Flogging Margaret is a love story about revenge. A year after Keith gets dumped by his college girlfriend it's time to get on with his life. His best friend and constant agitator Chainsaw is the only one in his life willing to kick him hard enough in the butt to get him at of bed and into the real world. They hang out together and even work together as "relationship investigators" catching cheating husband, wives and more, and doing it well. After they run into Keith's old friend Joey, who by the way just came out of the closet, Keith and Chainsaw's eyes are opened into a world of beautiful women, parties, and a couple of German dominatrix named Ursula and Helga. On their first outing together at a night club, Keith meets Chloe, the girl of his dreams. She's fun, beautiful, outgoing, likes the things he likes; she's every man's dream girl. Sparks begin to fly over several rounds of shots and back into the bedroom. Who should show up to ruin this wonderful moment but Margaret, Keith's ex-girlfriend and the bane of Chainsaw's existence. She always wore the pants in the relationship and has a power over Keith that only Chainsaw and a mysterious brown bag can put a stop to.