Iris Simpkins, a society columnist for The Daily Telegraph in London, still loves her ex-boyfriend, Jasper Bloom, despite the fact that he cheated on her and is emotionally needy.

On Halloween night, 1998, at Cornell University, Tom Bailey, Jr. (Patrick Dempsey), in costume as Bill Clinton, slips into bed with his pre-arranged date, Monica.

Jane Nichols (Katherine Heigl) has been a bridesmaid for 27 weddings.

Ryden Malby graduates from college in the middle of the late-2000s recession and is forced to move back in with her parents, because her dream job has been given to her arrogant college nemesis Jessica Bard.

Kat Ellis (Debra Messing) is a single New Yorker who returns to her parents' house in London to be the maid of honor at her younger half sister Amy's (Amy Adams) wedding.

Moonlight in Vermont is the title of a 1943 American musical dramatic film. Vermont farm girl Gwen Harding goes a dance school in the city. She becomes semi-popular.

Lucy Kelson (Sandra Bullock) is an intelligent, highly-competent liberal lawyer who specializes in historic preservation, environmental law, and pro bono causes in New York City.

Jason is sitting on a bench in New York City waiting for someone to arrive.

Shy high school junior Lara Jean Covey writes letters to boys she feels an intense passion for before locking them away in her closet.

Jay Wheeler, the "black sheep" son of a rich family starts working as a janitor at a psychiatric hospital as part of his parole.

Grace Bennett (Selena Gomez) is a New York University bound, Texas high-school student who works as a waitress with her best friend, high school dropout Emma Perkins (Katie Cassidy) to earn money for a trip to Paris after graduation.

Five years after the first film, Mia Thermopolis has just graduated from Princeton University's Woodrow Wilson School and is returning to Genovia with her bodyguard, Joe.

In an opening scene, a group of men are interviewed regarding Christina Walters who introduce her as a player and a user of men in the swinging singles market.

Ashley Albright works at Braden & Co. Public Relations and has an extremely fortunate life, experiencing recurring strokes of good fortune since childhood.

Elle Evans and Lee Flynn have been best friends all their lives due to their mothers growing up together and having a deep bond.

Maggie Carpenter (Julia Roberts) is a spirited and attractive young woman who has had a number of unsuccessful relationships.

Rebecca "Becky" Bloomwood is a hardcore shopping addict who lives in New York City with her best friend Suze.

In New York City, high-strung equity trader Joy Ellis McNally is dumped by her fiancé at a surprise birthday party she throws for him.

Andie Anderson (Kate Hudson) is a writer for the women's magazine Composure as the "How to", subject-matter expert.

Ambitious San Francisco wedding planner Mary Fiore is re-introduced to childhood acquaintance Massimo by her father Salvatore, who wants them to marry, but Mary declines.