Details: Nathan met Taylor at a basketball party at his parents beach house during his freshman year. The two got very drunk and hooked up for one night and he lost his virginity to her. He never even knew her name at the time. It was quite a shock when he met her again his junior year and she turned out to be his new sister-in-law.
Details: During their first two years of high school, Nathan, the basketball star, entered a romance with the lonely cheerleader, Peyton Sawyer. They had a very argumentative relationship that often had them breaking up and then reuniting with each other several times each week. Nathan showed little interest in Peyton and only her liked for sex. Eventually, Peyton had enough of Nathan and his behavior and ended their relationship.
Details: At a party at Nathan's beach house, Peyton and Nathan were involved in yet another argument. Peyton eventually has enough when he sees Nathan flirting with another girl and breaks their relationship off. As Nathan laughs the situation off, Peyton assures him that they will not be getting back together. That night, Nathan gets really drunk, and as usual, so does Brooke. Brooke finds out him and Peyton have broken up, and they decide to hook up. As they go upstairs and undress, Nathan gets a video camera out and they make a sex tape. Although reluctant at first, Brooke is persuaded by Nathan who promises no one will ever see it. The following morning, the two decide to keep it a secret when Peyton and Nathan get back together again.
Details: During their years in high school, Haley and Nathan were always opposites. Haley enjoyed school and tutoring, whereas Nathan enjoyed basketball and failed several classes. With the addition of Lucas Scott on the Ravens basketball team, Nathan asked Haley to be his tutor. Originally a tactic to make Lucas want to leave the team, he grew closer to Haley and developed feelings for her overtime. They were married in the middle of their junior year of high school and waited to have sex until their wedding night. At graduation, during Haley's valedictorian speech, she went into labor and gave birth to their first child, James Lucas Scott who was followed years later by a daughter Lydia Bob Scott. The couple have also faced many struggles. They faced a distant relationship when Haley went off on a music tour not long after they got married, which nearly brought their relationship to an end. Similarly their child's nanny, Carrie, caused trouble by flirting with Nathan, and also when another woman claimed to be carrying Nathan's child and that he slept with her during a drunken party night, but in the end, this allegation was proven to be false. And Nathan being kidnapped causing Haley to have to track him down. The couple have managed to stick together during thick and thin, following their separate dreams successfully and still prove to be the happy couple that is Naley.
Details: After the car accident and Cooper's departure from Tree Hill, Rachel turned her interests to Nathan (possibly as a consequence of her unresolved feelings for Cooper as she explicitly stated that Nathan had Cooper's eyes). Rachel flirted with Nathan and used the car accident to get close to him, even going as far as lying about seeing Keith under the water to give them a connection that would have Nathan interested as well. Rachel clashed with Haley over her flirtation with Nathan, but she soon backed off when it was revealed that Haley was pregnant. Nathan would later tell her she never stood a chance, even if Haley hadn't been pregnant.
Details: When Carrie was hired as a nanny for Jamie by Haley, the family got more than they bargained for. Carrie decided she wanted to replace Haley in their family entirely. She began making moves on Nathan and even pretended that Jamie was her son. Carrie flirted with Nathan by swimming in the pool naked whilst he watched, and even getting in the shower with him. Haley eventually found out, and Nathan and Haley seemed unlikely to rekindle their relationship, but Nathan truthfully convinced her that he did not initiate anything with Carrie, and he was forgiven.