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Baltimore-based friends and lovers, all in their 20s and 30s, try to navigate their way through the complexities of modern relationships. Beth (Jennifer Aniston) wants commitment from Neil (Ben Affleck), who sees nothing wrong with the status quo. Gigi (Ginnifer Goodwin) is tired of waiting by the phone, while Mary (Drew Barrymore) has a slew of supportive male friends, none of whom are straight. Meanwhile, Janine has trust issues with her husband, who can't trust himself around Anna.
Lucy Hill (Renée Zellweger), an ambitious executive, lives the high life in Miami. She loves climbing the corporate ladder as well as all the material goods that her success can buy. When she is offered a temporary assignment to restructure a factory in a backwater town, she eagerly accepts and anticipates a huge promotion in the pipeline. However, what Lucy gets is a life-changing experience and romance with the man of her dreams (Harry Connick Jr.).
Acerbic, selfish and widowed, literature professor Lawrence Wetherhold (Dennis Quaid) is estranged from his son and his overachieving teenage daughter. Just as he begins a relationship with a former student (Sarah Jessica Parker), Lawrence's ne'er-do-well adoptive brother (Thomas Haden Church) lands on his doorstep. Lawrence realizes he must make some changes in his life and reconnect with his children in order to get on with his life.
Discovered by blogger Perez Hilton, a woman gains a legion of followers as an online celebrity who battles cyberbullying. She must now wrestle with the pitfalls of fame while navigating an exciting but rocky relationship with a fitness entrepreneur.
After several years away, FBI agent Henry Durand (Colin Hanks) returns to find his mother, Marty (Meg Ryan), a much different person: Having long mourned for Henry's father, she is now embracing single life. One day, while Marty, Henry and his new fiancée, Emily (Selma Blair), are out for a walk, they meet Tommy (Antonio Banderas), a mysterious stranger, with whom Marty then becomes involved. However, through his FBI contacts, Henry learns that Tommy is suspected of being an art thief.
Single Jack (Philip Seymour Hoffman) drives a limo for a living and has a best friend, Clyde (John Ortiz), a married co-worker. Clyde and his wife decide to set up Jack with another friend, Connie (Amy Ryan). Jack and Connie hit it off, and a tentative romance blossoms, inspiring Jack to take cooking lessons, learn to swim, and apply for his dream job. However, as that relationship grows stronger, Clyde and his wife find their marriage crumbling.
At the start of the New Year, 32-year-old Bridget (Renée Zellweger) decides it's time to take control of her life -- and start keeping a diary. Now, the most provocative, erotic and hysterical book on her bedside table is the one she's writing. With a taste for adventure, and an opinion on every subject - from exercise to men to food to sex and everything in between - she's turning the page on a whole new life.
A couple's dream wedding sets the stage for a cultural clash when their families, who are from different sides of the tracks, come together for the ceremony.