I can recall a whole slew of shitty types of women I slept with in my 20s.
With certain types, a recognizable pattern emerged. When I was in my early 20s I had an alarming sort of disorder that made me compelled to sleep with mean women who wholly disapproved of my existence. My shrink says it’s because at the time I had such a low opinion of myself that I subconsciously sought out sex partners who had an equally low opinion of me, in the hope that if I could convince them of my worthiness, I could somehow convince myself I was worthy.
Spoiler alert: Sleeping with mentally abusive assholes who detested my style, career, and lewd sense of humor didn’t make me suddenly hold myself in high regard. Not. At. All.
On the contrary, it rendered my confidence battered and bloodied. I had to see my non-insurance accepting therapist twice a week for two whole years to get rid of my dark attraction to mean, manipulative narcissists!
Of course, it wasn’t just mean, manipulative narcissists I got down and dirty with, but that’s one of the major types I gravitated to.
Here is a list of seven types of women I wish I hadn’t slept with in my 20s.
1. The lesbian misogynist.
“I can’t believe you’re so smart!” exclaimed a woman I had met on Tinder halfway through our first date.
“Come again?” I asked, certain I hadn’t heard her correctly.
She tugged at the frayed flannel of her shirtsleeves. “I mean you’re like so over the top girly! All that red lipstick and those high heels. I didn’t expect you to know so much about politics,” she cackled.
I wish I could say that I told her to go f*ck herself. Instead, I actually slept with her that night. Why? Oh, maybe because I was a self-destructive masochist who hadn’t quite yet learned this hard, sad truth: Women can be as wildly misogynistic as men.
2. The body-shaming fitness addict.
“Aww, you’re so cute,” cooed a woman I was rolling around in the sheets with, as she tugged on the loose flesh of my upper arm. I was speechless. Horrified. I was 20 years old. I was naked. In bed. With the 31-year-old spin class instructor I’d been lusting after on MySpace for the past six months. And she was playing with my arm-fat. Did I mention I was also in the thick of a dangerous eating disorder at the time?
“You’re not fat,” she spat, reading my mind (beware, girls, body-shamers are a f*cked up breed that can totally read minds). “You’re skinny fat!” she chuckled.
That was ten years ago. Had I been the empowered woman then that I am today (I credit a decade of therapy), I would’ve shimmied back into my pleather pants, strapped my platform boots to my feet and stomped out of her West Hollywood studio apartment, never looking back. But because I was a manically depressed and bulimic baby dyke, new to the wildly intimidating LA lesbian scene, I laughed and let her go down on me. (She didn’t even get me off!) The only reprieve: I didn’t go down on her. I wish I could say it was because she didn’t deserve the efforts of cunnilingus, but in truth, I was simply too scared to venture down south. Oh well! One woman’s loss of an orgasm is another woman’s gain of dignity, darling.
3. The Cheapo.
There is nothing on this planet less sexy than a cheap bitch. Just because we’re both women doesn’t mean that the sweetness of romance flies out the window, and we all have to pay for ourselves! Ew!
While I’m completely against the concept of splitting the bill, there’s something even worse than splitting the bill, ladies. (Allow me to insert an official “trigger warning” to princess dykes who expect to be pampered, like GO magazine’s very own Dayna Troisi.) It’s when the person you’re on a date with makes a point to order the cheapest thing on the menu—like the garden salad, gag!—and then proceeds to calculate exactly what they’ve spent down to the penny. My vagina just closed at the mere thought of this unsexy scenario. If you’re that worried about money, don’t agree to go on a date at a restaurant in New York! Take her on a goddamn picnic in the park or something. (Bitches love picnics.)
I’m ashamed to say I’ve slept with a cheapo. Thankfully, only once. And to my credit, she was a one night stand, so I didn’t know she was a cheap dyke until the next morning at breakfast. I never slept with her ever again. Because the orgasms I’ll provide you with are worth gold, baby. And someone who won’t even treat you to $1 cup of coffee isn’t someone who appreciates the epic beauty of gold. That much I know, for sure.
4. The “Social Justice Warrior” who has never set foot outside her $50,000 per year liberal arts college.
Gahhh! I have a visceral, guttural reaction to this breed of lesbian. The out of touch “Social Justice Warrior” makes me want to peel the flesh off my body and run for the hills, skinless.
