Breakups and makeups were a staple to storylines on One Tree Hill, much like other teen dramas. From complicated love triangles to high school marriages to everything in between, it was a miracle if a couple lasted an entire season without any relationship drama.
Some breakups in Tree Hill hurt a lot more than others. Deb and Dan's marriage ending in the first season was predictable and a long time coming, given that the pair seemed unhappy from the minute they appeared together on-screen. However, Nathan and Haley's season 2 breakup hurt the show to the point where it is regarded as one of the worst seasons, and every time Lucas Scott broke Brooke Davis' heart, fans' hearts shattered too.
8 Keith & Jules (Season 2)
Keith and Jules met at the car dealership while Keith took over for Dan following his first heart attack. Unbeknownst to Keith, Jules was hired by Dan to seduce and fall in love with him, only to leave him heartbroken and alone.
The plan orchestrated by Dan worked, and Jules abandoned Keith on their wedding day. However, one thing Dan did not foresee was the two of them actually falling in love, and Jules being just as hurt over the ending of their relationship as Keith was. The two attempted to make it work once he learned of her real identity, but ultimately it failed due to the lies their romance was based on. It was heartbreaking to watch unfold nevertheless because Keith so badly wanted and deserved true love and happiness.
7 Brooke & Lucas (Season 1)
Brooke and Lucas broke up for the first time following his car accident in season one. He realized upon arriving home that he actually wanted to pursue a relationship with Peyton, and that he and Brooke were never going to work out long-term. This shocked Brooke, who had no idea he was having any doubts or hooking up with her best friend behind her back.
Their initial breakup and the way Lucas let Brooke down were pretty typical as far as high school relationships go, but it was the aftermath that made this split so painful. When Brooke discovered the reason that Lucas dumped her, and her best friend's involvement, she felt completely betrayed and like she had lost the two most important people in her life at once.
6 Peyton & Lucas (Season 5)
Fans waited four seasons for Lucas and Peyton to finally get together and start a real relationship and when they finally did, it was over as soon as season 5 premiered.
The time jump revealed that Lucas was engaged to someone completely new, his editor Lindsey. Meanwhile, Peyton was still pining over him upon her return to Tree Hill and was desperate to break up their wedding. Fans didn't get to see the Leyton breakup at first, but flashbacks revealed that when Peyton rejected his initial marriage proposal, Lucas dumped her. It was sad to watch such a quick downfall of a long-awaited romance, but thankfully the two found their way back to one another before the season was over.
5 Mouth & Millie (Season 7)
Mouth and Brooke's assistant/co-worker Millie were the sweetest couple on the show, but they were not exempt from their own relationship trials and tribulations. Though they seemed like the perfect match, communication issues and career changes led to their brief yet devastating demise.
In season 7 Millie started modeling for Brooke's company 'Clothes Over Bros' and quickly got wrapped up in a lifestyle much different than what she was used to. She started using drugs and drinking too much, eventually getting arrested. She and Mouth went their separate ways and he began talking to Jamie's teacher, causing Millie to be completely heartbroken. Luckily they were able to work things out, but their time apart made both their characters sad and unlike their usual selves.
4 Brooke & Julian (Season 7)
Brooke and Julian technically split up twice. The first time when they began dating and she got cold feet when he confessed his love for her, and the second time after a dramatic love triangle between her, Julian, and actress Alex Dupre.
When Julian got closer and closer to Alex, Brooke was disappointed and expressed her negative feelings about their relationship. However, Julian refused to listen or take her concerns seriously and saw himself as helping a friend in need. Alex of course had some ulterior motives and wanted Julian for herself, but was also going through a lot of personal struggles. When Julian rushed to be by her side instead of Brooke's, Brooke ended their relationship, and fans were crushed at the thought of Brooke losing her one true love forever.
3 Peyton & Jake (Season 3)
Jake was Peyton's second-best love interest on One Tree Hill. He was kindhearted, devoted and a great father to his baby girl Jenny. He and Peyton had a great connection that was constantly broken up by the impending doom of Jenny's mother, but they continuously found their way back to one another.
However, the two just couldn't make it work long-term. Their relationship ultimately came to an end when Peyton whispered Lucas's name in her sleep while with Jake. He realized that he was never going to be her Lucas Scott. This left viewers and Peyton heartbroken, as Jake Jagielski deserved the world, and in another life, he and Peyton would've made an amazing couple and parents to Jenny.
2 Haley & Nathan (Season 2)
Nathan and Haley famously got married in their junior year of high school at the end of One Tree Hill's first season but started having marriage troubles almost immediately at the start of the second.
Things started to get rocky when Haley pursued her music career and chose to go on tour with Chris Keller instead of staying in Tree Hill with her husband. Nathan felt betrayed and alone and filed to annul their marriage. The pair remained split up for most of the season to the dismay of viewers, as they were previously the most solid and healthy relationship on the show. It brought the show down and made both their characters worse, so it is a good thing the writers got them back together in season 3.
1 Brooke & Lucas (Season 3)
Brooke and Lucas tried another go at their relationship in the third season of the show, only for things to end much like they did the first time. Lucas was still hung up and in love with Brooke's best friend, and Brooke was trying desperately to get him to see her the way she saw him.
Their breakup at Nathan and Haley's vow renewal was particularly painful due to Brooke's pleading with him to need her the way she needed him. He couldn't do it though, and Brooke had enough self-respect for herself to end their relationship. Her speech to him on the dance floor was peak acting by Sophia Bush and broke the hearts of just about everyone watching.
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