In voiceover, Cher relishes how effective her good deed has been, and as the camera shifts to show an intoxicated boy throwing up into the pool, Cher says, “Love was everywhere, and even though I was alone, I was really happy for Tai.” Suddenly, her phone rings, and she answers to hear her father, who scolds her for being out so late. She lies that she is grabbing a snack with her girlfriends, and he tells her he wants her to be home in 20 minutes. When she tells him that it might take longer, he says, “Everywhere in LA takes 20 minutes,” and the shot shifts to show a partygoer passed out on the steps of the party. Cher, Elton, and Tai walk out of the party and Cher greets Summer, who offers Cher a ride home. While Elton insists that he will drive Cher, Tai realizes that Summer is also going in the direction of her house and goes to get in Summer’s car. Elton is pleased and says that Tai can go with Summer and he will drive Cher, but that does not fit with Cher’s matchmaking plans, and she tries to pass Tai over to Elton. Cher and Elton pass Tai back and forth, until Elton insists that Cher come with him, and helps her into his car. Cher is upset. Smiling, with a light-up snowman in her lap, Tai waves to an annoyed Cher. The cars leave.
As they make their way down the street, Cher tries to direct the conversation towards how good Tai looked, but Elton sings “Away” by the Cranberries, and barely responds. Cher continues to extol Tai’s beauty, but Elton looks at her seductively and tells her that she’s one of his best friends, “and I do not have friends that are girls.” Cher smiles and tells Elton that she wants him to be happy, having seen how hard his breakup was. When Elton tells her that he thinks they both know what it feels like to be lonely, Cher is momentarily confused, but continues in her campaign to set him up with Tai. Unexpectedly, Elton turns the car into the parking lot of a gas station, declaring “I knew it!” Cher is confused, as Elton unclips his seatbelt and leans over to kiss her. Disgusted, Cher tries to clarify, “Don’t you mean Tai? You have her picture in her locker,” but he tells her that he put up that picture because Cher was the photographer.
Elton leans over and tries to kiss her again, but she pushes him away, and he laughs. When he tries yet again, she pushes him away once and for all, which causes him to throw up his hands defensively. Elton accuses Cher of having flirted with him all year, and when Cher insists that she was only trying to set him up with Tai, he is shocked: “Why would I go with Tai?” After Cher presses him why he wouldn’t go with Tai, he says, “Don’t you even know who my father is?” which prompts Cher to call him a “snob and a half.” Elton then tries to reason once again with Cher, insisting that they “make sense” in a way that he and Tai do not. When he tries to kiss her again, Cher pushes him away and gets out of the car angrily.
Huffing and puffing, Cher begins to walk away in her mini dress and heels. When Elton tries to coax her back into the car, she squeals, “Leave me alone!” and he drives away angrily. “Hey, where are you going?” she calls to him, suddenly feeling desperate. She takes out her cellphone and calls the operator looking for a cab company. As she argues with the operator, we see a hand point a gun to Cher’s head. A man is mugging her, and tells her to hand over the phone, which she does, whimpering. He asks for the bag too, which she reluctantly hands over. When he tells her to lie down on the ground, face down, she hesitates, insisting that her dress is an Alaia. “It’s like a totally important designer,” she scoffs, when her mugger doesn’t recognize the name, but he tells her he will shoot her in the head if she doesn’t lie on the ground. Weeping, she lies on the ground and he tells her to count to 100, and the mugger runs away.
Cher gets up, and in voiceover, she troubleshoots about how to get home after her horrible night—“sexually harassed, robbed….” Walking slowly up to a payphone, Cher decides finally that she has to call Josh, whom she interrupts lying on a bed with a girl. As Cher gets more and more upset, Josh finally asks her where she is, and when she tells him “Sun Valley,” he says “Man, you owe me,” and hangs up the phone. The shot shifts to Cher in the back of Josh’s car, as Josh and his intellectual date, wearing a beret no less, argue about a shared professor. Cher smirks from the backseat as the date uses terms like “the garden of ideas” and quotes Hamlet—“to thine own self be true.” When the date misattributes the Hamlet quote to Hamlet himself, Cher recalls the Mel Gibson adaptation of Hamlet and corrects her: “That Polonius guy said that.” Josh laughs, charmed by Cher’s accurate correction. As they arrive at the date’s house, Josh tells Cher that he is going to walk her to the door. Cher stays in the car and watches the couple go up to the door and make out, which visibly dismays her.
