Lovesick is the comic tale of Charlie Darby (Matt LeBlanc), a man who has everything going for him: a great job as an elementary school principal, supportive friends and a wonderful life. The one thing that Charlie doesn't have is love because every time he starts to fall for a girl, his brain chemistry changes and he goes clinically insane. When he meets Molly Kingston (Ali Larter), a former dancer who just might be his perfect match, Charlie is confronted with the consequences of his condition. With the help of his friend Jason (Adam Rodriguez) and the often misguided advice from his wacky neighbor Lester (Chevy Chase), Charlie must find a way to overcome his psychosis to claim his chance at true love.

Tripp is an average frustrated chump, who comes up with a golden idea. He partners with Gary, a Wall Street wheeler and dealer, and brings his cousin, Rowan, on-board to help with his business. As Tripp and Rowan journey together for business, Tripp learns about Rowan's extraordinary skills- skills in attracting women. The duo realizes that business and relationships today have a lot in common. Tripp learns Rowan's game and begins closing on business deals. But the problem is, Tripp is married. As the business grows to be worth millions, Tripp realizes that there are many players around him who want a piece of the gold. He must decide to either fight for the gold, or find love, with his new found knowledge of the game.