15 Times Awkward Made Us Cry

Photo: Courtesy of MTV.
On Awkward, Jenna Hamilton (Ashley Rickards) is known as "that girl." She's the one who tried to take her own life. Although, instead of being treated with kid gloves, her peers at Palos Hills High look at her with a mixture of confusion and disdain. School mean girl and queen bee Sadie Saxton (Molly Tarlov) callously quips that Jenna should just finish the job. Jenna's best friends believe that it was an accident, but urge her to keep her head down until her moment in the spotlight is over, and someone else can take on the title of "that girl."

High school is hard, and over the past four seasons, Awkward has done a bang-up job capturing just how cruel and exasperating, but also wonderful, it can be. The show doesn't sugarcoat its protagonist or her experiences. Jenna can be selfish — she's cheated on her boyfriend Matty (Beau Mirchoff), dabbled with drugs, and despite being a great writer, doesn't have the grades to get into the college of her dreams. It rings true to what it's like to be a teenager, and at times, it can be heartbreaking to watch Jenna and her friends struggle to make sense of it all.

The show returns for its fifth and potentially final season August 31 on MTV. As Jenna, Matty, Tamara (Jillian Rose Reed), Jake (Brett Davern), and Sadie prepare to graduate and say goodbye to the hallowed halls of Palos Hills High, we took a look back at all the times Awkward made us tear up and have a good cry. Sing it with us: As we go on, we remember all the times we had together...
Advertisement
1 of 16
Photo: Courtesy of MTV.
This life truism. (Season 1, Episode 1, "Pilot")
Why do people think Jenna tried to kill herself in the first place? Because of this sentence she writes on her blog before she slips in her bathroom while taking aspirin, breaking her arm and throwing a hair dryer into a full bathtub in the process.
2 of 16
Photo: Courtesy of MTV.
"Nobody can know that I like you." (Season 1, Episode 1, "Pilot")
That's what Matty says after having sex with Jenna for the first time, which he doesn't know is also her first time. She asks if he wants to go to sophomore orientation together, and that's when he delivers this cutting blow. Way harsh, McKibben.
Advertisement
3 of 16
Photo: Courtesy of MTV.
The "carefrontation" letter (Season 1, Episode 1, "Pilot")
This letter, which is signed "A Friend," is another reason Jenna is having the worst day of her life when she blogs that "being a teenager makes you want to die."
4 of 16
Photo: Courtesy of MTV.
(Season 1, Episode 6, "Queen Bee-atches")
This episode peels back Sadie Saxton's Mean Girl-inspired girl exterior to reveal the insecurities within that drive her to act the way she does.
5 of 16
Photo: Courtesy of MTV.
Jenna stands up to Matty. (Season 1, Episode 7, "Over My Dead Body")
"So you can sleep with me in private, but you can't talk to me in public?"
6 of 16
Photo: Courtesy of MTV.
Jenna's birthday (Season 1, Episode 9, "My Super Bittersweet Sixteen")
Jenna's 16th birthday is a bit of a disaster. Her guidance counselor (Desi Lydic) brings her a cake in the middle of the cafeteria, her mom redoes her bedroom so it's devoid of any personality, and Sadie spills coffee all over her. Jenna ends up crying, but also has a moment of realization when she decides that what doesn't kill you makes you stronger.
7 of 16
Photo: Courtesy of MTV.
Lacey's tearful confession. (Season 1, Episode 12, "Fateful")
Even though Awkward is a teen show, the adults in it have changed a lot since the first episode, too. Perhaps no one more than Jenna's mother, Lacey (Nikki Deloach).
Advertisement
8 of 16
Photo: Courtesy of MTV.
Matty confesses his love for Jenna. (Season 2, Episode 2, "Sex, Lies, and the Sanctuary")
Of course, it's only after Jenna starts going out with his best friend, Jake.
9 of 16
Photo: Courtesy of MTV.
Jakara in love. (Season 3, Episode 1, "Cha-Cha-Cha-Changes")
At the end of season two, Jenna chooses to spend the summer with Matty instead of going to Europe with her friends. She doesn't speak to Tamara all summer, and when the group heads back to school, Jenna finds out that her best friend is now dating her ex-boyfriend, Jake. They love making out in front of people.
10 of 16
Photo: Courtesy of MTV.
Jenna cheats on Matty. (Season 3, Episode 10, "Redefining Jenna")
She can't resist the allure of sexy Collin (Nolan Funk) from her creative writing class.
11 of 16
Photo: Courtesy of MTV.
"I was slumming it with you." (Season 3, Episode 14, "The Bad Seed")
Even though Jenna cheats on him, there's no need for Matty to say this to her.
12 of 16
Photo: Courtesy of MTV.
Val gets fired. (Season 3, Episode 18, "Old Jenna")
Jenna is Val's girl...until Jenna gets her fired after writing a defamatory story about the school guidance counselor in the literary journal. Val doesn't take her dismissal or Jenna's rejection of all her past support and friendship well.
Advertisement
13 of 16
Photo: Courtesy of MTV.
Ming's disappearance. (Season 4, Episode 1, "No Woman Is an Island")
Sure, they explained it with “she went to boarding school,” and we knew actress Jessica Lu wanted to move on, but it’s always sad when a best friend just ups and leaves and is never heard from again in this time of Facebook, Snapchat, and unlimited texting.
14 of 16
Photo: Courtesy of MTV.
"Tamara Never Comes" (Season 4, Episode 3, "Touched by an Angel")
Breakups are already hard, but Tamara's gets infinitely worse when Jake insists on singing about her trouble reaching orgasm in front of the entire school. He claims the correct lyric is "Tomorrow never comes," but he's clearly saying "Tamara."
15 of 16
Eva (in general) with Matty, specifically. (Season 4, Episode 10, "Snow Job (Part 1)"
From the moment she's introduced, Eva is suspect. When she starts dating Matty and rubbing it in Jenna's face, she officially becomes the worst.
16 of 16
Like this post? There's more. Get tons of entertainment news, celebrity updates, and cat videos on the Refinery29 Entertainment Facebook page. Like us on Facebook — we'll see you there!
Advertisement

More from TV

Watch

R29 Original Series