The Dirty 30 follows 29 year-old Ricky Simmons (Sean Riggs) whose ex, Lisa, walked out on him with no explanation and broke his heart. Reeling from this crushing blow with no closure, Ricky's best friend Jessy (Giovanni Watson) pressure him to enter the dating world again. He finally agrees to let Jessy play matchmaker and falls for a beautiful woman, only to discover that she is a former escort Kaitlyn (alias Samantha Kimm) played by Nafessa Williams that had been hired by his trusted friend.