Definitive Ranking Of Failed "One Tree Hill" Couples

Whether they were actually a thing or just friends, a countdown to the most devastating two-somes that didn’t make it in Tree Hill.

28. Dan & Rachel

CW

This relationship was as short lived as Rachel’s stripping career. Even though she was totally milking him for his new found fame and fortune with Scott Free Redemption, she took it too far by forcing him to film an episode where Jimmy Edwards kills himself. Bad move, Rachel.

27. Karen & Larry Sawyer

CW

Karen and Larry first bonded as chaperones for a Ravens away game in Season 1. The two share a couple of brews, sneak onto the football field to uncover an old time capsule, and bond over being single parents. Although Larry tried, I think this relationship was more of a friendship and would best work platonically. (Plus, just imagine the awkwardness of Lucas and Peyton… gross)

26. Grubbs & Miranda

CW

In case you don't remember, Grubbs was the bearded guru bartender who replaced Chase at Tric, and he started an album at Red Bedroom Records with Miranda (Haley’s awful British assistant). Once Grubbs began producing his album about love lost, Miranda actually started to fall for him. But in true ice queen fashion, she turned down his proposal with her Visa about to expire.

25. Dan & Karen

CW

High school sweethearts always make for a wonderful story. Some play out like a fairy tale: boy meets girl, boy/girl fall in love, get married, have a baby, and live happily ever after. For Karen, news of pregnancy came before marriage (and college), leading to the end of her romantic relationship with Dan (and the fact that he got another girl pregnant and decided to marry her instead could have had a little bit to do with it too). Fortunately for Karen, she totally lucked out raising Lucas on her own (as seen in the episode “What If" in Season 2 after Nathan’s Nascar accident). Although they start to rekindle the flames, once news of her pregnancy breaks, we all know which Scott is really in her heart.

24. David & Quinn

CW

When we first met Quinn, she was already so over David, but I can’t help but think of that cute photo she kept of him wearing a backwards baseball cap behind all the film gear. I imagine that they fell in love hard and fast and just realized that they weren’t meant to be. But when David came back to town with news that he was boffing Quinn’s sister Taylor, he lost all respect.

23. Dan & Deb

CW

These two had turmoil in their marriage from Season 1 episode 1. Between the cheating, lying, and attempted/actual murders, I’m still shocked that they didn’t murder one another. Even though their relationship was nothing but toxic, I couldn’t have been happier when she showed up at his deathbed. RIP DAN :'(

22. Mouth & Shelly/Erica Marsh/GiGi

CW

For a “loser,” Mouth had some good game for getting these three (who I will refer to as the tri-pod from this point on) during his high school career. The tri-pod was there for Mouth’s first M/O, first time, and all had their fair share as members of the Marvin McFadden fan club. Mouth had a way with the quirky, cute, and nerdy girls, but not even the combined power of the tri-pod could ever top a preggo Millicent Huxtable!

21. Lindsey & Lucas

CW

I can’t really entertain the idea of these two for more than a minute or so. Lindsey was the total rebound girl (and she knew it). However, I give her mad props for figuring out the meaning behind The Comet and having the balls to stand his ass up at the alter. Plus, he couldn’t have loved her that much considering he got married to Peyton like 5 minutes later.

20. Peyton & Julian

CW

These two had even less of a chance than Lindsey and Lucas. They only appear as a couple in two or three flashbacks, but Peyton admits they were actually in love. Right. Regardless of this “love” word, Peyton and Lucas have a tendency to throw around with randos. Julian was the rebound guy (and he knew it too). Too bad Julian and Lindsey were never a thing…

19. Mouth & Brooke

CW

Mouth & Brooke were never actually a thing, but Mouth totally wanted them to be. Once he realized his role as the AV geek would never earn him the popular position of head cheerleader, he became an amazing friend to her, even defending her honor and helping her win Student Council President (even though he totally smashed her windshield for getting with Felix). Although Mouth would have done just about anything for Brooke, the relationship would’ve been sad and totally unrealistic (even for TV).

