Pen15: 10 Most Cringey Moments


Schoolyard pick make out session

It's usually around adolescence that we start feeling attraction towards other people, and a desire to feel attractive ourselves; which is ironic, because puberty has a way of making us feel anything but. Thus, we seek validation from others finding us attractive.

When Anna and Maya hang out with the "cool girls," their new friends invite some boys over and they subject themselves to allowing the boys to pick which girl to make out with, schoolyard style.


You know it's going to end badly before it even starts, with poor Anna being picked last by a young boy who she'd be more likely to babysit than make out with.

Desperate for the coolest IM handle

Kids today with their smartphones will never know the agony and the ecstasy of instant messaging. Us tweens would race home from school, fire up our dial-up internet and log on to AIM or MSN...just to talk to the kids we spent all day with.

Of course, finding the perfect handle was key.


Often we would pick something way too racy for our age, sending any parent who watched Dateline into a panic. Hence, Maya knew she found the perfect AIM name in "Viper911"...except someone else thought of it first. So as a backup, she unwittingly picked the most unsexy user name ever — "Diper911."

Haircut hack job

The dawn of a new school year means many thing: crisp notebooks, new pencil cases, and a chance to change your image. When Anna tells Maya she doesn't think she changed much over the summer, Maya goes into a tailspin.


But she quickly finds a solution to her woes — a new, layered haircut, à la Sarah Michelle Gellar.

As it's the night before the first day of school, Maya doesn't exactly have time to book an appointment with a hairdresser. But that's what scissors are for! The result is an uneven mess that looks like she cut her hair with her eyes closed. So her mom "fixes" it by plunking a bowl on Maya's head and giving her the worst haircut known to humankind — the bowl cut. So, Maya has to start her first day of the seventh grade looking like a mushroom.

Standing up to your bully...a little too well


Old-fashioned torture devices must have been invented by middleschoolers; it's insane how this demographic has the never-failing ability to dream up creative ways to be cruel to each other. At Maya and Anna's school, the boys award a yearly "UGIS" — Ugliest Girl in School. Maya's unfortunate haircut earns her the moniker.

Learning to stand up for yourself is a difficult tightrope to walk, especially at that age. To her credit, Maya gives it her all, publicly confronting the ringleader of victimizers.


She goes below the belt, literally, making fun of his genitals and doubles down on the low road by mocking the fact his dad is dead. What started off as an empowering "yas queen" moment is hindered by the orphaned bully bursting into tears.

Being rejected for a dance

When you're thirteen, putting yourself out there romantically has the stakes of trying to disarm a bomb intended to blow up the world. In fact, we'd prefer the bomb detonating over being rejected. But we also know that if we don't try, we likely won't get what we want.


If movies and TV have taught us anything, it's that romantic rejections are humiliating, loud, and public. But in reality, they're often a quiet shrugging off and that can hurt even more. When Anna works up the courage to ask her crush Alex to slow dance with her, he nonchalantly says "no" as if declining a piece of proffered gum. Ouch.

First kiss

Need we say more? Nothing sums up awkward like these two words. First kisses are sloppy, rubbery, heavy in drool and lacking in romance.


Anna experiences this with her first boyfriend, Brendan. While Anna is eager for new experiences, she's not exactly attracted to Brendan and this makes the situation even cringier.

The scene is shot in a hilarious way. As Brady Allen, the actor playing Brendan, is a kid, he's not really kissing Anna Konkle. Though an adult body double is used, most of the kissing is alternating extreme close-ups of Anna and Brendan's mouths and facial expressions. Brendan's is a river of saliva and Anna's is full of the same perplexed discomfort as every viewer watching.

Racism via Spice Girls


The Spice Girls are a cultural touchstone for any millennial woman. Though we embraced "Girl Power" — and all its merchandise — with open arms, we were likely oblivious by the problematic othering of the group's only minority member. Mel B was labeled "Scary Spice" and let's be honest, she was likely most girls' least favorite member of the group.

When Anna and Maya are working on a project with the popular girls, they dress as the Spice Girls for a video about osteoporosis — because, why not? Though Maya wants to be Posh Spice, the other girls insist she be Scary because she's the only racial minority.


If that's not icky enough, they also insist she act out a slew of offensive racial stereotypes. Maya is caught between not wanting to demean herself but wanting to please the popular girls. She chooses the latter, and it's painful to watch.

Anna tries to end racism

Anna is present for the unsettling Spice Girls incident and later gets called out for her complicity by Maya's brother. This makes Anna feel terrible, so she gives herself an Ask Jeeves crash course in racism. She decides to make it up to Maya by trying to end racism with a hunger strike and a tacky demonstration that alienates Maya even more.


Ultimately, Anna's trying to do the right thing, but she goes about in entirely the wrong way. As she's not a racial minority herself, instead of being vocal, Anna should offer an ear to Maya and allow her to speak for herself.

The giant tampon

Your first period has a way of debuting at exactly the wrong time. This happens to Maya, right when she's feuding with both her mom and Anna. With nobody to turn to, Maya keeps quiet about this adolescent milestone.

As adolescent girls, we're often not familiar with the intimate parts of our bodies and the prospect of using a tampon for the first time is intimidating, to say the least.


As Maya tries to rally herself to use it, we see what it's like through her eyes, as the tampon goes from normal-size to slightly exaggerated to cartoonishly huge. It's a funny joke, but we remember what it was like...and it certainly wasn't funny then.

Sharing a stolen thong

As discussed, body issues abound when you're in middle school. If we had a magic pill that could make us feel more desirable, we'd take it in a heartbeat. Anna and Maya discover the next best thing — popular girl Heather's thong.


They steal it when Heather is changing and take turns wearing it to school. Though there are multiple shots of the girls washing the thong before passing it off, they're still wearing stolen underwear. *Shudder* And yet, we get it. It all comes back to the desire to feel sexy. Alas, the plan backfires when Heather suspects Anna and Maya stole the thong. This leads to a comedic series of events that ends in a pantsing at a seniors' home and nothing is worth that — not even a pink thong.