My First Date With A Woman Was Nothing Like What I Expected & I'll Never Forget It

I can’t remember my first kiss. I can’t remember if I lost my virginity to a girl or a boy first. I’m not even sure who my first real crush was – I had a lot at once. But one milestone that I remember viscerally was my first date with a woman.

I had been having sex with Charlie for months. We were score-keepers together for the girls’ basketball team — Charlie because she loved sports, me because I just wanted to be close to Charlie. We’d take a school bus filled with sporty girls (purr) to whichever high school the game was at. Charlie would watch my breasts bounce as the bus went over Long Island highway potholes and I’d write cheesy poems about her for my creative writing elective. Then we’d take the bus home and go secretly watch The L Word in her basement, complete with Baked BBQ Chips and mini Kit Kats.

I don’t remember our first time being ceremonious — queer sex can be hard to define. I remember the first time she slipped her hand into my panties when we were sitting in front of my family's computer. I was sitting on one of those ridiculously huge chairs shaped like a giant hand. Remember those? I kept all my clothes on. And focused on my breathing while she lightly ran her fingers on me. I was so blissed out I didn’t even have time to panic. But that wasn’t sex.

I remember sitting on her lap while we hung with friends. Just being close to her was enough to make me wet. I was so wet that I soaked through onto her jeans and I had to pretend that I got my period and act embarrassed. That wasn’t sex either. And it certainly wasn’t a date. I grew up on rom-coms—I was DYING to go on a real old fashioned date but I didn’t dare mention it. I was scared to be out in public with her.


“I want to take you out. For real,” Charlie said to me sleepily one night as we lay in her twin bed, under her amateur artwork she’d made in school. I was flabbergasted. I thought our whole relationship would live and die in the fluorescent lighting of her basement and the public restrooms we snuck into during basketball games.

But once she mentioned it, I let myself fantasize about all the cute rituals we’d participate in. I wanted all the things the straight couples had: anniversaries, presents, and maybe even a promposal. It’s the 21st century, after all, I wanted the right to be as corny and basic as all the heteros in our school, damn it. But the thing I wanted the most was to go see Dear John in theaters. You know, that super cheesy movie with Amanda Seyfriend and Channing Tatum. In the commercials, he'd say, "I miss you so much, it hurts." I thought it sounded like the most romantic thing ever. Charlie said she’d take me that Friday.

I got the most orange spray tan Long Island could provide, winged my eyeliner almost to my ears, and wore a royal blue Hollister top with Hollister jeans. I thought I was the coolest b*tch this town had ever seen. Then we got to the movies and it was completely sold out. Womp.

We went home and watched The L Word instead. Charlie promised to take me out again the following Friday. That week, I found out I didn’t make our high school show choir. It had been my life’s mission to get in. Charlie said the date would console me, but I was embarrassingly over-the-top devastated. My dad has a hilarious home video of me threatening to kill myself all because I wouldn’t get to sing "All That Jazz" in a hand-me-down costume in a stuffy auditorium to Long Island moms sipping Pinot Grigio out of water bottles.

But eventually, it was time for our date. I was super bloated from emotionally eating all week, and my Hollister jeans wouldn't button. I was off to a rocky start. Charlie’s mom dropped us off at a pizzeria with a restaurant in the back (Long Island is basically made up entirely of pizza-restaurants and nail salons.) I welled up with tears at the thought of eating pasta. I already felt so bad about myself. But Charlie was so excited, I tried to put on a brave face. She looked so dapper and adorable, in her American Eagle polo, jeans, and men's loafers. She even slicked her newly short hair back.

I became painfully aware that we didn’t belong on a date at the restaurant. I fixated on how young we were, on how queer we were, on how disabled I was, on how fat and ugly I felt. I convinced myself that everyone was staring at us. “The waiter hates us,” I said to her. I thought we were a walking freak show. Our illusion as a couple had shattered and we were just some weird troubled teens that wanted fettuccine alfredo. It didn’t feel like a date. I couldn’t feel anything besides how uncomfortable I was.

Her mom didn’t answer the phone once we finished. My parents couldn’t get us for an hour.

“I know! Let’s split a milkshake,” Charlie sweetly suggested. I was over the whole thing, but Uber hadn’t been invented yet. By the time we walked into the ice cream shop, my tail was practically in between my legs just wanted to curl up and die. I didn’t think it could get any worse. That’s when the front door swung open

“GIVE MY REGARDS TO BROOOOAAADDWAYYYYY…” a gaggle of black and gold glitter piled in to the ice cream shop. The show choir that I had been rejected from had just finished a show. The next thing I knew, we were surrounded by a sea of jazz hands. While they shouted orders for scoops and sprinkles, I did my best to disappear. But it’s not so easy to disappear when you’re a teen lesbian couple, and one of you has one hand.

“Hey Dayna!!!!” Carina, an impossibly beautiful and chipper soprano sang at me. The rest of the group eyed us up and down. A pair exchanged sneers while staring at Charlie’s masculine countenance. “Dykes,” one of them whispered. That’s when I sprinted outside.

Once Charlie caught up to me, she was in tears. “I thought you wanted a cute date,” she started. “I DO, BUT NOT LIKE THIS,” I screamed. “I just want to be older, and pretty, and covered in tattoos living in a lesbian-populated city.” I wailed. I exploded into tears.

Charlie held me while I sobbed and sobbed. “I just really wish I had made the show choir,” I whispered over and over. But she knew what I was really upset about. Her mom eventually picked us up, and Charlie held my hand the whole car ride home.

“Dayna’s gonna be on Broadway someday, isn’t she mom?” she said, giving my hand a tight squeeze.

That night, we had sex. All of our sex, like I said, blurred together. But this time stood out because I remember really feeling her, feeling our bodies together. I used to have sex with my bra on because I was so self-conscious, but this time, when she went to undress me, I didn’t hesitate. Even though I couldn’t button my Hollister jeans and I was full of carbs and ice cream, nothing could get in the way of my desire for her. Our bodies fell into each other, We were hiding in one another, and finding one another in each other. Nakedness finally didn’t feel uncomfortable. It felt like, excuse me for saying something so vile, making love.

So our first date wasn’t a total success or a horrific disaster. I’ve since gone on countless dates and I will never forget that one. But to this day I refuse to go on ice cream dates for fear of getting hate-crimed by a high school show choir.