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 Lily (Dakota Fanning) and Gerry (Elizabeth Olsen), home for one last New York summer, make a pact to lose their virginity before leaving for college. But when they both fall for the same handsome artist David Avery (Boyd Holbrook) and Lily starts seeing him in secret, a lifelong friendship is tested.
The film deals with female sexuality and friendship in a way we haven't seen before. These girls will be stunning young women in a couple of years, but they've struggled through high school with only each other. Most of us have been there. 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 feels suffocated in this completely dysfunctional relationship. In contrast Gerry's parents Kate (Demi Moore) and Danny (Richard Dreyfuss) are ultra liberal & provide a much more open & comforting environment to Gerry.Lilly and Gerry meet David at this part time job when he is selling ice cream. Gerry 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 then learns that Gerry has a thing for David & she is pursuing him.
Lilly works part time at a NY tour operator company and her boss Fitzsimmons (Peter Sarsgaard) has a thing for her.Lilly meets David secretly & kisses him passionately. She inquires David about his blossoming relationship with Gerry, which he refuses to answer. Lilly & David then have sex & Lilly loses her virginity to David. Gerry keeps calling David, but he doesn't show a lot of interest in her. Gerry tells everything to Lilly, but she says nothing back and continues to have sex with David.In the meantime Gerry's father dies & she is devastated. In her most difficult time, Gerry confesses that all she can think about is David. Lilly still doesn't come clean. Lilly starts avoiding David & then actively pushes him away.
Gerry invites David to attend her father's funeral and David goes without Lilly. In a weak moment Gerry asks David to have sex with her & he agrees. The next day Lilly listens Stoically when Gerry tells her that she has slept with David.In desperation, Lilly wants to have sex with her boss Fitzsimmons. She kisses him & has him ready, but then panics & does a KLPd on him. She meets David & tells him that she knows he slept with Gerry and that she has slept with Fitzsimmons.Gerry wont stop obsessing about David & Lilly finally tells her to get over it. David meets Lilly & begs her to tell Gerry the truth, but Lilly is afraid that Gerry would discard Lilly from her life. David meets Gerry one more time & tells her that he is leaving for Paris for good.
Lilly meets David before he leaves for Paris & he kisses her in the open street, which Gerry watches. Gerry confronts Lilly after David leaves & Lilly says that David was seeing Lilly for the summer before Gerry's dad died & then Lilly pushed David away so that he could have a relationship with & comfort Gerry. Gerry is angry.
A few days later, Gerry receives mail from David, addressed to Lilly & this makes her go meet Lilly. Gerry admits that she never slept with David. Lilly & Gerry make up and decide to remain friends forever.
