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")
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