Pen15: 13 Cringey Moments We Can’t Dislodge From Our Brains

Relive the worst years of your life all over again.
Pen15: 13 Cringey Moments We Can’t Dislodge From Our Brains

Pen15 is like a sillier version of Bo Burnham's Eighth Grade, with all of the truth and heart still stuffed in. Along with that truth comes the realization that we all were as oblivious as these teens, making us cringe in self-embarrassment. Here are 15 hilariously cringe-worthy moments from the 'teens' at Pen15.

The Timpani Solo

Pen15 solo


When Maya lies to her touring father about having an upcoming solo in a band recital, he changes his schedule to come home early and cheer on his girl. Maya decides to stick with the lie and gives HERSELF a solo in the show, pulling out all the stops including screaming, chanting, and vomiting.

The Thong-Nappers

Pen15 Thong


Maya and Anna steal the thong of the most popular girl in school, Heather. The two are obsessed with the power the thong gives them, empowering their womanhood and confidence. It gets a little awkward once the girls start doing things like deeply inhaling panties and flaunting their whale tails. These scenes are hilarious and watching two adults give/receive an atomic thong wedgie adds to the charm.

Anna and Brendan’s Make-Out

Pen15 makeout


We are given a wildly intimate close-up of Anna’s makeout session with her first boyfriend, Brendan. The sound design is wet, and the visuals are nothing pretty to look at. This scene is about 30 seconds but felt like ten minutes. And yes, it still seems all too familiar.

Anna Solves Racism

Pen15 racism


When Maya is forced to play a Mexican gardener in a video because she and Mexicans are both “tan” and “different,” Anna takes it upon herself to step in and solve racism. She does a few hours of internet research later that night and stages an impromptu performance that features racism in the school halls, at Maya’s expense. Watching Anna contextualize racism from the viewpoint of a person of color is cringey to the max, but the stage fight these two perform when they make up is well worth it.

Maya Learns The Mysteries Of Her Body

A particular episode chronicles Maya’s discovery of masturbation when she made her My Little Pony dolls kiss each other. Maya becomes obsessed with masturbating and even starts doing it several times at school. The episode highlights the difference between how early sexuality is treated differently between boys and girls and is so accurate, it makes you feel like you’re reliving the worst years of your life.

Kissing Lessons

Pen15 practice kissing


At one point the two decide to practice their kissing on Anna’s bedposts. The two adult actresses give it everything they’ve got to lick these bedposts clean. Before too long Maya is rubbing the bra she is wearing over her shirt on the bedpost, only for the two to be walked in on by Anna’s dad. 

Parents walking in while I’m doing something private is a skill I’d say I’ve mastered.

Getting Rejected At The Dance

Being rejected at a school dance is a rite of passage. For every 10 kids that approach another, there's at least one that will be met with a group of girls laughing and running away, at least in my experience.  When Anna asks Alex to slow dance he politely says “no” without a second thought, a hilarious delivery, providing another stinging reminder of our youth.

Feeling Grown Up

Pen15 little boy


Anna’s interaction with a boy before nearly buying five lighters for a single cigarette:

“Sup, here with your mom? We’re here alone, b**ch. JK, but we are here alone.”

The Giant Tampon

Pen15 giant tampon


In the midst of an argument between both her mom and her best friend, Maya gets her first period with no one to turn to. In a hilarious visual gag representative of adolescent fear, Maya’s tampon grows and grows until it's cartoonishly huge, mimicking the amount of pressure Maya feels using it.

The AIM Names

When Viper911 is taken as an AIM screen name already, Maya opts in for the name “Diper911” saying it’s still cool. Anna chooses the laid-back name of “BabySpice666.”

This brings back memories of realizing I needed a new username when I had to tell the GameStop employees they could reach me at

Process Of Elimination Make Out

Pen15 lineup


When Anna and Maya show up at a make-out party, they learn that five boys will match up with the five girls. Unfortunately, the pairing up goes back to kickball rules, where the boys pick out which girl they want. It’s sad but memorable. (At least you weren’t paired up with a kid way younger than you like Anna.)

The Dance Away From The Kiss

Pen15 hangman


When Maya is too scared to kiss in the closet at the make-out party she starts avoiding the boy's lips like the plague… or cooties. The first escape from the kiss is a “dragon” dance out of the way, and the second includes my favorite line “Hoot hoot. I’m an owl now.”

Standing Up To The Bully

After Maya is deemed “UGIS” or “The Ugliest Girl In School,” she devises a plan to publicly humiliate her bully after school and spreads the word about her upcoming roast. When the two start insulting each other Maya gets a little heat then flames him with the classic “you’ve got an aardvark d*ck and that’s why your dad died.”

So wrong it's right.

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