Two friends, Ryan and Carmen, sit in a Melbourne playground at night discussing a practical joke they once played, but their recollections disagree on the finer details of the prank. They discuss a friend of theirs, Jack, who is moving overseas, and agree to get the old gang together for a final "heartbreak tour" before she leaves.
They meet up with their friends at a pub, where Carmen's boyfriend Tim is regaling them with an anecdote about how he once hooked up with a girl in the pub's toilet, and then had to avoid getting caught by her boyfriend. The five of them: Ryan, Carmen, Tim, Jack and Nick climb into Ryan's car, and drive to Carmen's old house where she lived with her ex-boyfriend Alan. The group recall when Jack and Nick (Ryan's cousin) had got together, and recall visiting the house for dinner. The next stop is a legendary house party in Fitzroy: Nick and Jack had broken up by this stage, and there is an awkward moment when they run into each other at the party. Jack and Nick have different recollections of their behaviour on the night, but in both accounts, a very drunk Nick turns up at Carmen, Ryan and Dave's house. He angrily hammers on Dave's door, accusing him of sleeping with Jack, and she comes out of the house and tells him to let it go. Ryan, however, recalls what actually happened: he sneaked around to the back of the house and saw Jack and Carmen together.
Outside Jack's old house, Ryan and Jack remember how they decorated her room with luminous stars. They are questioned by two police officers, who return to their car to smoke a joint. Boarding a bus to the waterfront, Ryan bares his soul about his unrequited love for Jack, and how he'd imagined himself being with her. He regrets not kissing her when they decorated her room, and wonders what would have happened if he had. Jack says nobody knows, and that each of their different recollections of the events of their lives means that everyone is the hero of their own story. Tim heads home, and the others jump off the pier into the water for a playful swim.