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The following are the details of the relationships that Nathan Scott has been a part of throughout and before the series.


Haley James Scott
Start Up: The Search for Something More
Marriage: The Games That Play Us

Relationship: Wife and Love of his Life
Details: During their first two years in high school, Haley and Nathan were estranged and opposites: Haley enjoyed school and tutoring, whereas Nathan enjoyed basketball and failed several classes, she was a mature and kind girl while he was an irresponsible and immature guy. After the addition of Lucas on the Ravens basketball team at the beginning of junior year, Nathan asked Haley to be his tutor: originally a tactic to make Lucas want to leave the team, he grew closer to Haley, getting to know her, and then quickly developed feelings for her. The two soon started a relationship, which became so important that they decided to get married in the middle of their junior year of high school and also waited to have sex for the time until their wedding night because Haley wanted to. In season 4, Haley discovered she was pregnant with their first child and, at the graduation ceremony, during her valedictorian speech, she went into labor and then gave birth to the baby, whom the two called James Lucas Scott. Then, many years later, Nathan and Haley also had a daughter, Lydia Bob Scott. The couple also faced many struggles, like a distant relationship when Haley developed a crush for the musician Chris Keller and went off on a music tour with him not long after they got married, which nearly brought their relationship to an end, but after her return they succeeded in making things work and they also decided to renew their vows at the end of season 3. Similarly, their child's nanny, Carrie, caused trouble by flirting with Nathan, who, at the same time, had become insuffurable because of getting an injury at his back which nearly prevented him to play basketball anymore, and also other problems came around when a woman claimed to be carrying Nathan's child saying she slept with him during a drunken party night, but in the end, this allegation was proven to be false and, finally, Nathan being kidnapped, causing Haley to have to track him down. Anyway, the couple managed to stick together during thick and thin, following their personal dreams successfully and still proving to have a very happy and healthy marriage.
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Taylor James
Start Up: Before Pilot

Relationship: One-Night-Stand
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.
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Peyton Sawyer
Start Up: Before Pilot
Break Up: Crash Into You
Relationship: Ex-Girlfriend
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.
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Brooke Davis
Start Up: Before Pilot

Relationship: One-Night-Stand
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.
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Rachel Gatina
Start Up: Things I Forgot at Birth
Ended: I Love You But I've Chosen Darkness

Relationship: One-Sided Attraction by Rachel, never reciprocated by Nathan
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.
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Carrie
Start Up: Don't Dream It's Over
Ended: Running To Stand Still

Relationship: Attraction
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.
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