Cast: Emma Stone, Aly Michalka, Amanda Bynes, Penn Badgley, Thomas Haden Church, Patricia Clarkson, Stanley Tucci, Lisa Kudrow, Cam Gigandet, Malcolm Mcdowell, Dan Byrd, Jake Sandvig, Fred Armisen, Juliette Goglia, Lalaine, Stacey Travis, Matthew Timmons, Bonnie Burroughs, Rawson Thurber
Plot / Synopsis:
Olive Penderghast (Emma Stone) lies to her best friend Rhiannon (Alyson Michalka) about going on a date in order to get out of camping with her and her hippie parents. Instead, she hangs around the house all weekend, listening to "Pocketful of Sunshine". The following Monday, pressed by Rhiannon, Olive lies about losing her virginity to a college guy. Marianne (Amanda Bynes), a girl at their school who is a zealous Christian, overhears her telling the lie and soon it spreads like wildfire.
The school has a conservative church group run by Marianne who decides Olive will be their next project. The group's harassment, disguised as concern, comes to head at an English class taught by Mr. Griffith (Thomas Haden Church). The class is reading The Scarlet Letter, a novel about adultery and shame. When one of the girls from the church group makes a snide comment to Olive suggesting Olive wear a red A as well, Olive shoots back and Mr. Griffith sends her to the principal's office. During her detention she tells her friend Brandon (Dan Byrd) the truth, and he explains how others bully him because he's gay.
Brandon comes over later and asks Olive to pretend to sleep with him so that he will be accepted by everyone else at school. Brandon convinces Olive and they pretend to have sex at a party. Afterwards she bumps into Todd (Penn Badgley), whom she almost kissed years ago during seven minutes in heaven but instead agreed to lie about it when he said he was not ready.
After having a fight with Rhiannon over Olive's new identity as a "dirty skank", Olive decides to counteract the harassment by embracing her new image as the school tramp. She begins to wear more provocative clothing and stitches a red 'A' (a la Hester Prynne in The Scarlet Letter) to everything she wears. Boys who usually have had no luck with girls in the past begin to give her gift cards and money to say they have had sex with her in order to increase their own popularity, which in turn increases her reputation.
Olive comes to short-lived understanding with Marianne, but it is ruined when Marianne's boyfriend Micah gets chlamydia and lies that Olive gave it to him. Olive sees Mrs. Griffith, the guidance counselor and her teacher's wife, who tearfully confesses that she slept with Micah. Olive promises to take the blame to save Mrs. Griffith's job and marriage. Rhiannon, partly jealous of the attention Olive is getting, joins the church group and starts harassing her former best friend.
Olive soon realizes that, though everyone thinks she is sleeping around, no one was actually attempting to sleep with her. This changes when Anson comes up to her and asks her out. The date goes sour when Olive sees Rhiannon at the restaurant and remembers she has a crush on Anson. In the parking lot, Anson attempts to pay her off; Olive asks what they will say happened but Anson thinks he will actually get sex and tries to kiss her. She resists and he drives off. Todd, who works at the restaurant, sees her and offers to drive her home.
Todd tells her that he does not believe the rumor mill, he remembers when she lied for him because he wasn't ready for his first kiss and thinks she is actually great. He says he wishes she actually was his first kiss, and not Rhi. Todd then asks for permission to kiss Olive but she says no, wanting to wait until she sorts out her life.
Olive goes to the boys that propositioned her and demands they admit that the rumors are all lies but they refuse (and Brandon even ran off, leaving behind a note telling his parents he's gay). When she goes to Mrs. Griffith to make her come clean, she refuses and implies that no one would believe Olive over her. Olive runs to Mr. Griffith and tells him the truth but immediately regrets it, realizing she just destroyed a marriage.
To get everything finally in the open, she does a song and dance number at a pep rally and pretends she will be doing a sex show via web cam with Todd. In actuality she confesses what she has done. She also makes up with Rhi, apologizing for lying. When she is finishing up, Todd comes by riding a lawnmower, holding a boombox and tells her to come out. She closes her web cam confession saying she really likes Todd and maybe she will lose her virginity to him in the future but at the end of the day it is no one's business but her own. She leaves the house to kiss him and they ride off from the neighborhood on the lawnmower.