When Harry Met Sally...

For a long time, Natalie, an Australian architect living in New York City, had always believed that what she had seen in rom-coms is all fantasy. But after thwarting a mugger at a subway station only to be knocked out while fleeing, Natalie wakes up and discovers that her life has suddenly become her worst nightmare—a romantic comedy—and she is the leading lady.

While dining out with friends, Sy suggests the difficulty of separating comedy from tragedy. To illustrate his point, he tells his guests two parallel stories about Melinda ; both versions have the same basic elements, but one take on her state of affairs leans toward levity, while the other is full of anguish. Each story involves Melinda coping with a recent divorce through substance abuse while beginning a romantic relationship with a close friend's husband.

A pair of buddies conspire to save their best friend from marrying the wrong woman, a cold-hearted beauty who snatches him from them and breaks up their Neil Diamond cover band.

Arthur is a 30-year-old child who will inherit $750 million if he complies with his family's demands and marries the woman of their choosing.