Radio talk show host Leon Phelps (Tim Meadows) is a man with a mission. Drawing on his own vast and personal knowledge of love - at least certain aspects of it - he dispenses advice to the men and women of Chicago about matters of the heart - and body. Leon is earnest, inexhaustible and inexplicably attractive to women - he's The Ladies Man - and in his own endearingly innocent way, he only wants to do one thing: help the world with his expert knowledge of amore.
Leon, however, is having trouble finding a new job after he and his producer, Julie (Karyn Parsons), are sacked for the exceedingly "frank" nature of his on-air comments. He is running out of options when he receives a mysterious letter signed only "Sweet Thing" begging him to return to her -- and her money! With enough change, Leon figures, he could buy his own radio station. All he has to do is look in his giant little black book and recall which one of his many sweet things is the "Sweet Thing," but he can't remember. With so many past conquests to sort through, Leon's search promises to be difficult, made all the more complex by a posse of cuckolded husbands determined to take their revenge on him.