As Cher receives a massage, she wonders, in voiceover, how she will tell Tai that Elton doesn’t like her. The scene abruptly cuts to Tai tearfully sitting on a bench in the locker room, asking if it’s “her hips” that made her unattractive to Elton. Cher and Dionne try to comfort her, telling her that she’s too good for him. “If I’m too good for him, then how come I’m not with him?” Tai sobs. Cher is struck with an idea—they’ll go to the mall, “have a calorie fest,” and see the new Christian Slater movie. Tai is grateful, and the three friends hug. Later, at a restaurant, Dionne and Tai admire a waiter and the girls laugh. The girls then discuss what kinds of body types they like in a guy, and Tai reveals that she “doesn’t really care either way…Just as long as his you-know-what isn’t crooked.” Dionne shushes Tai and tells her not to scare Cher, and tells Tai that Cher is a virgin. Tai is shocked to learn this, and Cher explains that she is not interested in sleeping with someone who isn’t the right person. Cher then throws her bread at Tai, revealing that Dionne too is “technically a virgin,” implying that she and Murray have not had penetrative sex. Tai becomes suddenly upset, and when Cher asks why, Tai reveals that it is because “Rollin’ with the Homies” is playing at the restaurant, which she considers her and Elton’s song. Tearfully, Tai does the goofy dance move that she and Elton shared at the party the previous evening, and Cher and Dionne comfort her. Tai cries and bangs her head on the table, as Cher considers how to help Tai in voiceover. “I could tell Tai’s grieving period would be considerable,” she thinks, frowning, “Unless I found someone to take Elton’s place right away.”
The scene shifts to show the low slung jeans of a boy, his underwear hanging out. We then see a group of boys in clothes emblematic of the 90s—baggy pants, tie dye, backwards hats, chains and skateboards—walking down the sidewalk at the school as Cher bemoans the current male fashion trends. “We’re expected to swoon? I don’t think so!” she says, as the boys walk triumphantly to the song “All the Young Dudes.” Spacing out in class, Cher holds a pink pen with a fluffy base and continues to lament how difficult it is to find a desirable high school guy to date. Her daydreaming is interrupted by the entrance of a suavely dressed boy, in khakis and a black t-shirt. He makes eye contact with Cher and smiles, and she is enamored.
Mr. Hall wanders over to the boy, and identifies him as “the elusive Christian.” Christian takes a seat in the class, as Cher narrates that while she knows she needs to find a guy for Tai, she finds herself unexpectedly attracted to Christian, and wants to find a guy for herself as well. She strategically pushes her pen onto the floor, hoping that Christian will pick it up for her. He does, leaning forward and putting it on her desk, saying “Nice stems.” Mr. Hall interrupts their held eye contact to invite Cher up to give her oral presentation on “Violence in the Media.” Cher comes to the front of the class and begins her presentation, yet another vapid assessment of serious events. In regards to violence in the media, Cher explains that until mankind has eradicated violence from actual current events, there ought not to be less violence in “shows that need it for entertainment value.” Christian watches her presentation admiringly, clapping appreciatively along with the class. When Mr. Hall asks if anyone would like to comment, Elton asks to go to the nurse, and Travis gives “Two very enthusiastic thumbs up!” Amber, however, is not amused, and says the presentation “reeked.” Cher fires back that the only thing that reeked was Amber’s impostor designer perfume, as the bell rings. As everyone files up, Christian comes up alongside Cher and tells her, “I dug it,” which makes her smile longingly.
We see a closeup of flowers on Cher’s desk, and she runs excitedly to open the note hidden in it. In voiceover, she says, “During the next few days I did what any normal girl would do: I sent myself love letters and flowers and candy.” We see Cher showing the flowers to a neighboring student as Christian reads Junky by William S. Burroughs behind her. He smiles at the flowers Cher received. The scene cuts to show Cher opening a box of chocolates and offering one to Murray and then Christian, who takes one. “Anything you can do to draw attention to your mouth is good,” Cher narrates, eating the chocolate seductively. We then see her on another day, wearing a tank top as she says, “Also, sometimes you have to show a little skin. This reminds guys of being naked, and then they think of sex.” Christian leans forward and asks Cher what she’s doing the next weekend. “I’m new, but I thought maybe you had an in on the heavy clambakes,” he says. She tells him that Josh’s friends are having a party, and invites him along.
