In order to gain her boyfriend's respect, a New York socialite takes a job as a nanny.

Jackie is a recently divorced woman with two children who is about to turn forty. Her best friend hooks her up with a trip to the Islands for a little vacation getaway. Finding herself alone, she decides to have a scorching romance with a sexy younger man. Her children, friends, ex-husband and her common sense tell her something completely different from what her heart is saying. But, Jackie realizes that at 40, her life is just beginning.