Clean-cut high-schooler Olive Penderghast does not want to spend the weekend camping with her best friend Rhiannon and her family, so she explains that she has a date (with "George") and explains that he is a friend of her brother at college. Afterwards, when Rhiannon presses her for details, she is overheard insinuating that she lost her virginity over the weekend.Rumors begin to spread and, after she spends an afternoon in detention with her gay friend Brandon, she agrees to pretend to have sex with him to help convince the school he is straight. Several boys learn what she has done and beg her to perform the same service for them, hoping to benefit from their "lost virginities". This eventually turns into a full-fledged business, lucrative for Olive and socially beneficial for the boys, but her new reputation as tramp/slut/skank/etc. gets her the attention of the local Christian club. They want to "save" Olive, but also feel that it is vitally important to get her the hell out of the school first.Olive's life begins to resemble that of Hester Prynne in Nathaniel Hawthorne's The Scarlet Letter. Olive then decides to use the rumors to her own advantage, affixing a red A to her clothing in reference to the embattled heroine of the novel. However, the glamour and mystery quickly deteriorates, and Olive must figure out how to reclaim her good reputation.
Contains examples of:
Activist Fundamentalist Antics: Marianne's group is shown doing this. First against the basketball team, then against Olive. To the point of picketing fellow students with hateful slogans, Westboro Baptist Church-style.
Adorkable: Olive during her date at the Lobster Shack.
After School Cleaning Duty: Olive and Brandon reconnect after a period of not talking when they are both performing detention clean-up.
Almost Kiss: Olive and Woodchuck Todd when they were in eighth grade. Woodchuck Todd chickened out, and later shared his first kiss with Rhiannon.
Alpha Bitch: Marianne Bryant. First exaggerated, then lampshaded (at one point, she holds a meeting in a place called Libbey Park), then deconstructed.
And Starring: Emma Stone is credited last in the opening titles despite being the lead. She is first in the end credits though.
A Man Is Not a Virgin: Played with; although no actual sex is had, Olive starts trading on her reputation to allow guys to pretend they had sex with her in order to boost their standing around school.
Because Destiny Says So: Parodied. How does Marianne account for the fact that her boyfriend has been held back in senior year not once, but thrice? "It's His choice! If God had wanted him to graduate, He would have given him the right [test] answers!"
Big Breasts, Big Deal: Rhiannon, who is very proud to learn that she is referred to as "Big Tits" when Olive is listing her personal identifiers.
Big "YES!": During the fake sex scene in the party.
Bilingual Bonus: Olive sees Der Scharlachrote Buchstabe at the "stupid foreign movie theatre". This is the 1973 German adaptation of The Scarlet Letter. Ironically, this was lost on viewers of the German dub, since it looked just like someone photoshopped the translation in.
Olive: "Ironically we were studying "The Scarlet Letter". Isn't it always the way? The book you read in class always seems to have strong connection with whatever angsty adolescence trauma is going on. Except for Huckleberry Finn, 'cause I don't know any teenage boy who ran away with big hulking black guy"
Girl: "Oh my god. Did you hear that Brandon ran away from home? Yeah, totally; he left his parents a note that said "I'm gay, bitches" and then he skipped town with some big hulking black guy!"
At the end, almost every major character in the film is shown on a computer, watching Olive's confessional webcast. In this sequence, we also see Brandon and the aforementioned black guy watching the film adaptation of Huckleberry Finn.
Also, Olive and Mr. Griffith talk about "The Scarlet Letter," and how most students only watch the movie, and talk about how hot Demi Moore is. At the end of the movie, one student is watching the webcast, and when he realizes that Olive is not going to do anything risque, he states that Demi Moore at least got to take her top off.
During part of the narration, Olive makes fun of Demi Moore's British accent in The Scarlet Letter film by briefly putting on a Cockney accent.
Olive does an imitation of a Southern Belle's accent when her mother jokingly tells her that Brandon has come to ask for her hand in marriage.
Cant Get Away With Nuthin: Olive is a straight-A student who has never been in trouble before, but when she gets sent to the principal for nothing more serious than using a bad word (and not even that bad a word), he threatens to expel her if she is ever in trouble again.
Chekhov's Skill: During the "Pocket Full Of Sunshine" montage, Olive is seen sewing. She later uses this skill to sluttify her wardrobe.
Cluster S Bomb: Mrs. Griffith's breakdown when she decides to confess that she has been sleeping with a student, and that she has given him an STD.
Comically Missing the Point: Some of the people watching Olive's webcast do not seem to understand, even at the end, that she is not going to be taking off her clothes.
Comically Small Bribe: Olive is usually paid for pretending to have sex with people in gift cards from various stores. The lowest price she ever accepts is soon-to-expire vouchers for the foreign language arthouse cinema, with a close second being a 20% Off gift certificate.
