Kansas City investment broker Karen Reese has had a long history of bad relationships with men. Her marriage to John Reese was short-lived because of John's controlling nature. It nonetheless resulted in a child, Karen who has custody of now nine year old Justin. John is largely out of Justin's life, which bothers Karen if only because of Justin's want for his father to be truly a father figure. Karen just broke up with her latest boyfriend Randy Stroud for many of the same reasons she broke up with John before him. Karen's sister, Donna Eckhart, believes Karen sabotages many of her relationships out of fear. Karen's boss, Alex, is interested in her romantically, but she believes he is too young for her despite his devotion. When Karen meets venture capital consultant Denis Teague, who is Karen's brother-in-law Lenny Eckhart's new work colleague, Karen thinks that her long streak of bad relationships may have come to an end. Denis is handsome and attentive. And after a rocky start ...