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VOICE OVER: Rebecca Brayton WRITTEN BY: Cassondra Feltus
"Big Mouth" is always awkward but these moments are downright painful. For this list, we'll be looking at the most uncomfortable, embarrassing, and cringey moments in Netflix's coming-of-age sitcom. Our countdown includes Jessi's first period, Andrew making a mess at the dance, Missy kissing Jessi's dog, Nick getting pantsed, and more!
"Big Mouth" is always awkward but these moments are downright painful. For this list, we’ll be looking at the most uncomfortable, embarrassing, and cringey moments in Netflix’s coming-of-age sitcom. Our countdown includes Jessi's first period, Andrew making a mess at the dance, Missy kissing Jessi's dog, Nick getting pantsed, and more! What moment made you squirm the most? Let us know in the comments.

#10: Andrew’s Camp Constipation

“Poop Madness” Using public restrooms is often uncomfortable, especially when it comes to going number two. In one of the show’s more disgusting episodes, Andrew’s bathroom anxiety prevents him from “going” the entire time he’s at camp. As one can imagine, the result is seriously painful. On the last night of camp, Andrew retreats to the woods, where he goes on a psychedelic journey with talking creatures. When his stomach finally erupts, Nick is there to coach Andrew through the “birth.” And surprise — it’s twins! But the worst awkwardness comes when everyone at the camp stumbles upon this gross sight. Neither Andrew nor Nick will ever live that down.

#9: Missy Kisses Jessi’s Dog

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“Sleepover: A Harrowing Ordeal of Emotional Brutality” When Jessi throws a slumber party and invites popular girls Devin and Lola, she also welcomes her nerdy friend Missy, who hasn’t been to a sleepover before. Missy’s parents don’t let her have sugar, and we find out why. Sugar brings out another side of Missy — an aggressive, frenetic, uninhibited side. We’re glad Missy gets to let loose and try soda for the first time, but unfortunately, she ends up embarrassing herself. Jessi’s dog happens to resemble Nathan Fillion, Missy’s number crush and subject of her dreams. She hallucinates a flirty exchange with the star and the two start making out. But she’s actually kissing the dog. Of course, Lola is right there with her phone to capture it all.

#8: Jessi Talks to Judd

“How To Have An Orgasm” Kids, teens, and adults can all relate to having awkward interactions. Suddenly your brain and mouth stop working together, and words just aren’t coming out right. And when you’re talking to someone you find attractive, the awkwardness is nearly tripled. This is what happens to Jessi when she runs into Judd, Nick’s older brother whom she has a major crush on. Jessi seems to have this problem a lot. As soon as she’s around someone she likes or is trying to impress, she starts talking in weird voices and speaking Spanish. Jessi really needs to take Connie’s advice.

#7: Nick Gets Pantsed

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“Steve the Virgin” While on an already pretty awful double date, Lola demands that Andrew pants her, because it’s “National Pantsing Week.” When he refuses, she runs around the mini golf course pantsing others to show him how easy it is. Lola launches herself in the air and yanks Nick’s pants down while he’s stuck on the zipline. Naturally, Nick is mortified - much to the delight of the Shame Wizard. And to make matters worse, his parents are there, too. They run to help him, but it just gets more awkward when his dad pulls down his pants in solidarity. This isn’t the first time he’s been ridiculed about his … proportions. And it won’t be the last. He just can’t catch a break.

#6: Andrew Gets Caught Kissing Cherry

“Florida” The Gloubermans (and Nick) head down to Florida to spend spring break with their family. Andrew and Nick are pretty bored until his cousin Cheryl (aka Cherry) shows up. Andrew finds his matured cousin attractive, and it seems like the feeling is mutual. Cherry is weirdly flirty, but Andrew can’t figure out if she’s messing with him or not. And honestly, we couldn’t either. But then Cherry takes him in their zeyde’s bedroom, tells him to imitate their deceased bubsie, and initiates a make out. Of course, that’s when the family walks in on them. But that’s not the end for the kissing cousins. Back home, Andrew gets caught sending private photos to Cherry. The humiliation never ends.

#5: Spa Day

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“What Is It About Boobs?” Many kids feel embarrassed by their parents. But Missy’s mom takes it to a whole other level in this season two episode. After she overhears the girls lamenting their body insecurities, Mrs. Foreman-Greenwald decides to take Missy and Jessi to a naked spa. As soon as she disrobes, the girls are immediately uncomfortable, as one would expect. We’re all about body positivity, but this little field trip might’ve been a little too jarring for two middle school girls. And if she wasn’t already mortified, Jessi runs into her mom’s girlfriend. Connie’s body-loving disco tune makes the awkwardness worth it, though. We think…

#4: Andrew Makes a Mess at the Dance

“Ejaculation” Going through puberty means uncontrollable urges, which Andrew Glouberman is very familiar with. In the show’s first episode, appropriately titled “Ejaculation,” the middle schoolers go to a dance. With Maury around, Andrew thinks about sex on the regular. So, when he dances with Missy, well, you could say things get hard for him. He can’t help himself and has an “accident” in his pants. Andrew rushes to the bathroom where it gets even messier. Luckily, Nick helps him out and they’re able to laugh about it. This is only the first of many, many more embarrassing situations.

#3: Andrew at the Funeral

“The Funeral” Yes, this is the fourth entry with Andrew at the center of a painfully awkward moment. If you thought him kissing his cousin was bad, then prepare yourself for this one. When Andrew doesn’t follow “the Glouberman Method” for the first time, something terrible happens. He overhears his dad say that his zeyde (his grandfather) died. And thinking that this change in his routine led to the death of a family member, he vows to avoid touching himself again. But at zeyde’s funeral, Maury and the ghost of zeyde encourage Andrew to “yoidle his doidle.” And where does he do this? Right next to the casket. Someone walking in on him was bound to happen. But his whole family? Yikes.

#2: Jessi’s First Period

“Everybody Bleeds” Puberty is a string of countless mortifying moments. And in the first season, Jessi goes through one of the worst. On a field trip to the Statue of Liberty, Jessi gets her first period. Of course, this is also the day that her mom suggested that she wear white shorts. When Andrew calls attention to the visible red stain, Jessi quickly realizes it’s the day she’s been dreading. The whole situation is an absolute nightmare. Not only is there no toilet paper in the bathroom, but she has to ask her guy friend for help. We do admire Andrew for lending a helping hand, though. Unfortunately, she’ll suffer another huge embarrassment at camp ... Before we unveil our top pick, here are a few honorable mentions.

Leah Walks in on Andrew Pleasuring Himself, “The Shame Wizard”

Andrew’s Caught With His Pants Down Yet Again

Nick’s Embarrassing Parents, Various

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The Birches Can Be Just a Little Too Open Around Their Kids

Jay Tells Lola His Feelings, “Horrority House”

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Unrequited Love Is Peak Awkwardness

Nick Bombs at the Camp Talent Show, “Poop Madness”

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Top 10 Times Nick Was the Best Character on New Girl

The Secondhand Embarrassment Is Real With This One

#1: Missy’s Worm Squirm

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“Dark Side of the Boob” Missy brings her glo worm Wiggles to the school sleepover, which turns out to be a grave mistake. She naps while everyone else is still awake and starts “dancing” with her worm. Everyone crowds around her and laughs, and when she wakes up, Missy is beyond horrified. The Shame Wizard is there to make her (and everyone else) feel bad about themselves, which leads her to toss Wiggles in the trash. Thankfully, the kids “defeat” the Shame Wizard and have an all-out “no shame” party. Missy’s able to squirm with her worm once again. Though we’d suggest that she keep this activity in her bedroom from now on.

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