Dennis Loggins is a young multi-billionaire. He’s become a success, he’s gotten in shape, he’s spent years improving himself, and he’s done it all for the love of a good woman. Or so he tells himself. The fact is that Dennis has engineered this façade of confidence and importance solely as a means for revenge. In high school Dennis was a nerd with a crush on the head cheerleader, Melissa. Due to her kindness and attention, Dennis’s crush transformed into unrequited love. To make matters worse, he was constantly tormented and humiliated by Ricky, Melissa’s boyfriend.

On one memorable occasion, Ricky tricked Dennis into admitting his love for Melissa over a live microphone at the football game. Dennis never got over the humiliation, despite Melissa’s assurance that he needn’t worry. Now years later, Dennis is a success, and is eager to return Ricky’s slights ten-fold. He hires Gloria on as an assistant specifically to find out what football team Ricky is playing for, and to help Dennis re-plan the ten-year high school reunion. Moving the gathering to a much more glamorous location, and bringing Gloria as his “date”, Dennis waits eagerly for the payoff of his plans. He has bought the football team that Ricky plays for, and has arranged for a phone call to be made a minute before the crowning of the King and Queen of the reunion, to tell Ricky that he’s fired. When Ricky arrives, it’s obvious that he’s changed. He apologizes to Dennis for the grief he gave him in high school, and congratulates him on his success. Ricky is nonplussed, but is so wrapped up in the pending arrival of Melissa, that he all but ignores the change.

When Melissa shows up it’s more than obvious that she too is different. She’s dying of cancer. Dennis is blown away, he stands with his jaw hanging open as Ricky hurries to Melissa’s side and lovingly leads her through the gathering. Dennis goes over to her and they talk for a while, she tells him how her illness has changed Ricky into a warm, caring, compassionate man. Dennis instantly regrets his plotting and scheming, and hurries inside to swipe Ricky’s cell phone, before the call arrives. He makes it just in time, and Melissa and Ricky take the stage as King and Queen of the reunion. Toby Keith hired by Dennis as part of the night’s festivities takes the stage to perform “My List”.