The Challenges of Modern Dating for Nonbinary and Plural Identities

When Skylar Kaye reentered the dating field, they were not sure what to expect. Coming out of what they describe as a “sexless marriage,” re-entering dating was a new experience that not only revealed a lot about themself, but also a lot about the shortcomings of modern dating in relation to nonbinary individuals.

Kaye is a person of many passions, experiences and identities. At 62, Kaye had spent many years learning about the arts, the world and, of course, about themself.

Their description of themself is as follows: “I am plural. I’m a gender-fluid trans faye. So, I’m nonbinary, gender-fluid. I’m a social justice artist, and so I’m a performer, and I’m a writer, and I’ve directed, I’ve produced a web series, and I’m certainly a world traveler, and at this moment, an expatriate,” Kaye says.

With their experience and constant drive for learning new things about themself and the world, Kaye was surprised to find out that modern dating presented challenges they were not ready for. More specifically, Kaye had figured that the knowledge they had gained from their previous marriage would provide some level of foundation that would help guide their experience.

They soon learned that this was not the case, and that modern dating was a new experience for them altogether. In fact, the experience had been so unique and powerful that Kaye felt motivated to revisit a concept from 20 years prior, writing a memoir. Kaye likens it to the moment in musical theater when the characters suddenly “burst into song,” having no other way to express their emotions.

“When something happens that is so intense, or the emotions are so high, and I can’t take it to fiction or plays or screenwriting, I take it to memoir, personal essay. This is the first memoir that I released, but I wrote one in 2006, and I actually took pieces of that and brought it forward into this,” Kaye says. “I had no idea what the apps were like. My marriage had been, you know, (it) wasn’t a sexual marriage, but it was so loving, and we grew together, and we worked on our relationship … I knew a lot, and it didn’t help me date at all. Like, useless.”

Being older than Gen Z, but more familiar with a Gen Z mindset than those within Gen X or the Boomer Generation, Kaye felt as though they were in a difficult place when it came to modern dating. While Gen Z seemed to understand plural identity and nonbinary identity more than Gen X or Boomers, they were less likely to date someone older than themselves.

“I came into dating, and I knew, I knew that I was in this kind of conundrum of a lot of people when it comes to dating are ageist, right? They don’t want to date somebody older than them, and in Gen X and Boomers, there is so much resistance to nonbinary identities and so much attitude … like, ‘Why can’t we just stick with butch? Nonbinary is butch, right? Trans masc is butch,’” Kaye says.

Throughout their dating experience, Kaye struggled with being mislabeled by the people they were dating. People would assign labels to Kaye that overly simplified their identity, often stripping them of their plurality, or using the wrong pronouns and labels altogether.

“I started dating bisexual and lesbian women, and they struggled with the pronouns, and they tended to want to be able to classify me as either femme if they saw themselves as more butch than me, or masc if they saw themselves as more femme than me,” Kaye says. “Sometimes they would suggest things about how I should wear my hair, or letting the hair on my legs grow, or did I want to start packing? I’m like, this is unbelievably invasive. You’re not asking me what it means to be nonbinary. You’re telling me to be the gender that you’re comfortable with.”

While being mislabeled was one aspect of modern dating Kaye was uncomfortable with, dating as a plural identity posed a different challenge altogether. Though Kaye is open to the world as plural today, they underwent a lot of discomfort sharing their plurality with the people they were dating. It took a lot of vulnerability to allow the people they were dating to see the different identities within their system.

“If I let you meet a 5-year-old, I mean, I’m still there, but I get hurt much more easily, you know. So, that was a real struggle about feeling like I couldn’t be myself … I have a very close friend and my ex, who I switch in front of, and it’s raucous and fun, and both of them would say that me being plural is one of the best things about me,” Kaye says.

While modern dating brought forward various limitations to Kaye as a nonbinary and plural individual, Kaye does not pretend that they have all the answers. Instead, Kaye believes that to be “woke” is to know the limitations that we all have. Kaye writes about their experience as a way to shine a light on the areas that could be worked upon, suggesting that a good starting point is modifying how people approach dating, particularly dating apps.

“I just remember a friend of mine, I was saying, you know, I don’t know that I can call myself woke because I’m so aware of where I’m not woke. And she said, ‘That’s the definition of woke, right there.’ … I think the first thing to address is the problem of the apps. … I really wonder about whether there shouldn’t be dating education about opening your eyes to more possibilities of who you might possibly want,” Kaye says.

In “Bachelorx: A Nonbinary Memoir,” Kaye explores these challenges and what they drew from these experiences. Throughout the memoir, Kaye honors their plural identity through utilizing different fonts that correlate with the speaker in that particular moment. And, while the memoir handles sensitive topics of selfhood and the difficulties of finding love, Kaye’s playful sense of humor still shines through.