Gray Baldwin (Heather Graham), a family oriented and quiet bachelorette, lives a close-knit life with her brother, Sam (Tom Cavanagh). Their lifestyle is generally co-dependent, involving them living together, going to dance classes together, etc. Gray and Sam's relationship has never been thought of as strange, but once a dinner party guest mistakes the siblings as a couple, Gray and Sam decide to venture outside of one another. While discussing with each other what they can do about their single lifestyles, and how they can "hook each other up" with a significant other, their conversation continues to the park, where Gray spots a possible girlfriend for Sam, Charlie Kelsey (Bridget Moynahan). Gray introduces herself, then Charlie to Sam, and they instantly bond, agreeing to see each other again.