There are enough things to be anxious enough on a date; your date's thoughts on your sexuality should not be one of them.

By By Hilary Weaver
Updated: March 27, 2019
Photo: Getty Images / Tom Werner

When I went on my first date with a woman, I was 22. I was interning in New York City for the summer, and on the advice of a mentor, I made an OKCupid account as I began to explore queer life beyond my Midwestern circle.

Having just come out, I wasn't exactly comfortable enough to send the first message, so I did the thing that I now find extremely annoying: I waited for someone to message me. After a few days, someone did, and she didn't waste any time in asking me out. We made a date for a small bar on the Upper West Side-not exactly a queer mecca, though there's no shortage of babies and grandparents-near where I was staying for the summer. (Related: The Best Dating Apps for Health and Fitness Enthusiasts)

I waited in the cramped bar before deciding to take a seat outside and cross my sweaty legs back and forth before she finally showed up. The first thing I noticed were the sleeves of tattoos covering both of her arms. At the time, I was inkless with very thick, dark Zooey Deschanel bangs across my forehead. I pulled nervously on my short black beaded Zara dress as I stood up to greet her, and we made small talk before she looked me up and down and said something that remains one of the only real details I remember about the date: "So, how gay are you-really?" (Related: How "Coming Out" Improved My Health and Happiness)

At the time, I didn't know how to answer the question. I didn't really know what it meant, first of all. Did she want me to pull out the Kinsey Scale and point to a number? Was I supposed to prove to her the number of times I'd watched and rewatched the Allison Janney/Meryl Streep kiss from The Hours? Did she want me to go and shave half of my head right there, put on a pair of Birkenstocks, and rock some flannel? To pull out some kind of qualitative evidence of my queerness seemed absurd, and I was perplexed.

Anxiety for Days

In the few years following, I was nervous any time I went out on a date. Would I be told, time after time, that I wasn't enough? It was never as bad as that first time, but I kept up the comparisons in my head. I wondered if my dates looked "more queer" than I did or if they would decide that my experience and my appearance discounted me. I would leave for a date and have so much anxiety before I got out the door that I couldn't even think about enjoying myself. (Related: It's True: Dating Apps Aren't Great for Your Self-Esteem)

So many of my friends have the same kind of story to tell about a first date or interaction in the queer community. If we dress in femme-presenting clothing, identify as bisexual, or are simply wading into new dating territory, people question our legitimacy in that space.

My friend Dana got married to a woman last year, and her wife was her first girlfriend. When she and her boyfriend broke up at the beginning of 2017, she set her dating apps to only women because she didn't want to date men at the time. She was excited to explore this new part of her sexuality and to meet other queer women. But the dates, as many queer dates tend to do, got really personal pretty fast. Each time, she'd tense up, bracing herself for the questions about her dating history she knew were coming.

"I got really anxious about not being 'queer enough,' she told me. "It was like coming out all over again but in reverse. In fact, in some way, I found it scarier because I didn't want to be rejected by the community I was trying to connect with and be a part of, having been closeted for so long."

No, I'm Not "Just Confused"

I've been out for the entire time I've lived in New York. I have a great community of queer friends, and I get out enough in the local queer scene to recognize the same people over and over again at parties (sometimes, it feels like an even gayer version of Russian Doll). There aren't often moments where I meet someone new who makes me feel uncomfortable about how I present myself or asks how long I've been "out." But there was a while there, when I was 23 and had just split with my first girlfriend, who had several badass arm tattoos, long Haim hair, and could best anyone at L Word Trivia, that I thought maybe there was some truth to this "not gay enough" sentiment, and wondered if I should do more.

I started wearing more beanies and got a few flannel shirts at Uniqlo that I wore in heavy rotation. And as soon as I got a tattoo, I made sure to show it off as much as possible. My friend Emilie recalls doing the same thing after conversations with people who told her she was "just confused" because of the feminine way she dressed or her dating history.

"I realized I was changing myself to try to make myself fit into what people need to see from gay people, and therefore I was far away from who I actually am and how I wanted people to see me," she said.

The moment you start to distance yourself from yourself warrants a bit of a wake-up call. I liked my new button-ups, and I got rid of some of the frilly things in my closet that truly didn't feel like me. But there are moments when I still want to wear the big ball gown to cover the red carpet at the Met Gala, or walk into New York's Cubbyhole Bar after work while wearing a light, airy floral summer dress. And anyone who makes me prove my queer card at the door is not anyone who deserves my time.

I promise that within five minutes of our conversation, I will speak of nothing but my sexual fantasies with Rachel Weisz, and you won't be wondering anyway.

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