Celeste and Jesse met in high school and got married young. They laugh at the same jokes and finish each other’s sentences. They are forever linked in their friends’ minds as the perfect couple – she, a high-powered businesswoman and budding novelist; he, a free spirit who keeps things from getting boring. Their only problem is that they have decided to get divorced. Can their perfect relationship withstand this minor setback?
As she reaches her mid-thirties and quits her lucrative job, singleton Olivia finds herself unsure about her future and her relationships with her successful and wealthy friends. She begins to envy the security of her richer friends and, although their lives may seem easier, Olivia's friends have their problems too: screenwriters Christine and Patrick are unable to collaborate on their latest project, Jane and Aaron have lost the romance in their relationship, and Franny and Matt have difficulties handling the demands of parenthood.
When record store owner and compulsive list-compiler Rob Gordon gets dumped by his long-time girlfriend, Laura, because he hasn't changed since they met, he revisits his top five breakups of all time in order to figure out what went wrong. As he examines his failed attempts at romance and happiness, the process finds him being dragged, kicking and screaming, into adulthood.
Annie is stuck in a long-term relationship with Duncan – an obsessive fan of obscure rocker Tucker Crowe. When the acoustic demo of Tucker's hit record from 25 years ago surfaces, its discovery leads to a life-changing encounter with the elusive rocker himself.
Bernie and Joan are two fiery flirters who are passionate about everything from hookups to breakups and each other. When he sets up his best friend, Danny, with her roommate, Debbie, the sparks soon fly as they try to navigate the relationship minefields from the bar to the bedroom and are eventually put to the test in the real world.
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.
After serving five years in prison, wild child Tanya looks to her buttoned-up, by-the-book sister Danica to help her get back on her feet. The feisty ex-con becomes suspicious and concerned when Danica tells her that she's in a long-distance, online relationship with a mysterious man she's never seen. As the polar opposites start to collide, Tanya soon discovers that her sibling's picture-perfect life may not be what it seems.
Longtime single friends Ben and Alice agree to be each other's respective plus one at every wedding they're invited to during a busy summer of wedding fever.
Dog and Mirales have been friends since childhood, and live in a small village in the south of France. They spend most of the day hanging around in the streets. To kill time, Mirales has got into the habit of teasing Dog, to the extent that he has become a sort of whipping boy. But one summer, Dog meets Elsa, and they fall in love. Eaten away with jealousy, Mirales will have to get over his past to be able to grow and find his place…
When Ben Wrightman, a young teacher, begins dating pretty businesswoman Lindsey Meeks, the two don't seem to have a lot of the same interests, but they fall in love, regardless. Their romance goes well until baseball season begins, and Lindsey soon realizes that Ben is completely obsessed with the Boston Red Sox. Though she tries to understand Ben's passionate team loyalty, eventually it threatens to end their otherwise happy relationship.
In the wake of their friends' marriages and eventual offspring, longtime pals Julie and Jason decide to have a child together without becoming a couple. By becoming "time-share" parents, they reason, they can experience the joys of parenthood without significantly curbing their personal freedom. However, when Julie and Jason both become involved with others, they discover that they secretly harbor romantic feelings for each other.
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