18. Nathan & Peyton

CW

Nathan & Peyton were the token popular high school couple (basketball player + cheerleader = meant to be). Yet the pair (dumb jock + tortured artist) were going in totally different directions (obvious from episode one), plus Nathan was a total dick until he met Haley.

17. Brooke & Felix

CW

Felix was the d-bag, bad boy Brooke always wanted. Totally okay with “friends with benefits,” Felix went from slipping in between her bed sheets to into her heart, and the two became official. They totally had the stereotypical hot guy-hot girl dynamic going on, but once he spray painted DYKE across Peyton’s locker, Brooke decided hoes over bros and kicked his sorry ass to the curb.

16. Lucas & Anna

CW

Anna was the girl from the mall Lucas met on dare night (and ironically Felix’s younger sister). Anna and Lucas had a lot in common – they were both super sensitive, had a thing for Alternative music, and even read the same sad books (however, they also shared a common interest in women). Although these two quit dating, they stayed super close and vented to one another on the daily. Lucas gave Anna the courage to come out, and Anna gave Lucas the confidence to fall for Brooke one last time.

15. Julian & Alex (AKA Alice Whitehead)

CW

Alice Whitehead. I still can’t get over that. Alex was all over Julian like 6th grade crush circa 2005. The girl literally went gaga for him and took it as far as julienning her little chicken arms to prove a point. After coming back to Earth from Planet Crazy, Julian helped her realize her true potential, and the two made the blockbuster hit Seven Dreams ‘Til Tuesday.

14. Skills & Miss Lauren

CW

After it didn’t work out with Bevin or Deb, Skills Taylor moved on to Jamie’s teacher, Miss Lauren (clearly he has a thing for blonde snow bunnies). I absolutely adored that she played teacher while he played coach, and they would totally be good parents together, having multiple beautiful babies. However, Skills made one of the most epic mistakes of a long distance relationship – not asking her to move with him and then stop calling. Although he tried to make it up to her once he returned to Tree Hill, Miss Lauren moved on. Then she got pregnant with Quinn’s ex-husband’s baby. What was Mark Schwahn thinking??

13. Brooke & Owen

CW

Still not sure what Brooke was thinking because Owen was totally smokin’. Although he had that whole recovering heroin addict issue (no biggie), he totally stepped up to the plate when Rachel OD’ed in Brooke’s NYC apartment, and kicked that shady drug dealer’s ass out the door. However, he totally bailed once Brooke wanted to play house with baby Angie because he couldn’t be Daddy Owen, and that was totally not cool.

12. Keith & Jules (AKA Emily Chambers)

CW

After Keith finally finds someone to love (after pining for Karen for nearly 20 years), you find out that their relationship is just too good to be true when Dan hires Emily Chambers as Jules to make Keith fall in love with her just to break his heart as retaliation for sleeping with Deb. In true television fashion, Jules falls in love with Keith, but Dan threatens to reveal their plan, crushing Jules’s plan of happily ever after with Keith. On the day of their wedding (and after a good bitch slap from Karen) Jules flees Tree Hill for good sending Keith spiraling into a depression induced road trip.

11. Skills & Deb

CW

Although this started out as a kinky Internet-sex thing, Skills and Deb totally started to grow on me. The way she was there for him after Quentin died proved that their relationship was more than physical (even if the idea of it made Nathan throw up in his mouth a little bit). Deb always had that Cougar thing going on, but once she realized that Antwon would make a really good father, and she would be holding him back from that opportunity, she decided to be the mature adult and call it quits.

10. Haley & Chris Keller

CW

Although Chris Keller was the epitome of an A-hole, you can’t deny his talent. Chris gave Haley the confidence to sing open-mic at Tric, and launched her career as a musical artist. Even though the two made beautiful music together (their version of "Dancing When The Stars Go Blue" was TDF ) everyone knows that Haley and Nathan are meant to be together.

9. Brooke & Chase

CW

Stephen Colletti playing a virgin wasn’t one of One Tree Hill’s most realistic storylines, but I give casting props for picking him to play super hot Clean Teen Chase. Chase is the first guy Brooke has feelings for after Lucas, and bonus: he makes her want to be a better person. Chase finally reveals he was only interested in being a Clean Teen to avoid having his heart broken, and gives it up to Brooke before senior year comes (LOL) to an end.