We then see a number of depositions on a table, as Cher narrates that her father had to begin work suddenly on a very important case, and that Josh came to help him. Josh and Mr. Horowitz sit at the table looking at the depositions as the doorbell rings. Cher calls down that she cannot answer the door right away, and has to make Christian wait a little while before fetching him. When Mr. Horowitz refuses to do it, she implores Josh to let Christian in, and he grudgingly gets up and answers the door. Christian saunters in wearing a fedora, which Josh snatches off his head, telling him that Cher isn’t ready. Christian extends a handshake to Mr. Horowitz, who looks at him, mystified. “You drink?” Mr. Horowitz asks him. When Christian mistakes his question for an offer, Mr. Horowitz scolds him, telling him that he would never give alcohol to a teenage driver. When Christian tells him, “The protective vibe, I dig,” Mr. Horowitz mockingly asks if Christian thinks he is a member of the Rat Pack.
Cher comes down the staircase in a white minidress, and we see Josh dumbstruck at her beauty. Christian and Cher embrace, as Josh turns to Mr. Horowitz and asks, “You’re not letting her go out like that, are you?” This prompts Mr. Horowitz to call her in and interrogate her about her dress, which she tells him is Calvin Klein. When he tells her to put something over it, she laughs that she was just about to, and goes upstairs to get a layer. Mr. Horowitz threatens Christian paternalistically, saying that he has “a .45 and a shovel.” Cher collects Christian and they leave, Josh watching them go, visibly jealous.
Outside, we see Christian’s car, a vintage yellow convertible. As they get in, Christian tells Cher that her dad is pretty scary, which seems to delight her. As Cher looks at herself in the rearview mirror, Christian asks her if she likes Billie Holiday, to which she responds, “I love him,” misidentifying the famous female jazz singer. Billie Holiday plays as they drive down the street past a lavish fountain. Back at the house, Josh says, “I didn’t like him,” before adding that he might go along to the party. Mr. Horowitz tells him that he doesn’t need his help and so Josh leaves, telling Mr. Horowitz that he will watch Cher for him.
The scene shifts to the party, where the band, The Mighty Mighty Bosstones, plays an energetic ska song. Cher and Christian dance to the song jubilantly, surrounded by other party-goers. Christian is a goofy and eccentric dancer and makes Cher laugh. We see Tai enter the party from elsewhere, and wave to Cher, before clumsily falling down the stairs. Cher runs to her aid, and Tai is extremely embarrassed, as a man runs up and asks if she’s okay. Suddenly distraught, Tai sees Elton dancing with Amber, but Cher tries to assure her that they are probably only dancing. “Do you think she’s pretty?” asks Tai, but Cher scoffs and calls Amber a “full on Monet.” She defines a “Monet” as being like the work of the famous painter—fine from far away, “but up close it’s a big old mess.” Christian walks up, and when Cher asks him what he thinks of Amber, he lowers his glasses and says, “Hagsville,” which seems to comfort Tai. Christian effeminately bemoans the fact that they are charging money for beer, and Cher hands him some money. He puts it in his breast pocket and kisses her on the cheek.
When he walks away, Cher says, “Do you see how he’s falling in love with me?” We see Christian at the bar, pushing away a girl who puts her hand on his shoulder. Christian makes impassioned conversation with the bartender, and Tai points out that Josh is at the party. Josh waves to Cher, and she sarcastically waves back. Tai asks Cher for advice on how to wear her shirt, and Cher begins to help her tie it around her waist, but they are interrupted by Christian, who leads Cher onto the dance floor, slinging her arm over his shoulder. Tai watches admiringly as the Mighty Mighty Bosstones continue to play. Alone, Tai dances awkwardly, waiting for someone to ask her to dance. Cher dances jubilantly, but becomes disheartened by the sight of Tai looking lonely, flanked by two much-taller guys.
