After receiving the employee of the month award, after three weeks of work, Maggie gives in to Rachel's invitation to join her family for dinner that evening. Leaving, Robin, Lisa, Jeff and Tom to be entertained playing a game with Estelle. Rachel's family turns out to be just as bizarre as she is, but Maggie endures the evening and tries to make Rachel shine in the eyes of her family, unfortunately, they only see Maggie.

Maggie wants to surprise her mother by having her father join them at Thanksgiving. When she realizes her mother would rather never see him again. So she checks her father into a motel under an assumed name, but word gets out the Maggie Winters is seeing an old man at a sleazy motel, her mother is beside herself. On Thanksgiving Day, Maggie reveals who the old man in her life is; now Estelle is really beside herself.

Maggie runs into the high school teacher (Mr. Wiehe) that she, Lisa and Robin had a crush on. She gets an invitation to come to a school play, which leads to a date. Even though Maggie wants the date to be solo, Lisa and Robin tag along. Mr. Wiehe, was the only teacher to ever give Maggie a grade of B, so she feels that each time he gives something a rating, he is actually grading. She works hard to try and get a grade of A.

When Lisa changes to continue dating a Harvard educated man, Robin and Maggie are taken aback. Robin suggests that Maggie, as the bossy one, must do something about it. Meanwhile, Estelle is taking a dream analysis course and she analyzes one of Tom's dreams. She believes he is denying the exploration of his feminine side. When Maggie confronts Lisa, Lisa only becomes angered and they break apart. Robin brings Maggie and Lisa back together, especially when Lance makes a move on Robin.

Maggie is introduced to the concept of single's night at the grocery store, you get a 10% discount and maybe a date. Of course, Maggie still has to confront the task of signing her divorce papers. Maggie tries the dating scene at the grocery store; however, Sonny tells her that now she needs to go on a real date. He offers to have one with her, even though he doesn't really like her. Their date reveals things about their respective relationships, but in the end Maggie accomplishes one of her tasks.

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.

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.

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.

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 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.