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 quickly relearns that she can't remain anonymous in a small town, when she tries to help Tom out with his landlord problem, he can't get his water problem fixed. Her efforts to help Tom, get him evicted and Mr. Stickley, the landlord, also happens to be the representative from the landlord tenant association, amongst his other responsibilities. Meanwhile, Lisa is finding herself attracted to Tom's unkempt, ""skanky different"" look. A solution to Tom's need for an apartment is found above the Winters' garage.