Spending long, languid weekends in St. Thomas would seem like a dream job for most people. For single, thirty-something Ashley Farrell, however, it comes with the humiliation of having to act as chaperone for the varlous bachelor and bachelorette winners of a popular TV dating show. But this dead-end junket shows signs of new life. Between safeguarding the morals of curvaceous Melissa and voracious Randy and avoiding the diamond-dripping wife of a reputed crime boss, Ashley is attracting the serious attention of a tall, deliciously sexy stranger she met on the airplane.