I mean, is there anything more painfully annoying in this cruel, cold world than a self-righteous person who wants to lecture you about “why drag queens are damaging to the culture” when they’ve literally never been immersed in the culture? When all they’ve ever done is bark about issues they’ve had no hands-on experience with to their equally annoying classmates in the safe confines of some exorbitantly expensive, New England liberal arts college? Newsflash: You’re not an authority on queer culture if you’ve never even set foot in a gay club, OK? Your “gender studies” class at Sarah Lawrence is not a gay club!
Since I didn’t go to a liberal arts college and was basically reared at my local gay club, I don’t often come across this type of lez, let alone sleep with her. But alas, at 21, I visited a high school friend at Wesleyan college, did my first fireball shot, and one thing led to another…
5. The girl who is ready to get married and have cats with you after the first hookup.
Look, I can’t throw *too much* shade at the girl who confuses mind-blowing sex with soul-mate-worthy love, because, shit, I’ve been that girl. Twice.
However. Karma is not a bitch, but rather a smart, business-savvy lesbian who will always give you whatever you’ve dished out. Exactly one year after I shamelessly stalked the poor one-night-stand who gave me multiple orgasms, I was cursed with a relentless love addict of my own.
She wrote mile-long love letters, sent expensive throw pillows to my apartment, and blew up my phone so many times I feared it was going to combust into a million little pieces. And this was after only one lackluster romp!
Those throw pillows were chic, though. I still have them. (Shhh…don’t tell my fiancee).
6. The girl who accidentally moves in with you.
For the record, I haven’t actually slept with a girl who lowkey moved in with me. But one of my dear friends did, and I truly feel compelled to share her story with all of you. Think of it as a cautionary tale…
“It was our third date the first time she slept over. I found it odd that she always had a large JanSport backpack at every date; I figured she was just coming from work or something. But then, I’d always get a midday text: “What are you up to tonight?” I was new to the city, so usually, it was absolutely nothing. We’d grab dinner or drinks. She was a lush, and we’d toss back drinks before catching a cab to my apartment, every night after that first sleepover. It took me a few weeks before I realized I had spent every single night with her. At my apartment. Never hers. She had moved in with me without my knowing! The relationship imploded soon after because that is honestly a recipe for disaster.”
Steer clear of girls who carry overnight bags to dates. You’re welcome.
7. The girl who isn’t over her ex.
Of all the shitty women I wish I hadn’t slept with, the most demoralizing sex sessions I’ve endured are the countless times I’ve put out for a dyke who is still majorly hung up on her ex. Once I had a girl cry after I gave her an earth-shattering orgasm. “I just, just, just, just miss, miss, miss her!” she howled, as snot catapulted out of her nose. Another time, a girl dramatically halted a steamy sex session. “I CAN’T!” she yelped, pulling her jeans up. “I’M STILL IN LOVE WITH CINDY!” She ran out of my apartment so quickly she left her $600 Rag & Bone jacket on my bed (you know I looked up the price). It’s bad when a lesbian leaves her beloved leather behind.
So if you’re having a tough day, honey, I want you to relax those stiff shoulders. At least you didn’t make a girl run out of your apartment faster than a jaguar leaping through the night, in the middle of sex!
But guess what? Despite this laundry list of cringe-worthy moments I’ve bestowed upon you, I’m still standing. The embarrassment, the shame, the regret you can experience associated with sex can be so intense, it feels as if it can knock your fragile body to the ground! And sometimes it does knock you to the ground. But you know what the beautiful thing is? You can dust off your gorgeous knee-caps and get right back up. You’re so much stronger than you think you are.
So if you’re spiraling over someone you’ve slept with, I urge you to release yourself from those shackles of shame, babe. In fact, celebrate your sex fails as vivaciously as you celebrate your sex wins. Because you’re much more of an interesting, nuanced person for having nose-dived into such a bevy of wild experiences!
Now smile, delete the numbers of all the women you don’t want to sleep with again, and strut out into the streets with confidence. Armed with all of your dark dating experiences, you’ll have excellent content for a bestselling memoir. And one day, you’ll be laughing all the way to the bank, babe.