Once Leo leaves Laura, Greenlee becomes torn between Jake and Leo. Neither man wants to be "the other man." Leo proposes to Greenlee and she accepts, but the engagement is later broken when Leo tries to give her the ring in front of Jake and Laura, which Greenlee takes as an attempt to show up Jake. The two quickly get back together however, but the happiness is short-lived. Greenlee ends up trapped on an island with Jake after she is drugged and left for dead on a sinking boat by Leo's mother, Vanessa Cortlandt, who sets it up to make Leo think Greenlee has left him for Jake. Greenlee and an also-drugged Jake escaped their near-watery grave, but Greenlee's unwillingness to commit to Jake results in Jake walking away and Leo and Greenlee happily reunite.