1985. There’s a huge high school dance at the brand new Arden Mall (Like You Like It)!
Straight-A senior Rosalind Duke wants to go with varsity wrestler Orlando Bateman, but she is too shy to face him. Worse, snotty Audrey Shepherd has been dating Orlando for a whole month.
Rosalind’s cousin and best friend Celia Duke discovers that Audrey and Orlando are on the outs, so she encourages Rosalind to make a move (Be A Little Wild).
Though Audrey and the entire school adulate Orlando, he laments they don’t see that beneath his popular exterior, he misses his late parents and yearns for someone to truly understand him (Orlando).
Rosalind and Orlando finally say hello to each other between classes (It Could Totally Happen), but they are unjustly suspended from school thanks to Audrey’s machinations and the treachery of Oliver Bateman, Orlando’s jealous older brother and the 19-year old truancy officer of the school.
With Rosalind’s hopes dashed and nowhere to go, she and Celia decide to flee to the Arden Mall. Audrey, whose father owns the mall, threatens the girls that if they are discovered at Arden, they will be arrested. So Rosalind and Celia decide to go in disguise: Rosalind as a frat dude named “Corey” and Celia as a Madonna wannabe dubbed “Ladonna” by their ride: Walter “Touchtone” James, a randy junior who pines for Celia. They escape to the mall (Gotta Get Out).
At the mall, Sylvie Feldman and Phil Lipschitz, workstudy students at the food court, meet bitter rocker Jackie West, whose band is playing later at the dance. Jackie discourages them from ever falling in love. Sylvie, though, yearns for Phil, who ignores her hints. When “Corey” comes across Sylvie, “he” instructs her to take a risk and stop hinting. Sylvie makes her move, but Phil makes it heartbreakingly clear: they are only friends. (Sylvie’s Question/ Phil’s Answer).
Orlando has also escaped to the mall. When he encounters bitter Jackie, he asks to hold her guitar. His late father had the same kind of guitar, but Oliver sold it. Orlando proclaims that he wants to write a song to a special girl he likes, but Jackie teases him that he should post poems on the wall dedicated to Rosalind. He takes her seriously.
Rosalind, Celia and Touchtone discover some of the poems. Celia recognizes Orlando’s handwriting, to Rosalind’s elation. The three split up to look for Orlando, but Rosalind laments she is stuck in disguise as a guy. She decides to use that to her advantage and become “buddies” with Orlando (Be A Little Wild Reprise 1).
Celia and Touchtone come across each other in a remote area of the mall. After his repeated attempts to woo her, he gives up. She inadvertently admits she is interested in him, but tries to deny it. Still, there’s something in the air, so she gives in. The two of them share a first kiss, which ends in disappointment for both of them (Blame It On The Mall).
“Corey” finds Orlando and earns his trust. Orlando admits that for three years, he’s been too shy to talk to Rosalind (Easy Way Out). “Corey” hatches yet another plan: “He” will act like Rosalind to tutor Orlando about wooing her.
They are interrupted by Sylvie, who blames “Corey” for Phil’s rejection. After Orlando and “Corey” decide to meet up later, “he” confronts Phil. Phil falls for “him” (Phil’s Realization). “Corey” goes off to meet up with Orlando while Sylvie informs Phil she wants to go to the dance with “Corey,” not Phil.
Celia, crushed and confused by her encounter with Touchtone, locates Rosalind and begs to leave the mall. Rosalind wants to stay so she can continue her ruse with Orlando. When Celia accuses Rosalind of lying and hiding behind her disguise, Rosalind accuses Celia of caring about boys only if they are into her. They angrily separate as Orlando enters.
Rosalind lashes out at Orlando for being late and never really getting to know her, when she realizes she is still in disguise as “Corey.” Orlando assumes “Corey” is playing a fiery Rosalind, and likes it. The two bond further when Orlando opens up to “Corey” about his parents. “Corey” asks Orlando if he truly knows what Rosalind is like, and his description moves her to come clean about her disguise. But as she is about to reveal the truth…
Audrey arrives and wants an explanation about Orlando’s poems. Orlando admits he wants to take a chance on Rosalind. Furious, Audrey threatens to cancel the dance, then falls for “Corey,” claiming “him” as her new date for the dance. “Corey” claims “he” already has a date points to the only other girl in sight: Sylvie. Rosalind steps out of the action to convince herself that the actions she is about to take are “really not that complicated” (Complicated). Phil is devastated “Corey” likes Sylvie, but Sylvie is thrilled “Corey” picked up on her plan to make Phil jealous.
