Most Likely To Succeed - S8.E7

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 facade 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 hel