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.
When Allison tries to convince Marv to make some changes at their dermatology practice, he balks at what she has planned. As a result, Amy takes it upon herself to create a temporary job at the office to help them work things out.
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.
When Allison begins dating a new guy, Amy tries to finagle their first kiss before the "window of opportunity" closes to turn things into a lasting relationship.
When Allison reveals how stressful Thanksgiving was after the loss of her mother, Amy suggests a "Funsgiving" instead, with games and untraditional food.
