Dr. Lenny Faulkner, a single, African American doctor is living a charmed life in Atlanta; compared to the poor childhood she experienced growing up in Madoosa County, a small southeast section of Georgia that reeks of the local box manufacturing plant. Lenny is dedicated to the care and treatment of her female patients. Lenny has been successful in achieving all her goals except one: She yearns to marry her live-in love Ralph and start a family.
In fact, the alarm on Lenny's biological clock is ringing loud and clear---she's turning thirty-five, but Ralph, doesn't hear it. Instead of proposing, he abruptly ends their nine-year relationship, empties their joint bank account and runs off with another woman. Adding to Lenny's misery, she learns that her mother is dying of cancer, with only a few months to live.
Feeling utterly defeated, she discovers her fifth grade diary, which contains a list of rules she had created to live by. Reading them after so many years, Lenny realizes that she has somehow buried the intensity she demonstrated in her youth that helped her get out of Madoosa County.
The diary becomes the impetus Lenny needs to start taking complete charge of her life again. She discovers that Ralph leaving isn't such a loss and that her newfound strength has opened the door to new possibilities, including love.