They never are friends and hate each other. When Damien came to Tree Hill for a game against the Ravens he tried to charm Haley, Nathan's wife. Dan and Nathan convince him to stop. Damien thinks that they are going to win the basketball game against the Ravens but the Ravens are too strong, particulary Nathan. Damien wants to take Nathan in 1 on 1 in defense and finally lose when Nathan score the winning's shoot in free throw after a foul of Damien.