In an alternative 1990s a lonely, dinosaur-obsessed boy named Wyrm struggles to complete a unique school requirement in which students wear electronic collars that detach only upon engaging in their first kiss.
Josie Geller, a baby-faced junior copywriter at the Chicago Sun-Times, must pose as a student at her former high school to research contemporary teenage culture. With the help of her brother, Rob, Josie infiltrates the inner circle of the most popular clique on campus. But she hits a major snag in her investigation -- not to mention her own failed love life -- when she falls for her dreamy English teacher, Sam Coulson.
More than a dozen Angelenos navigate Valentine's Day from early morning until midnight. Three couples awake together, but each relationship will sputter. A grade-school boy wants flowers for his first true love. Two high school seniors plan first-time sex at noon. A TV sports reporter gets the assignment to find romance in LA. A star quarterback contemplates his future. Two strangers meet on a plane. Grandparents, together for years, face a crisis. An 'I Hate Valentine's Day' dinner beckons the lonely and the lied to.
Manhattanite Ashley is known to many as the luckiest woman around. After a chance encounter with a down-and-out young man, however, she realizes that she's swapped her fortune for his.
Giulia and Carlo have been happy together for three years, but Giulia's announcement that she is pregnant sends him into a secret panic. Terrified at his imminent entry into the adult world of irreversible responsibilities, Carlo finds himself tempted by a bewitching 18-year-old girl, Francesca, whom he meets by chance at a wedding. The possibility of one last youthful crazy fling before the impending prison of parenthood proves to be too attractive to resist.
When Zoe tires of looking for Mr. Right, she decides to have a baby on her own. But on the day she's artificially inseminated, she meets Stan, who seems to be just who she's been searching for all her life. Now, Zoe has to figure out how to make her two life's dreams fit with each other.
Writer Alex Sheldon must finish his novel within a month. If he doesn't, he won't get paid. And, if that happens, angry Mafia types to whom he owes money will come looking for him. In order to expedite things, Alex hires typist Emma Dinsmore and begins dictating his novel. The book is about a doomed love affair between a character similar to Alex and a character named Polina Delacroix. But, as Alex falls for Emma, his work takes a different turn.
When Gabriel and Emilie meet by chance, he offers her a ride, and they spend the evening talking, laughing and getting along famously. At the end of the night, Emilie declines Gabriel's offer of "a kiss without consequences". Emilie admonishes him that the kiss could have unexpected consequences, and tells him a story, unfolding in flashbacks, about the impossibility of indulging your desires without affecting someone else's life.
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