As one of the genre-defining teenage dramas of the 2000s, One Tree Hill introduced a new generation of viewers to the concept of the guilty pleasure of rooting for your favorite relationships - and rooting against those you absolutely cannot stand. From the very beginning, the series was driven by love triangles, ones that spanned generations and found children repeating the mistakes of their parents.
But along the way, love stories were told that defied all expectations of teenage dramas and their typical cliches. Couples were formed in the halls of Tree Hill High that managed to survive the unthinkable, ranging from betrayal and cheating to school shootings and unexpected stardom. But there were other couples whose love stories weren't forged in the high school, adults whose romances stood heads and shoulders above the stories of the youngsters they tried their best to help.
At the end of the day, One Tree Hill was a show about love in all its many forms - familial, platonic, and romantic. And at the end of the day, not every love story is one worth rooting for, even if the show thinks it may be.
10 Best: Lucas and Peyton
From the very beginning, it was clear that One Tree Hill's central love story was going to be between troubled artists Lucas Scott and Peyton Sawyer. When the duo first locked eyes in the pilot, something truly special happened; and by the time Lucas was telling Peyton "your art matters; it's what got me here," there was no way that any other relationship could compare - in the show's eyes, at least.
It took a long time for these two to find their way to each other. Bad timing, countless poor romantic decisions, miscommunications, and a seemingly endless string of love triangles kept these two apart. But once they finally, finally made their way back to each other at the start of the sixth season, it was clear that the series would never let them go ever again. At least, until the end of that season, when they drove off into the sunset with their newborn daughter, Sawyer.
9 Worst: Brooke and Julian
Few couples are as poorly matched for each other as designer Brooke Davis and filmmaker Julian Baker. Their existence as a couple at all was likely driven by the fact that Sophia Bush and Austin Nichols were a couple, during those final seasons of One Tree Hill. But beyond that, these two have nothing in common, nothing that works in their favor, and so many things that don't.
It's yet another example of Brooke and Peyton sharing significant others, which is uncomfortable enough. But Julian only came into One Tree Hill in an attempt to win Peyton back - something that Brooke is keenly aware of. And just as she seems to have gotten over that fact, Julian finds himself drawn to another girl again, Alex, even if he claims to not be interested in her. Time and again, these two prove that they're incapable of trusting each other. And yet, they're given one of the show's cheesiest endings of all.
8 Best: Skills and Bevin
The adorable relationship between lovable ditz Bevin Mirskey and loyal friend Antwon "Skills" Taylor was one of the most welcome surprises in the entire series' run. After Bevin chose Skills as her date in the third season's boy draft, the two became virtually inseparable, even spending a date night together watching the beloved romance film The Notebook.
While they were never one of the series' main couples, episodes were always improved by the inclusion of their relationship. And a fourth season episode that touched on their awareness of the fact that their parents may not approve of an interracial relationship - only to totally subvert that plot - was a welcome touch. SO when it was revealed in the fifth season that Skills and Bevin had broken up at some point during the four-year time jump, it was more than a little disappointing. But thankfully, the show finally made things right by having these two reunited in the series finale's flash forward.
7 Worst: Quinn and Clay
Look, we're going to be frank here for a moment: the last three seasons of One Tree Hill just aren't One Tree Hill, at all. Few things can prove that more clearly than the relationship between Nathan's former agent, Clay Evans, and Haley's never once before mentioned sister, Quinn James. Essentially, these two were only introduced as a wannabe Lucas and Peyton, so that Nathan and Haley would have corresponding confidantes and so that there would be a new main couple to care about.
Coupled with the fact that Robert Buckley and Shantel Van Santen are two of the least charismatic actors in the entire series, and share absolutely no chemistry whatsoever, the relationship between these two characters was basically guaranteed to disappoint. It doesn't help matters that Clay shared a far more interesting dynamic with his hallucinations of his deceased wife, Sara, than he ever did with Quinn.
6 Best: Jake and Peyton
Sometimes, the best love stories are the ones that don't get a happily ever after, no matter how much they deserve one. Take, for example, the love story between Peyton Sawyer and Jake Jagielski, which spanned the series' first three seasons and most of their high school years. Troubled teen Peyton and single father Jake took an immediate liking to one another, one that only strengthened with time as they both let their guards down.
