What My First Date With A Woman Taught Me About Gendered Dating Stereotypes

As a teenager, I was occasionally attracted to girls, but was drawn to relationships with the opposite sex. While I dated and hooked up with guys, I had a flirtation or two with female friends that extended to a few hot makeout sessions and awkward sexual encounters. I'm definitely not "straight" in the way most people mean it, nor do I identify as bisexual. I place myself staunchly in the "hedonist" or "non-identifying" category when it comes to sexual orientation — but there was always a curiosity stirring in the back of my mind about how things would go if I pursued women more seriously. At 22, reeling from a string of fruitless, lackluster, and abusive relationships with men, I finally took the plunge and went on my first date with a woman.

I had listened to fed-up straight friends dramatically swear off men for years, saying that "switching sides" might be the answer to their dating woes. "It would be so much easier to just go out with girls," they would declare with false confidence. "I'm so over dudes, anyway." Although these comments made sexual attraction seem like a calculated choice and completely diminished the complexity of queer relationships, they piqued my interest nonetheless. I was young and naive and had already hooked up with women, so why not go the next step and see if I would have any success in dating them?

My first opportunity arose when I met Sarah at a bar called Niagara in NYC's East Village. I was newly single after a highly toxic relationship, and in that needy, awkward phase: bored and looking for attention. While I was waiting in line for the bathroom, she walked up and commented on my black leather boots and introduced herself. She said she liked my whole "goth" look and pulled on the hem of my lace mini skirt, grinning. We made small talk for a while, and I admired her impossibly long hair before she shoved me up against the wall and kissed me. (I know this sounds like a faux lesbian erotic novel, but I swear to god I am not exaggerating for effect.) It was really unexpected but welcome, even though she dressed in a preppy kind of way and my dream girl looks like Joan Jett. After a 10-minute drunk make out (which it felt like the entire bar was watching) she asked me what I was doing the following weekend.

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At the time, I frequented a certain goth club in midtown, so I mentioned that my Friday plans were set. She invited herself along, and although I was apprehensive about bringing a "normal" girl out with me, I figured this was my shot to do something I hadn't done before — have a real date with a woman. Maybe a non-hetero palate cleanser was exactly what I needed after my trainwreck of a relationship.

As the day drew near, I was anxious and unsure — the same feelings you have before any first date, really. Would we have sex? How would that go? Would we just end up as friends? What the hell would we talk about? She suggested we meet at The Sidewalk Cafe before hitting the club, which was probably so she didn't have to venture into the cavern of cloves, synth dreads, and ennui alone while wearing jeans and Uggs (sigh, I know). She bought me a beer and asked me some questions about myself. I'm naturally pretty shy around new people, so I chugged the drink and quickly redirected the conversation to her. We had both just finished college and were in between jobs, partying to kill time, delaying the inevitable "growing up." Her interests were in finance, mine in writing and music. She was cute and funny and seemed into me, but because of her gender, I was still curious. Was this a friend-date, even though we had made out before? What did she like about me? Was I just some kind of exotic weirdo or novelty item to her? I felt a little guilty asking myself those same questions though, given that she appealed to me for that very reason. It was like getting one of the popular girls at school to go out with you — like the 16 year-old-miscreant in me was finally being validated in some roundabout way.

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After an hour or so, we left and worked our way uptown to the club. There was a casual vibe between us, but she had leaned over to remove an errant hair from my jacket and I was somehow completely turned on by the gesture. I paid her cover (she was venturing into the devil's lair on my account, after all) and she bought me a drink (designed to look like blood, of course). I led her to the inner sanctum of the dance floor with baited breath and tried to ignore my friends' side-eye surveys of us. Dancing (aka clearing the cobwebs) as seductively as I would with any guy, I lured her into the center of the room. We shouted flirty comments every now and then as the The Bolshoi blared above, before I had to excuse myself to the bathroom.

After waiting an eternity as everyone entered stalls in twos and threes to fix their eyeliner and do coke, I returned to find her dancing with another girl. Let me be more specific: I returned to find her dancing with another girl who looked like me, but was about 10 pounds lighter, three inches taller, and wearing what looked like a latex bikini.

Not wanting to jump to conclusions, I figured they could just be engaging in a friendly grind as opposed to anything overtly sexual. Once I materialized from the fog, Sarah glanced my way but continued to dance with the girl. There wasn't even a minimal effort on her part to pretend she wasn't completely smitten with this newer "better" version of me, and I realized my date had ended as unceremoniously as it began. Embarrassed, I walked away while the two of them continued dancing, crotch to ass. I tried to laugh off the rejection as my older friends shot me pained I-told-you-so looks. They thought my "fake lesbian" turn was immature and forced.

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A week later, I received a text from Sarah to the effect of: "Hey, I had fun with you the other night. I've been thinking about you. Wanna hang?" She was obviously in complete denial of the way she had ended our date, displaying an idiotic (yet convenient) level of selective memory. It was dude-bro levels of face palm inducing, and I was shocked a woman could be so clueless. What happened to girl power and Spice Girls unity and vagina solidarity stuff, I wondered? I texted her back, said I was busy, and left it at that. For the next few months, I occasionally got flirty texts from her late at night asking to hang, until I finally requested she please leave me the hell alone.

This story isn't special, nor is it unique or particularly heartbreaking. In fact, I have other tales of dates with women that turned out far better — but those are for a different article. As anyone who has dated in New York City knows, my tale of bad-first-date woe is standard issue. If I had changed the gender to male, it would sit just right with plenty of straight women — affirming tired tropes of dudes being dogs and always on the lookout for the next best thing. Personally, it was a great reminder for me that men and women never conform to the monolithic stereotypes we have for them — especially when it comes to dating.

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The reason I think it's useful to share this brief but meaningful first foray into the world of dating women is because some hetero ladies are under the false impression that same sex dating is a breeze. Dating a woman is not going to automatically be like dating your best friend — all fun and lingerie lipstick pizza parties (whatever that means anyways). Ask any queer person who dates, and the stories you'll hear are just as messy and heartbreaking and wonderful and satisfying as those who date the opposite sex. Though I had a few more random dates with women over the following year, I learned that I tended to be far more successful occasionally sharing a hot night with a woman than ever dating one.

What my limited experience also taught me was that if you've only gone out with men and feel discouraged by your results, when you fantasize about dating a woman or tell your friends you're "switching sides," you might want to ask yourself what the fantasy is really about. Is it because you're actually attracted to women, or is a part of it because you think it's easier to maneuver the already-difficult dating scene with someone you think you know better because you share some similar body parts?

Bad dates and jerks are inevitable, and no gender or sexual orientation is exempt. However, a little experimentation never killed anyone — however naive, ill-intentioned or misinformed that experimentation was. One bad experience should definitely not deter you from exploring new romantic (or sexual) experiences — I know that for a fact. As the saying goes, if at first you don't succeed — well, you know...

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