Plot

Two New York City girls make a pact to lose their virginity during their first summer out of high school. When they both fall for the same street artist, the friends find their connection tested for the first time.

The summer before college presents two best friends, Lilly and Gerri, with the opportunity to shed their good girl images. Both girls want to lose their virginity and explore another side of who they are. But their dark and different home lives and the introduction of a bad boy, threaten to destroy their friendship without it being the nice coming-of-age summer that the two girls envisioned.—Anne Campbell

Best friends Lilly (Dakota Fanning) and Gerri (Elizabeth Olsen), home for one last New York summer, make a pact to lose their virginity before leaving for college. At Brighton Beach, they muse about swimming nude before Gerri suddenly takes off her shirt and runs into the water, followed by Lilly. On their way back home, they meet David, a guy selling ice cream. Lilly and Gerri meet David at this part time job when he is selling ice cream. They both fall for the same handsome artist David Avery (Boyd Holbrook).

These girls will be stunning young women in a couple of years, but they've struggled through high school with only each other. This is the summer where they finally get to touch real life.

Lilly comes from a wealthy family with doctor father Edward (Clark Gregg), who is cheating on his wife Norma (Ellen Barkin). Lilly had 2 sisters Eleanor (Kiernan Shipka) and Phoebe (Clare Foley). Lilly feels suffocated in this completely dysfunctional relationship.

In contrast Gerri's parents Kate (Demi Moore) and Danny (Richard Dreyfuss) are ultra-liberal & provide a much more open & comforting environment for Gerri. Lilly takes comfort in spending the evening with Gerri's family, who are loud and open in contrast to Lilly's stony mother and absent father. Lilly has been accepted to Yale and her orientation is scheduled for the first week of September.

Gerri is into David, while David is checking out Lilly. David takes a photo of Lilly's back & pastes posters over the city asking for her to meet him. Lilly finds the posters and is flattered. Lilly wants to tell Gerri about David, but Gerri starts talking about David first. So, Lilly never gets the chance to communicate her own attraction to David. Gerri exhibits an affection for him despite the lack of reciprocation, and despite neither girl knowing him well.

Lilly returns to the beach where she first met David and runs into him again. David asks Lilly out, and she agrees. Lily starts seeing him in secret, and her lifelong friendship with Gerri is tested. Lilly shares her address with David. Meanwhile, Gerri tries to get in touch with David over the phone to try and arrange a date with him.

Lilly works part time at a NY tour operator company and her boss Fitzsimmons (Peter Sarsgaard) has a thing for her. Lilly's boss flirts with her, offering lucrative night shifts with an obvious implication that he wants to have sex with her afterwards. Lilly's mother learns about her father's affair and asks him to leave, against Lilly's wishes. She begins to hang out with David and they kiss.

Gerri invites David to an open mic night where she sings a song she wrote for him, while out of her sight, David takes Lilly's hand and holds it under the table.

Lilly meets David secretly & kisses him passionately. She inquires David about his blossoming relationship with Gerri, which he refuses to answer. Walking home, she sees David waiting outside her house. They kiss and have sex in the garage.

The next morning Lilly bumps into her father who apologizes, asking her to have dinner with him, which she declines. Afterward, David sneaks in through the bathroom window. They shower together before spending the day flocking around the city. They arrive at a basketball court where a stylishly dressed man strips to his underwear and dances ballet in a liberating way. Kids join him while David videos.

Gerri keeps calling David, but he doesn't show a lot of interest in her. Gerri tells everything to Lilly, but she says nothing back and continues to have sex with David. In the meantime, Gerri's father dies & she is devastated. Lilly leaves David to be with a despairing Gerri. Sharing her grief encourages Lilly to ask her mother to forgive her father. In her most difficult time, Gerri confesses that all she can think about is David. Lilly still doesn't come clean. Guiltily, Lilly rejects David's attempts to meet again. He confronts her and she rebuffs him, asking him to meet up with Gerri, but is dismayed when David complies. He comforts Gerri and they kiss in her backyard garden, which Lilly sees.

Gerri invites David to attend her father's funeral and David goes without Lilly. In a weak moment Gerri asks David to have sex with her & he agrees. The next day Lilly listens Stoically when Gerri tells her that she has slept with David. In desperation, Lilly wants to have sex with her boss Fitzsimmons. They kiss in the tour boat, but then she changes her mind. However, when she confronts David about having sex with Gerri and he does not respond, she lies and tells him she had sex with her boss. The next day, Lilly surprisingly finds her parents cooking in the kitchen as her mother has forgiven her father. David shows up, claiming he didn't sleep with Gerri, and Lilly storms off.

Gerri won't stop obsessing about David & Lilly finally tells her to get over it. David meets Lilly & begs her to tell Gerri the truth, but Lilly is afraid that Gerri would discard Lilly from her life. David meets Gerri one more time & tells her that he is leaving for Paris for good.

Gerri tells Lilly that David is leaving for Paris, so Lilly finds him, admitting she didn't sleep with her boss. Angry, David warns her not to manipulate other people's feelings but still kisses her goodbye before leaving in a cab. As Lilly walks away, Gerri confronts her furiously, having overheard their conversation.

Lilly makes amends with her father, and he suggests she ask for forgiveness, but she does not take his advice. The morning before leaving for college, Gerri comes over with a photograph David sent her for Lilly, his way of making sure the girls saw each other before she left. Gerri reveals she never actually had sex with David, she asked him to, but he told her he was already in love with someone else. The girls make up, taking off their clothes to dance in the sprinklers.