Confessional: Olive attempts to confess and seek advice from a priest, but the other half of the confessional is empty. "Shoulda seen that one coming."
Dawson Casting: All the high school kids, to the point that the joke about Micah being several years older than the others does not work since they all look the same age. Made more jarring since they managed to get actual 14-year-olds for the flashback sequence, making it look like the characters aged 10 years from 8th to 12th grade.
"I hope you don't mind, but we had a few pre-cocktail party cocktails... like before the cocktail party. With cocktails."
"Brandon was just in the middle of telling me this really funny thing, which was really funny."
Disturbed Doves: Parodied. When Marianne finds out that Micah has chlamydia, she screams. A video playing in the foreground shows doves taking off at that same moment.
Triple Entendre: The title itself refers to a school course with a reputation for being easy to do well in, to Olive's reputation for being sexually easy, and to how easily the actually virginal Olive gets a reputation for promiscuity.
As well as the letter she pins on herself - an "A", a sign of being "easy."
Double Standard: Examined; while the guys who pretend to have sex with Olive get a reputation boost, Olive herself starts to be pilloried as a slut.
Ear Worm: In-Universe example: "Pocketful of Sunshine," by Natasha Bedingfield. Olive's grandmother sends her a birthday card that plays this song, which Olive initally says she hates. Its earworming becomes a Running Gag through the movie.
Easter Egg: If you look hard enough, you'll be able to notice that an orange is placed somewhere in every scene.
Edible Theme Naming: Everyone in the Penderghast family is named after food. Olive, her mother Rosemary, her father Dill and brother Chip.
Also, her older brother is named Kale.
Ethical Slut: Olive is a partial Deconstruction. She's not a slut herself but she has such a liberal view of sexual mores that she considers telling a friend that his wife is cheating on him to be a betraying him by destroying his marriage but is unwilling to judge a High school counselor for cheating on her husband with one of her students. It's only a partial deconstruction because, while it is shown that Olive suffers when her ideals make contact with the rest of society, she's still portrayed as mostly correct and it's society that's wrong.
The 1995 Demi Moore version. Both Olive and Mr. Griffith comment upon the mediocrity of this adaptation, and reflect that most of the students watched this film instead of reading the book or seeing the original.
Der Scharlachrote Buchstabe, the film showing at the foreign cinema Olive attends, is a 1973 German adaptation.
Gainax Ending: In universe- The characters think that the webcast is a buildup to her taking her clothes off (that's the case with at least one of the characters), but when Olive gives An Aesop and goes away to meet Todd, some of them get pretty angry.
Genre Savvy: Olive, who regularly references other teen high school movies (and how things don't seem to be going quite the same way).
The Ghost: Olive's older brother, who is mentioned in passing as how she met her so-called hook-up.
Girl on Girl Is Hot: Invoked by Olive in her big musical number wherein she kisses Rhiannon on the cheek and lays her feather boa around Rhiannon's neck; she then gives one of the female dancers a playful smack on the derriere.
Going Commando: When Olive fakes sex with Brandon, she gives him her panties and presumably spends the rest of the party in her short dress without any.
Happily Adopted: Olive's brother Chip, who is black, meaning it has never been much of a secret. The film makes fun of Oblivious Adoption when Chip remarks that "I'm adopted" and Dill, the dad, exclaims "What! Who told you?!"
Head Butt Of Love: During Olive and Brandon's "sex scene." Although completely platonic considering one of them was gay it still was a pretty adorable moment.
Jerkass: Every guy who pretends to have slept with Olive, except for Brandon, and he skips town before she can ask the favor she needs of him. Rhiannon also turns into one. — seems more like she was one the whole time, it's just the changes in her relationship with Olive framed her behavior to be more unacceptable to the audience
Mrs. Griffith might be considered this after not only subverting her Reasonable Authority Figure first impression, but then reneging on her offer to come clean, blaming Olive for helping her in the first place, and threatening to use her authority to convince everyone to accept her lies over Olive's honesty if Olive tried to reclaim her reputation. Some have said "pure evil".
Jerkass Has a Point: Rhiannon, despite her nastiness, does bring up fair talking points against Olive, such as the one about "not mistaking popularity for infamy."
Kids Are Cruel: A key theme, though there are plenty of exceptions in the cast.
Knight in Sour Armor: Olive is definitely this. For all her snarkiness, she gets into this mess in the first place because she was defending Brandon from bullying. When she agrees to take the blame for Micah's catching chlamydia, it is to prevent the break-up of Mr. and Mrs. Griffith's marriage.
Lovable Alpha Bitch: Melody Bostik, - who according to Olive, "is the most popular girl at school, because she's really pretty and has perfect hair" - actually seems to be decently friendly.
Marshmallow Hell: During the flashback with Rhiannon's parents, Olive gets a face-full of hippie boob. She was not amused.
Mascot: Woodchuck Todd, formerly known as Blue Devil Todd (the school mascot was changed after protests from the Christian group, who claimed the mascot depicted their school as devil worshipers).
