Somewhere in the Midwest in the 1950s, Chad, a hip-swiveling, guitar-playing roustabout, is being released from prison. In a nearby dreary little town a young mechanic named Natalie is dreaming of love and adventure. Natalie is instantly smitten when she meets Chad and she yearns for true love to take her away.
When he finds out about the outlawing of “loud music, public necking, and tight pants" in town, Chad seeks to incite a rebellion. He and Dennis team up to take to the town where Chad meets Sandra, a glamorous museum owner, and falls for her – and he’s not the only one. Natalie’s widowed father Jim also has eyes for Sandra.
With some help from her friend Lorraine, Natalie cleans herself up and rushes off to pursue Chad. Lorraine is given some upsetting news: her beloved, Dean (the mayor’s son), will soon be sent off the military academy. Too in love to bear separation, Lorraine and Dean decide to run away together.
Seeing how taken Chad is with Sandra, Natalie decides the best way to get his attention is to become “one of the guys.” She changes her clothes and alters her voice to become “Ed” and Chad takes him in as his new sidekick. Nothing can go wrong in this scenario, right? In a surprising turn of events, Chad realizes he may have feelings for someone very unlikely, Mayor Matilda finds her softer side, and Dennis and Sandra bond over Shakespeare. Natalie is left alone attending a triple wedding – but, wait, who is that interrupting the ceremony?