Dan started to date one of the multiple James sisters; Quinn James while in her freshman year at Tree Hill High and she developed feelings for him. He broke up with Quinn because Taylor; Quinn's older sister said to him that if he was to break up with her she would have sex with him. So he did and broke up with Quinn and had sex with Taylor in Lydia James's car while which Taylor blamed on Quinn. This added to the problems of their relationship with the affiar being a strong issue between the two sisters. ("Weeks Go By Like Days")
Quinn James (girlfriend)
- Start up: before the Pilot. (during freshman year of Quinn)
- Break up: before the Pilot (during freshman year of Quinn)
- Reason: Taylor said to him if he break up with Quinn she will sex with him. So he break up with Quinn and he have sex with Taylor.
Taylor James (one-night-stand)
- Start up : before the pilot and after he break up with Quinn.
- Break up: before the pilot
- Reason: It was just a one-night-stand.
- Like Quinn's husband David Fletcher he 'dated' with both Quinn and Taylor James.