After her stay-at-home husband leaves her, a workaholic lawyer finds that she is not completely up to the tasks of caring for her young son, ailing father and household all by herself.
Dane Jensen is a driven, Chicago-based headhunter, working at a cut-throat job placement firm. When his boss pits Dane against Lynn Vogel, Dane's equally driven but polar-opposite rival at the firm, in a battle for control over the company. When his young son is then given a harrowing diagnosis, Dane is suddenly pulled between achieving his professional dream and spending time with the family that needs him now more than ever.
When a workaholic young executive is left at the altar, she ends up on her Caribbean honeymoon cruise with the last person she ever expected: her estranged and equally workaholic father. The two depart as strangers, but over the course of a few hilarious adventures, a couple of umbrella-clad cocktails and a whole lot of soul-searching, they return with a renewed appreciation for family and life.
A modern day train hopper fighting to be a successful musician and a single mom battling to maintain custody of her daughter defy their circumstances by coming together in a relationship that may change each other's lives forever.