When Jackie Warren's husband goes through a mid-life crisis and announces that he is having an affair, she decides to make a new life for herself. Once a wealthy socialite, she enters the work force for the first time and gets her own place to live. Jackie squeezes into a less-than-lavish but charming house owned by former football player Marion Hill, whose stellar career was ruined by a freak acc...

When a female bully at school harasses Austin, he asks Jackie and Marion for advice. Unfortunately, he must choose between two opposing philosophies: Jackie says he should protect himself and fight back, while Marion advocates a non-violent approach. Meanwhile, Tiffany fights with her boyfriend on the telephone and agonizes about whether to call him back or wait for him to call her.

Jackie is out of the house celebrating her son Austin's birthday, so Marion plans a reunion with his ex-girlfriend, who thinks he still has an active football career. But Jackie unexpectedly brings the party back to the house and upsets Marion's romantic evening. Meanwhile, Heather dates a single father and asks Jackie's advice on bonding with his daughter.

It's been nearly 20 years since Jackie went on a date, but Marion tries to get her to meet men at a popular night club. However, when Marion's former grade school football coach comes for a visit, Jackie finds an eligible bachelor in her own living room.

Austin persuades Jackie to continue the family tradition of visiting their mountain cabin at the beginning of the spring season. But when Jackie's car breaks down, Marion must drive them. Their plans are thrown into further turmoil by Jackie's ex-husband Milton, who brought his new young bride to the cabin for a romantic weekend.

Jackie and Heather help Marion get an audition for a sportscaster job on a local news show. For the audition, he interviews basketball star Spud Webb. Marion gets the job! But when he refuses to do the broadcast without his lucky hat, the station owner issues an ultimatum: either the hat goes or Marion goes. Meanwhile, Tiffany participates in a school charity drive to get closer to a cute classmat...