An unlikely friendship kindles between a struggling stand-up comedian from L.A. — forced to move back home to Eastern Long Island with his tail between his legs — and a tragically flawed, but charming and charismatic, alcoholic dermatologist. Discovering to be kindred spirits, each helps the other find healing, in addition to the confidence to face the "failures" in their lives.

Two overworked and underpaid assistants come up with a plan to get their bosses off their backs by setting them up with each other.

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.