allowed to get away with it? Again, I’m not totally bisexual because I couldn’t see myself with any other man—I would be very quick to stop any new man in my life from calling me the pet names that this man has, and describing similar fantasies (and I have, in fact, shut these other men down over the last two years). I also couldn’t see myself with a submissive younger man, when I thought I may be able to last year. I attempted to and found that I didn’t enjoy it at all.

And not to bring up drugs, but in the three times I’ve gone on shrooms, two truths became abundantly clear to me. I secretly do want someone older and more experienced than me to take care of me, but I’m also not physically attracted to men at all, and I’m really, really attracted to women and only women to the point where I’m afraid of losing control around them.

Now let me explain why Shoshanna and Callypso are so different, and how I still end up more like Callypso in my twenties than like Shoshanna.

I’ve never had difficulty understanding who I am as a person. Over the course of my teens and adulthood, I’ve discovered new things about myself, like the fact that I’m very explorative and enjoy learning new languages and like pursuing things that get my adrenaline pumping. But I’ve always known that, I tend to connect better with people younger than me. I like teaching people things, I like building people up. I get overly attached to people and I become anxious that people will leave me for someone else they like better; but I’m cognizant of that unhealthy anxiety and have never let it sabotage my relationships.

My relationship with my ex-girlfriend destroyed me. In a sense, I unlearned everything I had always known about myself. I am worthy of love, I’m good at things, I’m smart, I’m a fast learner, I’m talented, I’m productive, I’m never bored, I’m energetic. And then she sucked the life out of me, and I turned into a self-loathing, suicidal, self-harming, lethargic, miserable sack of barely legality, and that’s the person my ex-ex-boyfriend met in 2023, and that’s why it was so easy to become attached to him, even though he isn’t my type by a thousand miles. I was hunting for something that, subconsciously, I’d wanted all my life—an older sister or brother to make me feel safe and feel that I didn’t have to face life alone and experience big milestones for the first time. I suffer from major older sibling syndrome in that I crave being the youngest among a group of people. And from 2022 to 2023, I had that—an online community where I was the youngest and kind of adored fondly by all the members of this discord server. I grew attached to a couple older people during the end of 2022, which didn’t last longer than a month each because they both disappeared. And then I met this older man from another country, and the rest is history.

I think I’ve always wanted to feel like this younger person to be taken care of, but it’s always been a very small part of my identity. It leapt to the forefront of my needs right after my ex-girlfriend destroyed me, because I was in a coping mode, and my brain was trying to survive a tumult of emotion and illness. So Callypso is more myself than Shoshanna is, because she represents the me slowly being eroded by my ex-girlfriend—the me that I have reconnected with over the course of 2024—and Shoshanna represents that brief period of my life where I was looking for someone older and stronger to take care of me. And in a sense, Shoshanna still exists as this insecure eighteen-year-old child that my twenty-year-old superego is trying to parent and protect like a father.