30 Rookie Lesbian Dating Mistakes I Made Before 30

Every time you go the bathroom with the door open, a lesbian angel loses her wings.

I’ll never forget the first classic lesbian mistake I ever made. I was puffing on a cigarette outside of a lesbian club, looking all bleary-eyed and angst-ridden when an older dyke, probably about fifteen years my senior, came sauntering on over to me.

“What’s her name?” She asked me, leaning up against the graffitied cement wall, pulling a lighter out of her back pocket like some sort of 1940s swashbuckler.


“Oh, honey.” The mystery lesbian said. “It’s clear you’re upset about a girl.” She looked me long and hard in the eyes and dramatically raised her bushy left brow. “I know that expression.”

I stamped out my cigarette. “It’s that obvious?” I squeaked.

She lit her cigarette and sucked back an impressive drag of smoke. “Yes.”

I sighed. “Fine. None of my friends will talk to me because I drunkenly hooked up with one of their exes.” I gazed into my filthy Converse sneakers wondering how the hell they got so dirty. Had I blacked out and gone hiking?

A slow smile stretched itself across the mystery lesbian’s weathered-looking face. “Rookie mistake.”

“I don’t see what the big deal is! They’ve been broken up for two f*cking years!” I practically spat.

“Look, kiddo. Don’t shit where you eat.” And just like that, she was gone. I could hear her chuckling to herself as she happily waddled back into the bar, leaving me to stew in the nervous sweats of my “rookie mistake.”

That might have been the first rookie mistake I made when it came to the mysterious underworld of lesbian love and sex, but let me assure you, it certainly wasn’t the last. I don’t know about you queers, but it took me a long time to understand the intricate rules of the ever-complicated girl-on-girl dating scene.

Here are 30 rookie mistakes I made, that I finally stopped making by the time I hit 30 and became the seasoned lesbian I am today. (Though I *might* have the occasional slip-up, but shh).

I swear to Lana Del Rey.

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Oh, and baby gays, please learn from my mistakes. I throw myself under the bus and make myself an un-dateable, red-flag-waving lesbian so YOU can have a better dating life than I ever did.

1. Catching feelings for a girl with a boyfriend.

This only leads to a smashed heart, a life-long distaste for all heterosexual-man-kind, and epic disappointment. I made this mistake in high school and I’m convinced it screwed me up for life.

PSA: Ladies, ladies, ladies. Do not fall for a girl with a boyfriend. You’ll get yourself into all kinds of trouble. At least wait until after they break-up and she’s sure she wants to do more than just “practice kissing” with you.

2. Hooking-up with a friend’s ex.

The older lesbian friend that laughed at me during that life-changing night at the bar was right. “Don’t shit where you eat, kiddo.”

Seriously, “kiddo,” don’t do it. I know it feels like there are only ten attractive lesbians in your city and nine of them have dated one of your friends, but either score the one lesbian who hasn’t, or date outside of your city.

Hell hath no fury like a lesbian scorned by one of her Sapphic friends. That grudge will last a lifetime.

3. Hooking up with a friend of a friend’s ex.

I don’t care if the girl you like is a friend of a friend of a friend of a friend of a friend. If she’s in any way tethered to a dyke you care about, stay far, far away.

We are a fierce lesbian tribe. Upset one of us, upset all of us, baby.

(I know, I know. It sucks. This is why I prefer to date long-distance; there isn’t local baggage to stress over.)

4. Trusting a f*ckboi.

If she looks like a Shane, talks like a Shane, and walks like a Shane, chances are she’s a Shane.

5. Assuming that because she’s a girl, it’s impossible for her to be a f*ckboi.

I don’t care if she’s a butch, a femme, a stem, a stud, a lipstick lesbian, a mascara lesbian or a chapstick lesbian—just because she’s a self-identified girl doesn’t mean she can’t be a f*ckboi. F*ckbois come in all shapes, sizes, and styles.

6. Hooking up with a bartender of my favorite bar.

It will eventually fall apart and get awkward and you, my sweet darling, will never be able to enter your favorite bar again, without needing to A) pop a Xanax (which is a terrible idea if you’re drinking) or B) take three tequila shots (which is a terrible idea in general).

7. U-Hauling.

I promised myself I would never be the lesbian who u-hauled until I became the lesbian who u-hauled. Now I’m the lesbian who has officially never lasted a lease.

8. Signing leases against my better judgment.

Speaking of leases, the number of times I’ve dutifully signed that godforsaken dotted line when my instincts were screaming “Don’t do it! This bitch is insane!” is unfortunate, to say the least.

9. Wearing my girlfriend’s leggings.

“Are you wearing my leggings?!” My girlfriend mouthed to me after showing up late to a yoga class. I was in downward dog trying to center myself. “What’s the problem?” I mouthed back.

“We can’t share leggings! It’s unsexy!” She said out loud, startling the Republican lady resting in child’s pose to her left.

Truth be told, she’s right. Sharing leggings is the gateway drug to peeing with the door open. And you know, every time you pee with the door open in front of your girlfriend, a lesbian angel loses her wings.

10. Wearing my girlfriend’s jeans (without asking).

When you start getting in trouble for wearing your girlfriend’s $300 designer jeans without asking, you’re approaching sister status. Your girlfriend will scream at you like you’re her annoying little sister who steals all of her good shit. And ifgod forbidyou happen to look better than she does in her jeans, well, pretty soon she’ll start thinking of you as her annoying little sister who steals all of her good shit. There is nothing sexy about your girlfriend associating you with her younger sibling.

