<P> On New Years, Matty, Jenna, Jake and Tamara get together and decide to crash Sadie's aunt's party . While there, Matty reconciles with his mother and Jenna finds a new guy to kiss at midnight, a guy she later finds out is a sophomore . Meanwhile, college acceptances are rolling in and it seems as though everyone's been accepted except Jenna . Jenna attempts to get into Lockard University, but while she doesn't get accepted, her mother does . On Matty's 18th birthday, Jenna competes with his new girlfriend Gabby, only to realize Gabby is genuinely nice and means no harm . Jenna confesses to Matty that she feels like Gabby's virginity is worth waiting for, and that her own wasn't . Matty argues and tells her that he didn't want to be alone when he opened a letter which would tell him who his birth parents are, which showed how much Jenna means to him . After Matty's disappointment of discovering that his birth mother does not want to be found, Jenna comforts him and the two end up kissing . Jenna tells him she can't because he needs to be loyal to Gabby but Matty says, "It's us . It's kinda different, goes a bit beyond the rules of high school ." During spring break, Jenna locates Matty's father and they plan to meet him in Mexico . Gabby shows up and goes with Matty instead . While in Mexico, Tamara gets engaged to a man named Adam whom she meets in a bar . Adam is in basic military training and she accepts his proposal, thinking that he is going to serve somewhere far away but in reality, he will be in California . Meanwhile, Mrs. Hamilton discovers she is pregnant and considers not going to college . Later, it is revealed that Gabby slept with Jake and Jenna finally lets go of Matty as she begins dating a friend of Adam . Matty goes to the beach to get away from things but instead sees Jenna and her new date in the distance . Jake then shows up on the beach, initially wanting to confess about him and Gabby but decides to keep quiet instead . The season ends with Matty staring at Jenna in the distance on the beach, wondering whether he has lost his chance of true love . </P> <P> In season 5A, Jenna and Matty have a bumpy ride as Jenna finds out that she does really love him but doesn't know how to tell him . Tamara breaks up with Adam after Jenna told everyone the truth about the fake engagement during the engagement party . Jenna decides to go to Wykcoff whilst Matty goes to Berkeley on a soccer scholarship and Sadie and Tamara go to New York . The mid-season ends when Matty confesses his love to Jenna at the Senior prom and they get back together . On graduation day, Matty tells Jenna that his soccer practice starts the day after their graduation and he had to leave straight away . Devastated that they are going to be on different sides of the country, Jenna decides to spend the summer with Matty at Berkeley . Season 5A ends with Jenna and Matty arriving at Berkeley . </P> <P> In Season 5B, Jenna arrives home after her first year of college alongside Tamara, Sadie, Matty and Lissa . Jenna is shocked to find that over college, Sadie and Tamara have become really close and she believes Tamara has forgotten her slightly . Lissa left college to become a' Palos Hills Mom' as it has always been her dream . Jake had taken a gap year so was working as manager at the country club . However, Jenna and Matty had split over the year and no one knew why until she told the story . When Matty visited her during Halloween, he decided to transfer to Wyckoff to be closer to Jenna and because he didn't enjoy Berkeley . However, Jenna doesn't want him to transfer just because of her so Matty storms out, upset, and they had broken up and hadn't spoken till this summer . Jenna got a summer internship at Idea Bin, an online writing company, where she rekindled her romance with Luke, who got her the internship . Lacey and Kevin had a baby who cries every time Jenna is near, as she has been away for a whole year . Tamara gets into huge debt and so Jake hooks them all up with jobs at the country club . Tamara meets a rich man called Patrick who soon becomes her boyfriend . Lissa's mom gets engaged to a rich man who works for a toilet hygiene firm and decides she no longer wants to be a Palos Hills Mom . Instead she starts' Atonercise' lessons which become very popular as she starts building her own business . Jenna meets Matty's girlfriend Sully who is a party girl . She tells Jenna how a girl, not knowing that it was Jenna at the time, had screwed Matty over and made him depressed . Matty and Lacey go to the same German summer school and become partners, therefore Jenna always sees him around the house when he and her mother are working together . Jenna decides to transfer to SCU to be closer to Luke even though she enjoys Wyckoff . At the end of the summer, Camp Pookah was closing for good and they all decide to go to their last day . There, Matty takes Jenna to the closet where they first had sex 3 years ago and Jenna talked about how Matty knew nothing about her then but know he knows her better than anyone . Matty tells Jenna that he still loves her but that she choose herself first and that she shouldn't and doesn't need to transfer to SCU . Throughout his talk, Matty twirls a ring made by one of the children in his fingers, supposedly for Jenna . They end up kissing and getting back together and the season ends with everyone including Val, her parents, Ally and all her friends, including Matty, sitting round the campfire, having fun . </P> <Ul> <Li> 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 . </Li> <Li> 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 . </Li> <Li> 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 . </Li> <Li> 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 . </Li> <Li> 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 bossy 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 . </Li> <Li> Molly Tarlov as Sadie Saxton, one of the most popular girls in school, though mostly because everyone fears her . She is head cheerleader despite being overweight at the beginning of the series . 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, who likes her despite how cruel she can be . </Li> <Li> Desi Lydic as Valerie Marks (seasons 1--5A; appeared in the 5B finale only), 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 ." </Li> <Li> 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 . 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 also has an on - off relationship with Jake . </Li> <Li> 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 . </Li> </Ul>

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