Two twenty-somethings, both reeling from bad break-ups, connect over the course of an eventful day in South London – helping each other deal with their nightmare exes, and potentially restoring their faith in romance.
Sophie reflects on the shared joy and private melancholy of a holiday she took with her father twenty years earlier. Memories real and imagined fill the gaps between miniDV footage as she tries to reconcile the father she knew with the man she didn't.
Three friends get together and bury a box making a pact to open it at midnight at their high school graduation. In the little town in Georgia that they live in, things soon change. One is little miss perfect, one is an engaged prom queen, and the other is a pregnant outcast. The night of graduation, they open the box and they strike up a conversation. All of a sudden, one brings up the topic of her going to Los Angeles for a record contract audition. They all decide to go together and they leave. With a little money, they set out on the road with a guy named Ben. When one of them tells the other a rumor that he might be a homicidal maniac they are all scared of him. When they reach LA, Lucy falls in love with Ben and against her father's wishes, she stays and she goes to the audition.
Pledging to keep herself from being the oldest and the only woman in her entire family never to wed, Montana embarks on a thirty-day, thirty-thousand-mile expedition to charm a potential suitor into becoming her fiancé.
Kasie, stuck in LA’s Koreatown, works as a karaoke hostess getting paid for her companionship by drunken men. When her dad’s hospice nurse quits she reconnects with her estranged brother, Carey, forcing them to enter a period of intense self-reflection as their single father who raised them nears death.
A couple of angels, O'Reilly and Jackson, are sent to Earth to make sure that their next supervised love-connection succeeds. They follow Celine, a spoiled rich girl who has just accidentally shot a suitor and, due to a misunderstanding, is kidnapped by janitor Robert. Although Celine quickly frees herself, she stays with Robert for thrills. O'Reilly and Jackson pursue, hoping to unite the prospective lovers.
When recently single Steven moves into his new apartment, cable guy Chip comes to hook him up—and doesn't let go. Initially, Chip is just overzealous in his desire to be Steven's pal, but when Steven tries to end the 'friendship', Chip shows his dark side. He begins stalking Steven, who's left to fend for himself because no one else can believe Chip's capable of such behaviour.
Bob Harris (played by Bill Murray) is an American film actor, far past his prime. He visits Tokyo to appear in commercials, and he meets Charlotte (Scarlett Johannson), the young wife of a visiting photographer. Bored and weary, Bob and Charlotte make ideal if improbable travelling companions. Scarlet is looking for "her place in life," and Bob is tolerating a mediocre stateside marriage. Both separately and together, they live the experience of the American in Tokyo. Bob and Charlotte suffer both confusion and hilarity due to the cultural and language differences between themselves and the Japanese. As the relationship between Bob and Charlotte deepens, they come to the realization that their visits to Japan, and one another, must soon end. Or must they?