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.
| Actor | Role |
|---|---|
 Dakota FanningLilly Berger | Lilly Berger |
 Elizabeth OlsenGerry | Gerry |
 Boyd HolbrookDavid Avery | David Avery |
 Demi MooreKate | Kate |
 Richard DreyfussDanny | Danny |
 Ellen BarkinNorma Berger | Norma Berger |
 Peter SarsgaardFitzsimmons | Fitzsimmons |
 Clark GreggEdward Berger | Edward Berger |
 Kiernan ShipkaEleanor Berger | Eleanor Berger |
 Clare FoleyPhoebe Berger | Phoebe Berger |
 Owen CampbellKarl | Karl |
| RRoslyn CurryJoy | Joy |
 Lenny PlattBeach Boy | Beach Boy |