“Corey” promises Audrey a date with “his” frat bro. After Audrey exits, “Corey” confides to Orlando that “he” will simply stand up Audrey. Orlando calls that out as a jerk move, so “Corey” promises to take Audrey. As Orlando exits, Rosalind considers her double-date predicament, with a “Dream Celia” chiding her. Rosalind doubles her commitment to her goal to get Orlando as Act One ends… but not before Oliver enters, searching for the truant students.
Celia, eager to leave the mall, is shocked when Oliver approaches her on his quest to find the students. Since she is in disguise as “Ladonna,” he does not recognize her but admits he likes a girl named Celia. He begs “Ladonna” to help him out by transforming him into a guy that Celia would notice. During a makeover montage, Oliver falls in love with “Ladonna,” and Celia finds herself falling, too. But she’s afraid of telling him who she really is (Creating A Monster).
Rosalind, desperate to get out of her double-date “sitch,” begs Touchtone to take Audrey to the dance. He refuses: he never again wants to feel that sting of disappointment he felt with Celia. Frustrated, Rosalind leaves. Audrey, looking for Corey, passes by Touchtone and mistakes him as Corey’s “frat bro.” She laughs — she needs a real man like Corey. Touchtone laughs at her for thinking Corey would like her. She runs off, upset to her core that he is being mean to her. He realizes that he has hurt her feelings — moreso that girls actually have feelings — and swears he’ll protect her from Rosalind’s deception (Blame It On The Mall Reprise).
Sylvie admits to Phil that she was just using Corey to make Phil jealous, and that Corey is not into her. Phil admits he really likes Corey — and boys in general. Sylvie’s adverse reaction to the news causes a rift in their friendship (Sylvie’s Reaction).
Still distraught, Audrey crosses paths with “Corey.” She wails to “him” about how tough her privileged life is (I Wanna Know Why). Rosalind, now feeling responsible for hurting Audrey, decides to take Audrey to the dance after all (Be A Little Wild Reprise 2).
At the dance: Jackie West sings her hit song (So Close So Far Away) as the backdrop for an action-filled contest:
“Corey” shows up for Audrey, then disappears and reappears as Rosalind for Orlando. But her constant back-and-forth makes Orlando doubt if Rosalind truly wants to be with him.
Sylvie discovers “Corey” is a girl and dances with Phil to divert him from the truth.
Touchtone tries to tell Audrey about “Corey” but doesn’t want to hurt her or Rosalind.
Thanks to his transformation, Oliver makes amends with Orlando and tells him he bought back their Dad’s guitar, which is waiting for Orlando at the mall’s music store.
“Ladonna” tries to admit who she is to Oliver, but is too afraid of revealing herself as Celia, so she begs Rosalind to stay in disguise as “Corey.”
With no Rosalind in sight, Orlando leaves, while “Corey” and Audrey dance their way into winning the contest.
Orlando reappears and takes the stage to sing a song for Rosalind, hoping she will show up (Be With Me). So moved by the song, “Corey” kisses Orlando — forcing Rosalind to finally reveal herself. When Audrey goes in for the kill, Celia leaps to protect — and reveals herself as Celia. When Audrey realizes that Touchtone was protecting her and truly cares for her, she goes off with him. Phil thanks Sylvie for doing the same, reaffirming their friendship. Rosalind and Celia each face their respective suitors. Oliver softens toward Celia, but Orlando storms off.
At school the following Monday, Rosalind approaches Orlando. She admits they never would have worked out as a couple but did work when she was “Corey” because they both had the courage to talk to each other. She bares her soul to him, affirming that as long as they are true to themselves, they have a chance. He relents and affirms his feelings for her. As they embrace, the other couples affirm their love for each other, and that it all works out Like You Like It (Finale).