Bobby Jonathan Silverman graduates high school with his friend Mike George Newbern, and his father pushes him to forge his own path while gifting him a book of romantic poems that are supposed to guide him toward romance. At college, the pair join a fraternity where Bobby can finally be himself and not simply follow in his dad’s footsteps; the fraternity leader, however, presses Bobby to train his pledge brothers to imitate his father, creating an early tug‑of‑war between independence and family expectations.
At a party, Bobby meets Sybil Michele Matheson and tries to charm her with the poems, but it doesn’t land. Encouraged by his own shifting perspective, he nudges Mike to abandon his dad’s rigid advice and seek a girlfriend of his own. The night soon spills into a clash of relationships when Diana [Alyssa Milano] and her boyfriend Derry clash—Derry doesn’t listen to her, they break up, and then they briefly reconcile after his apology.
As Bobby tries again to win Sybil, he stumbles into a mess of studies and identity. He lands in an all‑female sociology class about the history of women, and discovers that both he and Mike have unknowingly enrolled in a taxidermy class as well. The pledge brothers reminisce about The Brady Bunch for their leader, who then tasks them with stealing a painting from the Zeta Alpha Zeta sorority house. After four failed attempts, Bobby disguises himself as the persona of Roberta Jonathan Silverman and fools the sorority, though he still cannot secure the painting. The balancing act of being both himself and Roberta strains him: he misses fraternity activities as himself but wants to stay Roberta in order to stay close to Diana.
Bobby asks Diana for study help, but she reads his signals as a date invitation. During a thunderstorm, he fails to seduce her, and she uncovers the Roberta scheme in a pledge book. When Roberta is elected president of the pledge class, the sorority invites the persona for drinks, and Derry flirts with Roberta, which Bobby deliberately plays off as gross. Bobby and Mike devise a plan to trap Derry with Diana in a compromising moment, hoping to set things right.
The next day, Derry stumbles into the library and the notes hint at taking his clothes off; seeing this, Diana ends their relationship. Bobby learns more about girls and, as Roberta, tries to win Diana over again, but when he reverts to his real self and shares a kiss, she slaps him. He abandons the Roberta persona and stealthily returns the stolen painting, drawing the wrath of the fraternity when they discover the missing artwork.
A sorority sister suspects Roberta after the painting’s disappearance, complicating Bobby’s dual life further. Mike arranges a date between Roberta and Wally [Patrick Richwood], one of the pledge brothers, to keep up appearances while Bobby struggles to balance love, loyalty, and honesty. In the midst of it all, Diana finally articulates the fundamental differences between them, hinting at the possibility of a real connection beyond the ruse. She also hints at what she knows about the Derry incident, prompting Bobby to rethink his approach and come clean.
As the semester winds down, Bobby confronts the deeper questions about gender and history in class, and the moment becomes a turning point when he tells the teacher the truth about his actions, opening himself up to real learning. He takes the field with his fraternity for one last game, hoping to prove himself not as a fake but as a person who can grow. In the final moments, Bobby delivers a passionate speech as Roberta, finally embracing his introspection in front of everyone, while Mike cheers him on. After the ceremony, Bobby’s dad comes to him and voices his love, and Bobby apologizes to Diana—the two slowly begin to mend what was strained, choosing a path forward together.
