Leo and Greenlee find themselves growing more and more fond of each other. Eventually, Leo and Greenlee's attraction turns to love. In the later winter of 2001, Greenlee asks Leo to marry her. Leo fears accepting her proposal because Roger Smythe, Greenlee's father, learned why he originally came to Pine Valley — to swindle Greenlee out of her fortune. As it turns out, Leo developed true feelings for Greenlee and no longer wants her money. He has a prenuptial agreement drawn up that will prevent him from seeing even one cent of Greenlee's money after a split. Roger catches wind of the agreement and flies in a woman from Verona, Italy named Katerina di Courcey. During his days as a con, Leo had taken Katerina for everything she had. Katerina lies and says that Leo asked her for a prenup too. She makes up the story to ruin Leo's happiness, the same way that he ruined hers when he stole her money. Greenlee and Leo promptly split, though it is clear that they both love each other.