Maggie leaves her cheating husband and returns home to Indiana, where she plans to stay for only 6 months. She finds that her mother hasn't changed her bedroom in the fifteen years since she'd left and its also time for her high school reunion. She applies for a job, but finds the woman in charge of the interview, Rachel, still holds a grudge against her from high school. Seems Maggie got everything in high school that Rachel ever wanted, including Bobby Campanella. Rachel still wants Bobby (who is available) and she wants to know if Maggie is back to get together with him. Later when she is stressed out, Maggie rants about all her old friends still being stuck in high school. Out on the front porch, she and Bobby do get together and they do more than they ever did in high school. Maggie works to make amends with her other friends and later at the reunion, Rachel finds out about Maggie and Bobby.

Maggie goes back to plan A, something she wrote in her diary in years ago. Get a fabulous job in fashion, move out of mom's house, live happily ever after with Bobby and get a pony. Unfortunately, finding a job isn't going as well as she'd hoped and her relationship with Bobby might take her down the same path she's already been down. She calls it off with Bobby and ultimately finds herself faced with trying to get the job that Rachel still has available at her store.

Maggie is nearly in a car accident and she gives the driver a piece of her mind. She discovers that the driver is a racecar driver and Sonny Mayfield, the owner of the restaurant where she has been hanging out with ""the gang"" that Rachel wants to belong to. When she discovers that they all like him, she works to make herself liked by him, when it appears as though he doesn't like her. Turns out it is just the opposite.

It's Saturday night and Maggie is staying home with her mother, again. Only this time, Mom has a date. Feeling in the way, Maggie goes to Sonny's. Tom suggests that when two older people are alone, they are starving for conversation. Maggie returns, only to find that Mom and her date aren't talking together, they're showering together. Maggie must learn to deal with the fact that her mother has a sex life. Meanwhile, Lisa tries to make it through the killer 3rd date with a guy she really likes, without having sex. Sex she feels will ruin her chance to have a deep meaningful relationship with a man, before she nails him.

Estelle's friends get on Maggie's case because she is in her 30's, single and without children. To prove she can handle those responsibilities she volunteers to watch Robin and Jeff's children while they get away for an evening. With Lisa's ""help,"" Maggie learns what it takes to be a parent, with just a little help from her mother.