My Best Friend's Wedding (1997)

Julianne Potter (Julia Roberts), a 27-year-old New York restaurant critic, receives a call from her longtime friend Michael O'Neal (Dermot Mulroney). In college, the two made an agreement that if neither of them were married by the time they turned 28, they would marry each other. Three weeks before her 28th birthday, Michael tells her that in four days, he will marry Kimmy Wallace (Cameron Diaz), a 20-year-old University of Chicago student from a wealthy family.


Julianne is upset that Michael will marry someone so wrong for him, and someone he has known for such a short period of time. She realizes that she is in love with Michael, and heads to Chicago, intent on sabotaging his wedding. Soon after arriving she meets Kimmy, who asks her to be the maid of honor. This sets off a comical scenario in which Julianne must pretend to be the dutiful maid of honor while secretly scheming ways to prevent the wedding from happening. She engages in petty sabotage - for example, taking Kimmy and Michael to a karaoke bar after discovering that Kimmy is a terrible singer - and later asks her gay friend George Downes (Rupert Everett) to pretend they are engaged, hoping to make Michael jealous.


When these tactics fail, George persuades Julianne to do the obvious: tell Michael she is in love with him. One morning, Michael gets Julianne alone and tells her that it'll be the last time they ever get to be alone. He expresses some skepticism in marrying Kimmy, explaining that he and Kimmy don't share a special song like he and Julianne do. Michael discreetly gives Julianne the invitation to tell him she's in love with him, but she lets the moment "pass her by." Michael starts singing their song as he grabs Julianne and holds her while they dance one last time. The next morning which happens to be the wedding day, they take a walk and Julianne confesses her love to Michael, asks him to marry her instead, and passionately kisses him. Kimmy witnesses this and runs off, but Michael chases her.


Julianne pursues him but finally realizes Michael loves Kimmy. She apologizes and explains to Kimmy that she kissed Michael unexpectedly, but he didn't kiss her back because he was in love with Kimmy.


After the wedding Julianne tells Michael that he and Kimmy can use their special song until they find one of their own, essentially acting like a true best friend (possibly for the first time). Julianne wishes them well, consoled by George.