When Jamie's plan to propose to Fancy fails, he decides to break up with her. But when he leaves the engagement ring at her apartment, Jamie and his friends must get it back before she finds it.
Phil and Mouse take Jamie to the club after his breakup with Fancy. After failing to pickup ladies, he meets a girl named Nancy who has a lot of things in common with Fancy.
After going through a series of low paying jobs, Jamie finally gets a break and records an original songs for a record producer, but the arrangement might not be as legitimate as Jamie thinks.
Jamie spends the night at Fancy's, leading to an awkward morning for the former couple. Tension increases when Jamie sees Fancy at a party with another man.
Jamie refuses to sign with a record company. Instead he tries to sell his CDs over the Internet.
Helen is opposed to Jamie filming a music video in the hotel due to its sexual content. The actress slated to appear in the video also objects to the video because of her lack of wardrobe.
Fancy nurses Jamie after he gets sick from Japanese food. He fakes a relapse the next day to prevent Fancy from going out with another man.
Jamie thinks Fancy is involved with NBA superstar Kevin Garnett, who is at the hotel for a press conference, when he finds a pair of size 22 sneakers under her bed.
When he strikes out with Fancy after a bowling game, Jamie calls on Cupid to help win her over. Meanwhile, Mouse starts dating a woman who he met using Cupid's help.
Jamie finds out Fancy is auditioning male dancers for her bachelorette party after they each promised not to have a party like that. So Jamie and Mouse set up a bachelor party.
Junior and Helen announce they are retiring the hotel to Jamie and Fancy, not knowing Fancy is considering a job in New York. Meanwhile, Braxton feels unappreciated when he doesn't get the hotel, after all his hard work.
Jamie and Fancy's big day arrives as Jamie rents a tuxedo and return to the event on time as the bride, her parents, and Jamie's mother anxiously await his arrival.