It’s a surefire way to never have sex again.

11. Using my girlfriend’s toothbrush.

When you start sharing a toothbrush, you lose your identity entirely. Before you know it you’ll become one of those creepy lesbian couples that have morphed into the same person. Preserve your individuality, and use your own toothbrush, please and thank you.

12. Flirting with my ex-girlfriend’s friends.

It’s a cheap thrill, but trust me. It’s terrible karma.

13. Telling my girlfriend that her friend was flirting with me.

If your girlfriend’s friend is subtly flirting with you, just pretend she’s being super friendly and never, ever drunkenly tell your girlfriend.

Unless you want to be at the center of the lesbian drama, that is. Which, yes, can be fun for five minutes, but quickly becomes, uh, terrifying…

14. Changing my girlfriend’s style.

If you tell your girlfriend she looks sexier in blazers than she does in board shorts, she will resent you for the rest of your relationship.

Just keep your mouth shut and accept your babe for the board-short-sporting lesbian that she is, OR find an authentic blazer-wearing girlfriend. Because remember: you can’t turn board shorts into a blazer, no matter how hard you try.

(But you can, for the record, turn a housewife into a ho).

15. Writing articles about being a crazy girlfriend on the internet.

Not only have I written articles detailing what a crazy bitch I am, but I’ve been pissed off when girls I’m newly dating assume I’m a crazy bitch. “Well, didn’t you write about it on the internet?” They’ll ask.

Touché. Touché.

16. Pretending to know what lesbian sex was when I had no clue.

“Of course I know what lesbian sex is. It’s when um, you know. Like, when a girl gets on top of a girl…”

17. Pretending I knew how to scissor when I had no clue.

“I love scissoring!” I yelped at age 16 when I thought scissoring meant doing arts and crafts together.

18. Breaking up with my girlfriend when we were both on our periods.

Don’t make any sudden decisions when you’re both bleeding.

19. Being wildly jealous and possessive toward my girlfriend anytime another mascara lesbian/femme type entered the room.

If your girlfriend is going to flirt, she’s going to flirt. Acting like a deranged, hyper-jealous head case isn’t going to stop anyone from doing anything. In fact, it will only exacerbate her desire.

20. Flirting with female cops, TSA agents, security guards, and other women in uniform because I assumed they were gay.

I lust after a woman in a uniform, but sadly not all women in uniforms lust after me.


I love those long, pointy Lana Del Rey nails. However, my ex-girlfriend did not appreciate them when I attempted penetration with those fierce talons.

Oh, the sacrifices us fashion lezzies must make for sex! Luckily orgasms feel better than acrylic nails taste.

22. Faking an orgasm.

You might be able to fake orgasms with men, but you can’t fool your own gender, honey. Learned this one the hard way.

23. Unprotected sex, because, you know, “lesbians can’t get STIs.”

I’m amazed I made it out of my slutty phase (I say “slut” in an empowered way! Don’t worry!) without catching every STI under the sun.

I didn’t even know what a dental dam was when I was 21. I thought it was something they stuck in your mouth at the dentist. And I hate the dentist.

24. Playing into the “helpless femme” stereotype.

Just because society associates femininity with weakness doesn’t mean I have to play the role. Screw that. I wear heaps of mascara, look great in pale pink, AND can rescue myself from any kind of disaster.

25. Falling in love while wasted at lesbian parties.

“Owen, I’m in love” I once slurred to my best friend at the now-defunct Williamsburg gay bar “Sugarland.” The next morning I woke with my heart pounding and my mouth as dry as the Sahara desert.

I was suddenly flooded with embarrassing memories of pronouncing my love to a girl whose name or face I could not remember. For the next year, I lived in incessant fear of running into this girl again.


26. Calling my girlfriend my ex-girlfriend’s name.

Though I did find a great way to get out of this. If you call your girlfriend your ex-girlfriend’s name, just repeat the following:

“Oh babe, I’m SO sorry. I called you her name because I associate her with stress and I’m stressed right now! You never stress me out, which is why it feels foreign to say your beautiful name when I feel stressed.” Works like a charm.

“Only a lesbian could think of that,” my friend Kevin said to me when I told him how I got out of calling my girlfriend the wrong name. He’s not wrong.

27. Thinking I had a “type.”

I used to think that I liked girls with short hair who were taller than me. Now I realize I don’t discriminate.

Butch, femme, stem, tall, shortI like all kinds of lesbians (as the French would say, lesbiennes). Purr.

28. Playing hard to get.

I used to think if I blew off a date or didn’t text the girl I lusted over back, she would like me more. Then I realized that that game doesn’t work with women (at least not confident, mentally-stable women). It just makes her think that you’re a manipulative little twerp, and she doesn’t have time for that, OK?

29. Slipping up and telling a girl on the first Tinder date I had already looked at her Instagram.

“Oh, yeah, your cat, Fred! He’s soooo cute.”

“How do you know I have a cat named Fred?”

Crickets. Crickets. And more crickets.

30. Thinking the first girl I ever dated was the love of my life and that would I never get over her.

The first lesbian cut is the deepest, but I promise you, my heartbroken baby lesbians, you’re not supposed to end up with the first girl you date. In fact, you shouldn’t end up with the first girl you date. Your emotions are too out of whack, the stakes are too high. Plus, in order to know what you truly like, you need to get in there and date as many different ladies as you possibly can.

So dry those tears, babe. You’ll get over her. I big-sister-lesbian promise.

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