After getting dumped for the 11th time in a row, Frankie discovers that she has a "loser in love" gene, which predisposes her to chronic failure and rejection for the rest of her life. She decides to embark on a quest to change her romantic future.
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.
When a young boy makes a wish at a carnival machine to be big—he wakes up the following morning to find that it has been granted and his body has grown older overnight. But he is still the same 13-year-old boy inside. Now he must learn how to cope with the unfamiliar world of grown-ups including getting a job and having his first romantic encounter with a woman.
Lovestruck Dustin is dating Alexis, his ideal girlfriend, but when she dumps him for coming on too strong, Dustin takes drastic measures to win her back. He asks his best friend Tank to take her on the worst rebound date imaginable - his side job - so that she will come running back to him, and Tank reluctantly agrees. However, Alexis is more than a match for Tank's shock tactics and he begins to really fall for her, leaving him torn between loyalty to Dustin and his growing attraction toward Alexis.
Quinn, a neurotic man, is diagnosed with a harmless eye condition and soon after his life spirals out of control. He second-guesses his plans to propose to his longtime girlfriend, Devon, after his beautiful coworker, Kelsey, confesses that she has a crush on him. After a conversation with his best friend, Jameson, he clumsily tries to explain his doubts to Devon, but his possible proposal turns into a break-up. When Devon flees to Paris, he follows her in a last-ditch effort to win back "the one."
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.
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?
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.
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.
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.
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