Allison, a successful, driven doctor runs into Amy, a larger than life, eccentric woman who claims to be her "guardian angel", and whose mission is to help Allison loosen up and see her life from a new perspective.
Allison asks New Kids On The Block favorite Joey McIntyre to help her patch up a relationship with an old friend as part of a lesson Amy's trying to teach her about facing her fears.
Allison takes Amy to a nightclub to help her stop over-thinking everything and let loose, while Marv, suspicious of his daughter's odd new friend, does a background check on Amy.
Marv balks at allowing Allison to make some changes to their dermatology practice, so Amy creates a temporary position for herself in order to help them work out their differences.
Amy's plan to get Allison to stop caring about "looking stupid" backfires when Allison makes a spontaneous decision that leads her to meet her soulmate before she's supposed to.
Amy is required to perform 10 good deeds to earn her angel powers back after losing them by cheating at a game.
When Allison is struck with dating jitters, Amy suggests she have a "fling" to work out her nerves.
Allison feels nervous about dating and Amy comes up with the idea of having a fling to see if it works out her feelings.