Demetri Chicopoulos (Robert Krantz) is living a charmed life. He is the host of his hit, daytime talk show, Daytime with Demetri. However, we soon learn that with a recent divorce and the passing of his mother, Demetri's life is more pain than charmed. In a prayerful moment, Demetri kneels and asks God if he could just relive one week of his life. He knows things would turn out differently. Demetri rises and suddenly meets... his Guardian Angel (Tom Arnold). Well, not exactly the type of Guardian Angel one hopes for. The Guardian Angel tells Demetri God heard his prayer... Demetri will get to relive one week of his life. What happens next will change Demetri's life forever.
Waymon has a great job in real estate and a promising future, but he's also trapped in a loveless longterm relationship. He meets Natalie, a beautiful club-hopping hipster, and quickly falls in love. Realizing he's just not cool enough to attract her on his own, he seeks the help of his friend Bobby, a free-spirited smooth talker who works in the mail room at Waymon's firm and utilizes the predicament as leverage to advance in the company.