Life in the small town of Grandview, Illinois is one that is just like any other city or town. Tim Pearson, soon to be graduating high school wants to go to Florida to study oceanography. He meets Michelle "Mike" Cody and is attracted to her. She runs the local Demolition Derby place. Ernie "Slam" Webster is one of the drivers in the derby who's wife is cheating on him and wants to later on be with Mike. Tim falls for Mike and a big love triangle is about to happen.
Naive Midwestern prep student Jonathan bonds with his more worldly roommate, Skip, who takes the small-town boy under his wing. At Skip's urging, the inexperienced Jonathan is emboldened to seek out older women in the cocktail lounges of nearby Chicago, where he meets and beds the alluring Ellen, who unfortunately turns out to be Skip's mother. The division between the friends is further deepened when a cheating scandal engulfs the school.
Tess McGill is an ambitious secretary with a unique approach for climbing the ladder to success. When her classy, but villainous boss breaks a leg skiing, Tess takes over her office, her apartment and even her wardrobe. She creates a deal with a handsome investment banker that will either take her to the top, or finish her off for good.
When record store owner Rob Gordon gets dumped by his girlfriend, Laura, because he hasn't changed since they met, he revisits his top five breakups of all time in an attempt to figure out what went wrong. As Rob seeks out his former lovers to find out why they left, he keeps up his efforts to win Laura back.
Art Dodge is a painter-turned-gallerist drowning in debt. He gets in over his head when a con job leads to an engagement with a rich divorcee. He gets in deeper when he falls for her sister, and invents a twin brother to be her beau; and deeper still when his fiancée's ex-husband comes looking for revenge.
Novalee Nation is a 17-year-old Tennessee transient who has to grow up in a hurry when she's left pregnant and abandoned by her boyfriend on a roadside, and takes refuge in the friendly aisles of Wal-Mart. Eventually, some eccentric but kindly strangers 'adopt' Novalee and her infant daughter, helping them buck the odds and build a new life.