Schemers Leo du Pres and Greenlee Smythe meet when Greenlee is trying to win back college flame Scott Chandler from virgin do-gooder Becca Tyree. Leo wants Becca for himself, so when Greenlee offers him a bet to get Becca into bed, Leo readily takes the challenge. Leo and Greenlee's friendship deepens and as time passes, they learn they have a lot in common. Greenlee eventually moves on to attempting to seduce Ryan Lavery, but gives him up when it becomes obvious that he only loves Gillian Andrassy. Greenlee develops a relationship with Leo. The two fool around, but neither think about becoming a serious couple.