Jenna is a pregnant, unhappily married waitress in the deep south. She meets a newcomer to her town and falls into an unlikely relationship as a last attempt at happiness.
Jenna is unhappily married, squirreling away money, and hoping to win a pie-baking contest so, with the prize money, she'll have enough cash to leave her husband Earl. She finds herself pregnant, which throws her plans awry. She bakes phenomenal pies at Joe's diner, listens to old Joe's wisdom, tolerates her sour boss Cal, is friends with Dawn and Becky (her fellow waitresses), and finds a mutual attraction with the new doctor in town. As the pregnancy advances, life with Earl seems less tolerable, a way out less clear, and the affair with the doctor complicated by his marriage. What options does a waitress have?
Jenna is a small-town waitress at Joe's Diner, who has a great knack at making delicious pies there. However, Jenna is in an unhappy marriage to her controlling and immature husband, Earl, who always takes the money she works hard for, but Jenna keeps some of it hidden from him. Jenna suddenly finds her life has taken an unexpected turn when she discovers she's pregnant with Earl's baby. But the unhappy pregnancy changes Jenna's life as she becomes determined to win the $25,000 pie contest prize money and begins an affair with her handsome, married gynecologist that gives her confidence and an attempt at happiness.
In the American south, Jenna Hunterson is a waitress at Joe's Pie Diner in Redhook. Along with Becky and Dawn, the other waitresses, Jenna makes the pies for the diner, she who is known in her circles as the best. She funnels her energies into her creative pie making, this love and skill which was passed down to her by her now deceased mother. Her newer pie creations are always a reflection of what is happening in her life at the time. Otherwise, her life is a fairly unhappy one because of the people in her life. Cal, the diner's manager, is always barking orders, never providing compliments. Jenna more often than not is tasked with waiting on Joe, the elderly owner of the diner, she who has to cater to his different but constantly demanding order peccadilloes or else. Even though Becky and Dawn are her close friends and confidantes, their lives are as screwed up as Jenna's and thus they can't provide her much constructive guidance. However, even Becky and Dawn would rather be themselves than Jenna, largely because of Jenna's husband, Earl, who she fears and hates because of his controlling behavior. That control includes keeping all the household money, even her diner wages and tips, and treating her like his sole property. She doesn't have the means to leave him, she secretly hiding money from him to enter the United States of Pie bake off with a $25,000 first prize, the contest which he would not allow her to enter if he knew what she was doing. That control is why she is dismayed to learn that she is pregnant with his baby, from one of their infrequent sexual encounters when he got her drunk. Although she plans to keep the baby, she plans not to tell him until absolutely necessary, and treat the pregnancy as a cold-hearted fact with respect but not love, as she realizes this baby will tie her more to him. As Jenna goes through her pregnancy, she has to deal with a new physician, Dr. Jim Pomatter, a nervous but otherwise sweet man. Although Dr. Pomatter is also married, he and Jenna embark on an affair, and although they seem to be falling in love, she doesn't want him to save her. If Jenna can delve under the surface of these relationships, she may get a clearer picture of what her post-delivery life as a mother may be like.
- Jenna (Keri Russell), a waitress living in the American South (though the movie was actually shot in and around Canyon Country, California), is trapped in an unhappy marriage to a jealous, controlling, and abusive man named Earl (Jeremy Sisto). She works in Joe's Pie Diner, where her job includes creating the unique pies of her life, such as the "I Don't Want Earl's Baby" pie (aka Bad Baby pie) she invents after her unwanted pregnancy is confirmed. Jenna longs to run away from her dismal situation, and is hiding money to do so. Her only friends are Becky (Cheryl Hines) and Dawn (Adrienne Shelly), her fellow waitresses, and Joe (Andy Griffith), the curmudgeonly diner owner who encourages her to escape from her bad marriage and begin a new life elsewhere.
Jenna's life changes dramatically after she meets her OB/GYN, Jim Pomatter (Nathan Fillion), a Connecticut transplant who has moved to the small town to accommodate his wife, who is completing her residency at the local hospital. Jenna and Jim embark on a passionate affair, and eventually Jenna thinks of him as not only her lover, but best friend as well.
Jenna begins to keep a journal, addressing her thoughts to her unborn child. Between these entries and the various pies she creates, the audience witnesses her innermost hopes and dreams, concerns and fears, and slowly growing feelings for the baby she insisted she didn't want.
Reluctant mother Jenna instantly falls in love with the baby girl she names Lulu. When Earl reminds Jenna of her promise earlier not to love the baby more than she does him, she gains the strength to tell him she hasn't loved him in years and will no longer put up with his possessive and abusive ways and wants a divorce. In retaliation he refuses to pay the hospital bills, and she is abruptly discharged.
As Becky and Dawn are helping her prepare to leave the hospital to live with Dawn and her husband until she can formulate a plan for her future, Jenna remembers an envelope Joe had delivered to her when he too was admitted as a patient. In it she finds a handmade card with a sketch of her, a check for $270,450, and a message urging her to start fresh.
As she departs from the hospital, Jenna ends her relationship with Jim and begins her life anew. An epilogue shows Jenna winning a pie contest and as the new owner of the diner where she worked, now called Lulu's Pies, serving brightly colored pies to her customers and friends. The final shot shows her walking home with toddler Lulu (played by Shelly's actual daughter, Sophie).