Cher’s controlling ways come to a head at the end of the party, when she is unable to see that there is no spark between Elton and Tai. As Cher and Elton pass Tai back and forth like a rag doll, trying to determine how their carpool will work out, Cher comes off as ignorantly unaware of the actual stakes: Elton has had a thing for her all along, not Tai. While Cher is very socially observant throughout, her inability to notice that Elton is interested in her reveals a large blind spot. Cher is so intent on doing what she thinks are “good deeds” for other people, that she cannot recognize when she herself is entangled in something. Cher’s blind spot not only diverts her attention from her own involvement in her schemes, but puts Tai and Elton in an uncomfortable situation. Cher thinks she is especially observant of the social world around her, when in actuality, she is just as “clueless” as everyone else.
Additionally, in this portion of the film, we are reminded of the snobbery and wealth of the teenaged characters, and the ways that Cher cannot transcend class tension with her idealistic good deeds. When asked to cite why he would not date Tai, Elton says, “Don’t you even know who my father is?” While the characters are innocent and young, they are also in thrall to their own privileged upbringing. Elton is only in high school, but he knows that the powerful occupation of his father prevents him from dating someone whose class position is lower, like Tai. Part of Cher’s blind spot is her inability to anticipate Elton’s snobbery, and her belief that he would be interested in Tai, in spite of his prejudices. This moment is meant to be satirical—a high schooler saying “Do you know who my father is?” is reprehensibly spoiled, comically so—and it highlights the superficiality of a particular wealthy Los Angeles milieu. Cher wants to try and overlook the class strictures of her community and sow the seeds of romance, but is unable to, causing a painful rather than a happy situation. Cher’s naive optimism proves ineffective in this moment.
Cher’s naivety continues to reach broadly comedic proportions when she is confronted with an angry mugger, and then again when she corrects Josh’s pretentious intellectual date. While visibly shocked and upset at being mugged, Cher remains unwilling to ruin her clothes for the sake of safety, and when the mugger asks her to lie on the ground, she mentions the name of the dress designer as though that will invoke sympathy and awe. Predictably, the mugger couldn’t care less about the designer, and forces Cher onto the ground anyway. While someone else might meet the situation in a more serious way, Cher’s passion for fashion makes her a particularly humorous victim of a mugging. She cannot even see the stakes clearly when a gun is pointed at her; she is too worried that her fancy dress will be ruined. Cher’s sense of proportion is charmingly askew; she is always paying particular attention to the superficial. Yet this serves her well when she accurately recalls that it was Polonius who says “To thine own self be true” in Hamlet. Cher has not read the play, but she can recall Mel Gibson’s movies with precision. While Josh’s date postures and performs intellectuality, Cher calls the girl’s bluff based on her own knowledge of pop culture. Cher proves herself to be a kind of savant, out-smarting the intellectual. Cher may be naive, but she is not stupid.
Cher’s innocence and naivety extends into matters of sex. When the girls go to get a meal together, Cher doesn’t understand Tai’s euphemisms for her preferences about a guy’s penis. While Cher may be the expert in social matters and status symbols, she is far behind Tai when it comes to sex. Tai is shocked to learn that Cher is a virgin, and cannot quite understand Cher’s philosophy of waiting to find the right person before having sex. It is then revealed that Dionne is also a virgin, and Tai can hardly believe that either. Cher, for all her performances of sophisticated and maturity, has not found the right person with whom to have sex, which distinguishes her from the earthier and more worldly Tai.
The first boy to pique Cher’s attention is Christian, who represents everything that the other boys in her life do not. He has a honed aesthetic sensibility, dresses elegantly, and speaks and acts in a way that hearkens back to old Hollywood and post-war glamor. He speaks in old-fashioned slang, tucks his t-shirts into his khakis, drives a vintage car, reads the beats, and listens to old jazz. Cher does not know much about him, but she knows that she thinks he has a good sense of style and he is not like other guys. A comic moment occurs when he asks if she wants to listen to Billie Holiday and Cher pretends to love Billie Holiday. The only problem is: Cher thinks Billie Holiday is a man. Christian’s allure is his mystery and his idiosyncrasies, which slowly reveal themselves to be more and more sexually ambiguous—as when he refers to Amber’s appearance as “Hagsville” and seems more emotionally available to the male bartender than to Cher.