It is spring. Randy Dean is a 17-year-old student in her final year with poor grades, only one friend - Frank, a gay Latino - secret cigarette and marijuana habits and a cashier’s job at a gas station with fellow worker Regina. Shunned by other students for her tomboyish personality and appearance, she spends most of her free time either by herself or in illicit meetings with her romantic partner Wendy, a married woman who drops by the gas station when it pleases her, even though Randy knows they are in a dead-end relationship. Randy lives with her lesbian aunt Rebecca and her girlfriend Vicky, as well as Rebecca's ex-girlfriend Lena, who has no place to stay and is living with them until she finds somewhere else she can go to.
One day Evie Roy stops in a pristine Range Rover, unsure if her tires need air. Randy recognizes her from school and talks to her for the first time. Evie is an only child living with her well-off, cultured mother, Evelyn, who has a difficult relationship with her remarried husband. Randy and Evie start passing notes in school and hanging out with each other, although Evie does not reveal this to her cliquish friends. During this time, Randy is approached by Wendy's jealous husband Ali at the gas station, who grabs Randy and warns her to stay away from his wife. Randy spends much of her time with Evie hanging out in meadows, trading music (opera and Mozart from Evie, punk rock from Randy) and talking. When Wendy next visits her, Randy rejects her, telling her she has a new girlfriend, Evie.
Evie breaks up with her boyfriend Hayjay after he complains of her distant attitude towards him. Later, apparently on a spur of the moment, she lends Randy a copy of Walt Whitman’s Leaves of Grass, which Randy starts to devour. Inviting Evie to her family’s small house for dinner one evening, Randy reveals to her that she has lived with Rebecca and Vicky since Randy's devoutly religious mother abandoned her to devote all her time to an Operation Rescue-like group. On the front steps of Rebecca's house, they kiss for the first time. Evie records it in her diary later, apparently wondering what it all means.
Randy and Evie experiment with how "out" they can be as lesbians, nervously holding hands at a local diner. Remembering Randy’s warning of how intolerant the town can be, Evie nevertheless breaks the news to her three closest friends. One girl is supportive (if confused), but the other two are hostile to the idea: one of them says, “God, Evie, if you were gonna turn gay you think you could at least choose someone who’s pretty.” Meanwhile, Randy’s grades continue to plummet and the school warns her she will not graduate; Randy hides this information from Rebecca. When Evie’s mother leaves on a business trip, the girls take the opportunity to cook a huge meal, indulging in wine and marijuana. That night, they make love, then fall asleep in Evie’s mother’s bed.
The next morning, it is Evie's 18th birthday; Evelyn returns prematurely with presents for her, but is shocked by the mess in the kitchen and the rest of the house. Furiously searching the upstairs, she discovers Evie and Randy, but only realizes Randy is a girl when she runs past her on her way out. Rebecca, who has learned that Randy will not be graduating high school, goes over to go to Frank’s house with Vicky and Lena, where Randy had told them she would be staying the night. Rebecca threatens Frank until, panicked, he turns over Evie’s phone number. She calls, but Evie and Randy have already absconded and she is left talking to a furious Evelyn.
Evie and Randy, crying, scared and accusatory, take refuge in a motel. Randy finally calls Wendy, who comes out, pays for the room and tries to comfort the girls. Ali sees her car in the parking lot, however, and comes bursting in, eventually attracting Evelyn, Rebecca, Vicky, Lena, Frank, and Evie’s three friends, who were driving past reading aloud from Rita Mae Brown’s Rubyfruit Jungle (apparently still processing Evie’s news). The movie ends with Randy and Evie kissing and hugging in the open motel room doorway while everyone else argues in the background at top volume.Laurel Holloman — Randall "Randy" Dean
Nicole Ari Parker — Evelyn "Evie" Roy Jr
Maggie Moore — Wendy
Kate Stafford — Rebecca Dean
Sabrina Artel — Vicky
Nelson Rodríguez — Frank
Dale Dickey — Regina
Katlin Tyler — Girl #1
Anna Padgett — Girl #2
Chelsea Cattouse # 3
John Elsen - Ali, Wendy's husband
Stephanie Berry — Evelyn Roy
Toby Poser — Lena
Andrew Wright — Hayjay
Babs Davy - Waitress
Lillian Kiesler - Old Lady #1
Maryette Charlton - Old Lady #2
Maggenti had started a script with an image in her head of a tomboy with love notes in her back pocket, and gradually added more characters such as the tomboy’s family and her love interest. Later, she realized this character was based on her first girlfriend. Between 1992 and 1994 her script, "a dark look at the middle and end of the girls' relationship", grew until Maggenti abandoned it.
However, the film’s future associate producer, Melissa Painter, convinced Maggenti to shop the story around as an independent film - two producers wanted a pivotal element which would make two very different girls cross paths, and Maggenti then improvised the story that formed the beginning of their relationship. The producers were delighted with this, so Maggenti wrote a new script which she finished in eight days. She found she had surprised herself in that her script was now a comedic farce; the story wasn't about gay love or coming out, but about first love between teenagers.
Shooting was completed in 21 days. Scenes taking place at Randy and Evie's high school were filmed in divisions of The Horace Mann School, in Riverdale, Bronx.
The Incredibly True Adventure of Two Girls in Love was originally released on June 16, 1995 in the United States, with the film being released into Australian theatres on March 28, 1996 and UK theatres on September 10, 1996. It generated good notices and publicity at the 1995 Sundance Film Festival, where the film was released on January 23. It also won a GLAAD Media Award for Outstanding Film – Limited Release in 1996, with its success launching the film careers of the movie's fronting actresses Laurel Holloman, Nicole Ari Parker and Dale Dickey.