Connor Mead, a successful fashion photographer and a Lothario keen on casual sex, goes to his younger brother's wedding to convince him not to marry. He arrives at his dead uncle's estate during the rehearsal the night before the wedding; he starts in, taking his brother aside, trashing marriage.

Jesse (Alyssa Milano) is a sweet and intelligent girl who is still looking for her Prince Charming, until he meets Ethan (Christopher Gorham), a writer who is on the brink of despair by a novel that was rejected by publishers. Jesse Ethan inspires, and begin a new chapter of her romantic life with a tremendous complication.