During their first two years of high school, Nathan, the basketball star, entered a romance with the lonely cheerleader, Peyton Sawyer. They mostly had sex during their relationship. Peyton broke up with Nathan early in season 1 in the episode Crash Into You.
Nathan and Peyton broke up in Crash Into You and never got back together after that, but stay great friends.
- After Nathan and Peyton's break up the pair became good friends. They often reminisce about their relationship and Nathan often said that they were good together. Peyton would always counter this by saying that they were horrible together or that they just had a lot of sex. Nathan would then agree with her and the pair would laugh about it.
- Peyton broke her knuckle once because she punched a wall in anger after one of her and Nathan's many break ups.
- During the summer after Nathan and Peyton first got together Nathan went to the weights room of Tree Hill High every day to lift weights and everytime he benched 10 pounds more he carved Peyton's initials "PS" into the bench press.
- Peyton said that Nathan was good in bed.
- Peyton lost her virginity to Nathan.