8. Lucas & Haley

CW

OK so don’t tell me you never thought these two could be a thing. Although I’m happy they stayed strictly besties, their friendship was everything you would want in a relationship. Friends since they were kids, Lucas and Haley had a bond no one could break (except maybe Chad Michael Murray’s contract demand for more $$$).

7. Mouth & Rachel

CW

Mouth and Rachel were kind of like a Mouth and Brooke thing, except Rachel was somewhat into him and they totally had a weird sexual tension (rando kissing, spending time together during the black out and the motel room in Honey Grove). As a former DUFF (Designated Ugly Fat Friend), Rachel deep down (okay maybe way deep down) had good intentions, but bitchy Rachel ways always found a way to creep in at the worst times (i.e. releasing the time capsule and sleeping with Uncle Cooper). Although Mouth could have loved her whole-heartedly, Rachel could never commit to fully loving him back (And Mouth deserves better than that!)

6. Chase & Mia/Alex

CW

This love triangle tried to be the new Lucas-Brooke-Peyton, but we all know no combination of love affairs could top those three. I always rooted for Chase and Mia until she broke up with him via text (so proper of Season 8’s 2010 airing year). When she tried to get him back I was happy that he stuck with his guns, and the two fist fighting over him during a game of Thanksgiving football game was classic. However, Alex was more than just Chase’s rebound girl, and I thought it was actually sweet that he secretly moved her into his place. Alice, I mean Alex… started running for the hills, and made it to Kentucky-Country where she lived happily ever after as a country artist. WHY CAN’T CHASE JUST BE HAPPY?!

5. Skills & Bevin

CW

When Skills joined the basketball team and met cheerleader Bevin, it was a match made in high school love heaven. After their parents met at a backyard BBQ and were more than okay with the two dating, I thought they were going to make it for the long run, but when she didn't come back to the River Court for Season 5 it was devastating, to say the least. They may not have "officially"made it back together, but I was totally picking up what Mark Schwahn was putting down in the season finale ;).

4. Peyton & Jake

CW

Every girl wishes she had her own Jake Jagielski. Sweet, sensitive, and super cute, Jake had plenty of love to offer. The way they played house was adorable, and the chemistry was there. If Jake’s crazy ex (and baby mama) Nikki wasn’t in the picture and Peyton didn’t sleep talk (I love you Lucas… total plot twist), I think Peyton and Jake could have actually made adorable little siblings for Jenny.

3. Lucas & Brooke

CW

You weren’t a true OTH fan if you didn’t root for this couple at least once, maybe even twice. “I’m the guy for you Brooke Davis” was probably one of the sweetest Lucas Scott lines to hit the CW, and had just about every girl swooning. Their chemistry was totally real, and you know he really loved her (cue breakup/makeup scene in the pouring rain) but Lucas’s love for Peyton (Peyton… it’s you… ugh it gets me everytime) always trumped his attraction to Brooke. In the end, the girl behind the red door wasn’t the girl for Lucas Scott.

2. Clay & Sarah

CW

For barely being viewed as together in the show, the love Clay and Sarah had for one another was one of a kind. Their tragic love story just tugs at the heart strings, and even I think of Sarah when I see purple Kool-Aide. They may not have had an “Always and Forever” type relationship, but they met in college, had one of the most adventurous first kisses I’ve ever seen, and counted to 2 instead of 3 (awww). Too bad she had to collapse on the floor while he talked about pens. What a shame. However, one of the best things about this relationship was that they had a baby together, Logan, before she tragically died. Clays love for her was so deep, that he pushed away the only piece he had left of her.

1. Karen & Keith

CW

This relationship actually broke my heart. 20+ years in the making, Karen and Keith always loved each other even though she was a little late to the game. Keith of course knew it all along, and helped father not one, but two of Karen’s children (when she has that dream of her and Keith playing with their daughter in a field of Lilies, I actually lost it). Before he dies, you see that they truly belonged together, and to be torn apart by something as big as death was completely devastating. Karen & Keith 4 'Eva!!!