7 Hilarious ‘Pen15’ Moments That Will Also Make You Cringe

Annakonkle-mayaerksine-pen15
Alex Lombardi/Hulu

As Y2K nostalgia runs rampant in today’s culture, we often neglect to remember the cringe parts of that time. However, Pen15 deglamorizes the early 2000s through painful-to-watch scenarios of middle school that make Millennials remember all of their pre-teen traumas.

Creators and executive producers Anna Konkle and Maya Erskine play themselves as 13-year-old social outcasts surrounded by child actors. Hulu’s rated-R cringe comedy follows Anna and Maya’s friendship as they experience the brutal world that is middle school—and these two comedic geniuses know how to make you laugh while recoiling from the screen.

And what better way to celebrate Pen15 returning with seven new episodes Friday, December 3 than by highlighting seven of its cringiest moments? Scroll down to see which ones made the cut.

Pen15, Season 2 Part 2 Premiere, Friday, December 3, Hulu

Anna Konkle as Anna and Maya Erskine as Maya in Pen15
Alex Lombardi / Hulu

Tragic Trends of the Early 2000s

The costumes on this show are a Millennial’s worst nightmare, perfectly encapsulating the embarrassingly bad outfits from the early 2000s that have now aged like milk. We see Maya and Anna in unflattering khaki skirts, polo tops, lace jeans, and cat graphic tees. Maya sports an unfortunate bob haircut while Anna consistently wears a ponytail with two strands hanging in the front. During your binge, you can spot the numerous details that capture the hilarity of bad Y2K fashion layered with the familiar discomfort of pre-teen expression. 

Maya Erskine as Maya in Pen15
Alex Lombardi / Hulu

Sisterhood of the Traveling Thong

Maya and Anna steal a thong from the school’s Queen Bee, Heather (Anna Pniowsky). They both take turns wearing the underwear—rarely sanitizing it—and discretely hand it to each other in public like it’s a drug deal. Maya and Anna outlandishly perceive this thong as the key to womanhood, as they strut around school with it on and keep score of how many kids take a peek at their behinds. Once the thong’s power interferes with their friendship, they have no choice but to set it free—well, Anna  forcefully takes it off Maya.

Anna Konkle as Anna in Pen15
Alex Lombardi / Hulu

Anna's Social Activism

During a group project, Maya faces racial micro-aggressions from other girls and Anna stays silent. No longer wanting to be complicit, Anna does a night’s worth of research on racism and acts as if she’s the only solution for social justice in her school. She looks at her peers, demanding they “wake up,” and hilariously holds a mirror to their faces in hopes they take a hard look at themselves. She goes on an outrageously brief hunger strike. She even attempts to lead a public demonstration—which backfires and makes her look even more bigoted. Anna eventually learns that these types of subjects are more complex than one night of research and chooses to listen to Maya, an actual person of color, rather than herself.

Maya Erskine as Maya in Pen15
Hulu

Y2K Internet Slang Culture

Do you remember how hard it was to get the perfect AOL screen name? Well, Maya (Diper911) and Anna (Babyspice666) lock theirs down. Pen15 takes us back with Y2K internet culture—and it’s awfully cringeworthy. Characters will spell words like busy as “bizzy” and create acronyms like WUWU (Wuz Up With You). They also use the away message feature on AIM with melodramatic Mark McGrath lyrics or Keanu Reeves quotes that are specially curated for attention—the original form of subtweeting.

Maya Erskine as Maya and Anna Konkle as Anna in Pen15
Alex Lombardi / Hulu

First Kisses

Not everyone wants to remember their first kiss, but absolutely no one wants to remember how they practiced beforehand. Maya and Anna spend a lot of time roleplaying sexually-charged scenarios and rehearsing tongue movements on their furniture. We are also forced to watch a disturbing close-up shot of Anna’s make-out session with Brendan (Brady Allen), which involves a concerning amount of saliva. Anna describes the disappointing experience to Maya as “he put his tongue in my mouth and did a torpedo cat tongue and like, drilled my mouth.” It’s perfectly normal to not know what you’re doing at that age, but the sad reality is, some people still kiss like that beyond middle school.

Maya Erskine as Maya in pen15
Hulu

Maya's "Me-Time"

Leave it up to the brilliant writers of Pen15 to show comically honest depictions of female puberty on television. When playing with her My Little Pony dolls, Maya has her first masturbatory experience and after that, she is turned on by the phallic shapes of sand dunes. Eventually, the act consumes her and she can’t stay away from doing it during school. Although uncomfortable to watch, Maya’s journey with self-pleasure brings up an important conversation on the stigmas of female puberty and how it should be normalized, rather than kept hidden.

Maya Erskine as Maya and Anna Konkle as Anna in Pen15
Hulu

Middle School Relationships

Nothing says friend bonding more than being groped together! At the school dance, the popular Brandt (Jonah Beres) asks to “finger” Maya in the janitor’s closet and she brings Anna for emotional support. Maya and Anna ask for him to go to “second base” instead and Brandt then awkwardly rubs their breasts in rough circular motions. He immediately leaves after, but before he does, he and Maya impulsively say “I love you” to each other — only for him to ignore her after and pretend like this never happened, the future of chivalry!