By mid season two, Jake was one of Peyton's only true friends, and one of the only people she allowed into her world - and her heart. Together with baby Jenny, the trio had the makings of being a perfect family unit, and likely would have continued being so, if Jenny's absentee mother didn't intervene. The couple got another shot at things at the end of the third season, before Jake convinced Peyton her heart was really with Lucas. But if you ask us, we're still holding out hope for someday.
5 Best: Whitey and Camilla
Sometimes, a love story doesn't need to be seen on screen to be something truly special. Whitey Durham was one of the most beloved characters in all of One Tree Hill, the loyal and compassionate and fiercely protective coach of the Tree Hill Ravens basketball team. His history with the series' central Scott family spanned generations, as did his investment in their lives on and off the court. But beyond his compassionate, teddy bear like demeanor lingered a secret sadness, that he only infrequently discussed.
Camilla was the love of Whitey's life, taken from him far too soon after tragically passing during an unspecified surgery. They had been sweethearts during their adolescent years, and she had always hoped that he would retire from coaching basketball early enough so that they could start a life together for real. Camilla was, according to Whitey, the one thing he could have given it all up for. But after her tragic passing, he continued on coaching, but regularly visited her grave to speak with her.
4 Best: Nathan and Haley
How many times does two teenagers getting married on a whim during high school actually lead to a real happily ever after? Apparently, in One Tree Hill, the answer is one time and one time only. Tutor girl Haley James and basketball star Nathan Scott fell for each other almost immediately when she began tutoring him, and by the end of the first season, they were married.
Over the eight seasons that followed, these two would be put through it all: Haley leaving Nathan to pursue her career in music, Haley returning home and Nathan's resentment of her, renewing their vows to each other, a car accident, an unexpected pregnancy, Nathan's tragic career-ending injury, Haley's return to music, Nathan's miraculous comeback, a crazy stalker nanny, and so very much more. But through it all, they were always and forever by each other's side.
3 Worst: Dan and Rachel
Nothing says true love like a recently released convict, believing he's going to die soon, finding love in a stripper who just so happened to have once dated his own brother, and gone out with his own son. Dan and Rachel's relationship is about as twisted as it gets in One Tree Hill, which is really saying something, considering the level of disturbing things that go on in that small North Carolina town.
When Dan becomes a celebrity author, public speaker, and talk show host, Rachel is right by his side - for appearance's sake, at least. Because behind the scenes, it's clear that this relationship never had any real legs to stand on, beyond Rachel being a gold digger and Dan wanting to have something to fill one of the many voids in his dark, empty life.
2 Best: Keith and Karen
Sometimes, you never do get over your first love, even if you never got a chance to be with them. And sometimes, you finally do get that chance, and everything goes better than expected. Karen Roe and Keith Scott had always loved each other, even though Karen was once romantically involved with Keith's awful brother, Dan. When Karen was raising Lucas all on her own, Keith made sure that he was there for her every step of the way.
"I love you, Karen. I always have," he tells her in the first season. But it takes until the series' third season for these two to finally get their acts together and admit their true feelings for one another. Soon enough, they were engaged, something that Lucas was thrilled to learn. But at the same time, none of this occurred soon enough at all, as Keith was savagely murdered by his own brother, who used a school shooting to disguise the truth. Keith and Karen weren't officially together for very long, and they never got the happy ending they deserved. But Karen gave birth to a daughter, Lily, as a result of their union, ensuring that Keith's legacy would never be forgotten.
1 Worst: Brooke and Lucas
Sometimes, first loves can be a good thing. But other times, they are just so, so bad, and hang around for far too long. Look no further than Tree Hill's resident toxic dumpster fire of a couple, Brooke Davis and Lucas Scott, for the clearest example of that. Brooke and Lucas were ill-suited for one another from the very beginning. Despite knowing that her supposed best friend, Peyton, had feelings for Lucas, Brooke brazenly pursued him, convinced him to engage in behaviors that would get him in trouble, lied to him about being pregnant, and more - and that was all in the first season.
For some reason, the show felt that their relationship, which was only ever based on sexual chemistry and teenage impulses, was one that needed to be revisited time and again, all the way through the fifth season, and even after Chad Michael Murray and Sophia Bush's relationship ended in marriage, and a very public and scandalized divorce. It's hard to find any good that came out of this relationship, really - which makes it all the more impossible to understand why the show clung to it as much as it did.