Meaningful Name : Not only is Olive an anagram of "I Love", her whole name is an anagram of "I Love Pretend Shag".
Men Are the Expendable Gender: Olive is threatened with expulsion for cussing, while Brandon, who she sees leaving the Principle's office before she enters it, and who has a bloody nose as the implied result of a fight, is merely told to "sort it out". If you're a boy, nobody cares.
Never Trust a Trailer: The trailer never mentions Olive's lie about losing her virginity with a college boy, making it seem like the whole thing starts with her fake hookup with Brandon. It also shows some scenes out of order, giving the impression that Olive starts wearing the red A after she starts up her "business," instead of the other way around, even digitally removing the A in some scenes.
The movie channel trailers are even less trustworthy, eliminating the fake aspect completely and making it look like it's the story of a hot high school girl actually turning into a total slut.
New Age Retro Hippie: Rhiannon's parents. Olive says that they're weird even by California standards, and that they are the reason why she did not go on the camping trip with Rhiannon. In a brief flashback to the last time she hung out with them, the mom is shown with Godiva Hair, and the dad is offering Olive a bong hit.
Nice Guy: Todd and Brandon seem to be Olive's two real constant friends throughout the film.
Odd Friendship: Olive and Marianne become BFF for one day after Olive comforts her about her boyfriend's parents' divorce.
"And if there's one thing worse than Chlamydia, it's Florida."
Precision T Strike: Olive delivers one of these to Nina (one of Marianne's friends), in retaliation to an insult. Naturally, it gets her sent to the principal's office.
Marianne, who usually goes out of her way to avoid swearing ("no, you insensitive rhymes-with-witch!"), screams "THAT BITCH!" at the top of her lungs when her boyfriend claims Olive gave him Chlamydia.
Every computer is a Sony, and every mobile phone is a Sony-Ericsson. The reason for it being Sony specifically (other than computers and mobile phones being used in the film of course) is because Screen Gems is a Sony company.
Really Gets Around: Olive unjustly gets this reputation. Her mom embodied this trope in her youth.
Reasonable Authority Figure: Played straight with Mr. Griffith, averted with Principal Gibbons, and subverted with Mrs. Griffith, who seems like a reasonable and empathetic guidance counselor, but then refuses to actually listen to Olive just when Olive is offering to open up to her, and instead assumes that the rumors about Olive are true, even though her husband had already told her they weren't. And that's before she's revealed to be pure evil.
Transparent Closet: Although Brandon is fairly Straight Gay, he just seems to get picked up by everyone's Gaydar. Unfortunately, that leads to him getting bullied and the homophobic principle refusing to do anything about it.
Troubled Sympathetic Bigot: Marianne's seem to suffer worse from her own actions then it hurts Olive, and it's not from some kind of retributive Karma either. She seem to mean well, but be horribly misguided.
Two-Person Pool Party: Referenced. Melody Bostic's parents let her have a party ever time she catches them having sex in the pool which, according to Olive, is about once a week.
Was Actually Friendly: Marianne really hated Olive. But when Olive showed her a bit of kindness and support, she quickly changed her attitude and wanted to be friends instead. It didn't last long, but that's for entirely different reasons. Marianne's boyfriend cheated on her and got a venereal disease, then lied and pretended he got it from Olive.
Waxing Lyrical: Olive still has the "Pocketful Of Sunshine" Earworm mentioned earlier, so when talking about her fictitious weekend with "George" she ends up mentioning that she feels like "I got a love, and I know that it's all mine".
Well-Intentioned Extremist: It really seems like the Cross Your Heart Club is trying to help Olive, at least until word gets out that she banged Micah; then it was more of a grudge match.
The movie was initially written as a hard-R adult comedy which featured, according to the writer Bert Royal, 47 F-bombs. This gives a little more credence to Olive's response to Nina, knowing that "twat" was probably originally a case of Country Matters — it would certainly make the principal's reaction a bit more justified.
Emma Stone's audition, included as a special feature on the DVD and Blu-Ray releases, reveals that the original script had Brandon as the source of Olive's middle-school crush, and he was the boy that she lied about kissing during "Seven Minutes of Heaven."
What the Hell, Hero?: Rhiannon was the first to call Olive out on her growing reputation, though Olive shoots her down by saying she's just jealous of her new "popularity".
Mrs. Griffith is Rev. Dimmesdale who pretends to be a pillar of moral character,
Olive is Hester in that she is unjustly accused of being a whore.
Olive is also Hester's husband Chillingworth when she exposes Mrs. Griffith's infidelities but comes to regret it.
Wild Teen Party: Melody Bostic's. Subverted; all references to sexual activities at her parties involve Olive, and both involve her lying about what happened (Olive and Todd lie about kissing in eighth grade, and Brandon and Olive are not actually having sex in the spare bedroom now).