Cast and characters
Ashley Rickards as Jenna Hamilton, the titular "awkward" girl with an irreverent, optimistic outlook on life. The series begins with her receiving a brutal "care-frontation" letter that urges her to become less invisible. Jenna loses her virginity to and has a complicated on-off relationship with Matty McKibben. She is also an aspiring writer. Her best friends are Tamara Kaplan and (in earlier seasons) Ming Huang.
Beau Mirchoff as Matty McKibben, Jenna's main love interest. He initially appears to be a typical popular jock but over the course of the series reveals a deeper, more sensitive side. He struggles when he is out of his comfort zone, as he normally doesn't have to try very hard to be well-liked or accepted. He has a complicated relationship with his parents, and discovered he was adopted mid-series. He later meets his birth father, who, like Jenna's parents, had Matty at a very young age. Matty's best friend is Jake Rosati.
Nikki DeLoach as Lacey Hamilton, Jenna's young, appearance-obsessed mother who had Jenna as a teenager. She secretly wrote Jenna the brutal "care-frontation" letter in an ill-advised attempt to make her daughter more happy and popular. Once revealed, Jenna stopped speaking to her and Jenna's dad, Kevin, moved out of the family home. They later reconciled. She and Jenna seem to be polar opposites at times, but she has displayed genuine love and concern for her throughout the series. Her best friends are Ally Saxton and Val Marks.
Jillian Rose Reed as Tamara Kaplan, Jenna's best friend and a perky, type A personality who is as obsessed with her own brand of slang as she is with becoming popular. Tamara is seen as fun and outgoing but also often bossy and annoying because of her loud antics. A recurring theme of the series is Tamara succeeding much easier at being well-liked (as a cheerleader, then later as Sadie Saxton's friend) than Jenna. Like Jenna, she also tends to lead a disastrous love life.
Brett Davern as Jake Rosati, Matty's best friend and a brief love interest for Jenna. Jake is popular like Matty, but for different reasons; he's the class president, known for his smarts and tends to be well-liked by everyone for his caring nature. Later, Jake and Tamara date but break up over Tamara's personality. Jake goes through identity crises throughout the series, rejecting his goody two-shoes image to become a "cooler" singer and later as a "townie", electing to take a gap year from college to work in Palos Hills. His most frequent love interest is Lissa Miller.
Molly Tarlov as Sadie Saxton, one of the most popular girls in school, though mostly because everyone fears her. Sadie is known for wit, particularly when it comes to caustic barbs that are usually followed by a sarcastic "You're welcome". She has an immense dislike for Jenna, and the feeling is mutual. Later, her father goes to jail because of a Ponzi scheme and her family loses all their riches, with her mother eventually abandoning Sadie. Her only serious relationship is with Sergio and Austin, who likes her despite how cruel she can be.
Desi Lydic as Valerie Marks, the incompetent but well-intentioned guidance counselor at Palos Hills High. Jenna begins seeing her after her accident in the pilot is misinterpreted as a suicide attempt. Val displays extreme lapses in judgment both in her counseling of the students (particularly Jenna) as well as her own personal life. She sees Jenna as more of a close friend (often referring to her as "my girl") and later forms friendships with Lacey and Ally. Val dates a professional mascot named "Biggie". After the kids graduate, Val quits to "find herself".
Greer Grammer as Lissa Miller (seasons 3–5; recurring seasons 1–2), a dimwitted cheerleader and Sadie's best friend; though she often serves as a clueless sidekick, she is wise emotionally and often gives random but great advice. Lissa is deeply religious, and often relates (and misinterprets) the teachings of Christianity to even the smallest things. Lissa's family is rocked by scandal when her dad admits he is gay. She initially hates Jenna for being friends with Jake, but then after a retreat camp, they become good friends. She dropped out of Vanderbilt in the final season to pursue being a "Palos Hills Mom". She also has an on-off relationship with Jake.
Jessica Lu as Ming Huang (season 3; recurring seasons 1–2), Jenna's other best friend. She bucks Asian stereotypes because she, at first, has very little interaction with the other Asian students at Palos Hills, much to their confusion and derision. She's also demonstrated to have average at best grades. At first displaying more of a hipster, tomboy style (frequently accompanied by hats and beanies), Ming adopts a radical makeover in season 3 once she takes control of the "Asian Mafia", wearing her hair in blonde curls. She dates Fred Wu, ex-boyfriend of her nemesis Becca, but leaves before season 4 to attend a boarding school so she could apply for a decent college.
