Teena Brandon (HILARY SWANK) is a young woman from Lincoln, Nebraska who's so confused about her sexual identity that she's cut her hair short and switched her name around to Brandon Teena. Sporting the look and attitude of a young, but tough "pretty boy," Brandon arrives in a bar in the small town of Falls City while awaiting a court date for grand theft auto back home.
There, "he" meets and tries to pick up Candace (ALICIA GORANSON), one of any number of young women in town with limited futures and little prospect of ever leaving. When Brandon gets into a fight with a much larger and older man trying to hit on Candace, her ex-con friend, John (PETER SARSGAARD), steps in and takes care of the lech.
Soon, Brandon falls in with John's clique of small town friends including fellow ex-con, Tom (BRENDAN SEXTON III) and Candace's girlfriends, Kate (ALISON FOLLAND) and Lana (CHLOň SEVIGNY), the latter of whom is completely disillusioned with her small town existence.
Yet, some sparks enter her life when she and Brandon immediately hit it off. As they spend more time hanging out with their friends and at her mom's (JEANNETTA ARNETTE) house, the two become an item. As their relationship turns sexual and arouses John's jealousy, Brandon tries to keep his cross gender identity a secret while never imagining what reaction awaits him should the others find out he's really a young woman.