Haley James and Peyton Sawyer become good friends and each other's regular confidants because they have a common thread connecting them. Unlike Brooke, they didn't have a craze for popularity. Peyton was dating Nathan Scott at that time and Haley was the best friend of Lucas. Nathan and Peyton broke up and Haley started tutoring him and they were attracted to each other. Lucas has feelings for Peyton. Peyton helps out Haley with Nathan and tells her, "You've got his heart, Haley James". Brooke and Peyton drive Haley and that is when between Brooke and Peyton the childhood best friends, enters Haley.
Haley and Peyton's friendship is going from strength to strength. After the wedding of Haley with Nathan, Brooke and Peyton throw Haley a bachelorette party. Haley gets an opportunity to go on a music tour and she leaves Tree Hill and Nathan for the music tour. Due to this, Nathan goes into depression and her newly formed friendship with Brooke and Peyton also suffers. Brooke and Lucas go to visit Haley and are shocked to see her over-friendly behaviour with Chris Keller. Haley refuses to go with them and returns home to an angry Nathan and Peyton
Nathan breaks off his relationship with Haley and demands for an annulment. Peyton remains furious at Haley for leaving Nathan. Everyone close to Peyton had left her and she was angry with Haley for the same. After many tries, Nathan forgives Haley and they sleep together. Peyton also forgives her and says that she was the only one who ever came back. Haley and Nathan renew their vows and Peyton serves as the bridesmaid. Brooke and Peyton fight after the latter confesses to Brooke about her feelings for Lucas
In Season 4 Haley stands up for Peyton to Brooke after she's attacked by Ian Banks. Peyton, Brooke, Rachel and Bevin help Haley when she experiences pain from being stressed. After Haley's accident she stays with Lucas and Peyton decorates her cast and they talk about Lucas. Peyton takes Haley to see Nathan 'dance' for money.
In Season 5 Haley is struggling with Nathan after his accident and Peyton helps her out by taking Nathan to the hospital and giving her a piece of her mind. Haley discovers Mia Catalano and tells Peyton to sign just her. Peyton signs Haley as an artist for Red Bedroom Records. Haley tells Lucas not to marry Lindsey because she thinks he is still in love with Peyton. After Lucas told Peyton that he hated her she was throwing water balloons off the roof of clothes over bro's and Haley came to consult her.
In Season 6 Haley preforms on the USO show for Peyton. Haley gives Peyton advise about her pregnancy and she helps Peyton after she's been put on bedrest by helping Mia Catalano with her music. Haley and Mia bring the studio to Peyton and Mia preforms a song for her. Haley gives Peyton a memory book for her baby shower. Haley is the minister at Peyton and Lucas' wedding. Haley comes to visit Peyton in the hospital after she wakes up after giving birth to Sawyer.
In Season 7 after Peyton and Lucas have departed from Tree Hill Haley takes over Red Bedroom Records.
- Both Haley and Peyton share a common love for music.
- Haley and Peyton share a very special relationship with the Scott brothers, not necessarily romantic.
- Haley and Peyton are connected by three relationships; They are best friends, they are sisters-in-law and they have been colleagues.
- Haley's sisters, Quinn James and Taylor James call her Haley Bob, also using her middle name. Peyton's best friend, Brooke called her Peyton Elizabeth Sawyer.
- After Lucas got engaged to Lindsey, she said there would be two Mrs Scotts; Haley Scott née Haley James and Lindsey Scott née Lindsey Strauss. But Peyton became the second Mrs Scott.
- Haley and Peyton consider Brooke as their best friend.
- Peyton's daughter, Sawyer Brooke Scott's godmother Brooke is also godmother to Haley's son, James Lucas Scott
- James Lucas Scott and Sawyer Brooke Scott have the middle names Lucas and Brooke.