The Definite 50 Worst Teen Drama Couples Of All Time

Why they don't work: Dean was an alright boyfriend initially, but he quickly became jealous, controlling, and manipulative. He and Rory had clearly outgrown each other, but they kept revisiting the relationship and making us suffer.

Worst Scene: When they had sex while Dean was still married to Lindsey.

Why they don't work: Dan stalked Serena for years and continuously put her down, then seemed to decide to be with her because he couldn't have Blair. Ew.

Worst Scene: When Serena called Gossip Girl a "love letter" to her.

Why they don't work: Not only was Riley boring, he was seriously jealous and controlling. He acted like a "nice guy" when he was really just awful.

Worst Scene: When Riley left Buffy and dramatically flew off in a fucking HELICOPTER.

Why they don't work: Lindsay was Kirsten's sister, which kind of made her Ryan's AUNT. Also, they probably had the least amount of chemistry out of all of Ryan's relationships.

Worst Scene: When they made out to see "if it was like kissing your sister."

Why they don't work: Felix was super gross and homophobic, and in the beginning he just wanted to get in Brooke's pants. He was such a bad guy and brother.

Worst Scene: When Brooke found out what Felix did to Peyton's locker.

Why they don't work: The relationship was built on cheating, and it felt like it came out of nowhere. It created so much drama in the friend group for no good reason.

Worst Scene: Any time they hooked up while Navid and Adrianna were still together.

Why they don't work: A) They were both way too serious and brooding, and B) they kept betraying Brooke to be together.

Worst Scene: When Lucas told Peyton he wanted more than sex and she was all "why can't you leave it alone?" and stormed off for no reason.

Why they don't work: Volchok led Marissa down a dark downward spiral after she'd already grown so much as a character, and it just felt really unnecessary.

Worst Scene: When he runs Ryan's car off the road in a jealous rage, killing Marissa.

Why they don't work: He was her TEACHER, and he started dating her because he was writing a book about Alison. Enough said.

Worst Scene: When Aria found out about the book.

Why they don't work: Their personalities didn't mesh, and Jughead was obviously not over Betty. Toni even knew they would never work.

Worst Scene: When Toni called her and Jughead's hookup a "PG-13 makeout session." Burn.

Why they don't work: It was kind of understandable that they tried this relationship again, but they simply didn't have enough chemistry. Duncan didn't have any depth, and it was boring to watch.

Worst Scene: When Duncan thought they might be half-siblings (they weren't) and freaked out.

Why they don't work: Peter filmed her best friend Manny topless while she was drunk and sent the video around to the whole school. And then Emma dated him. Um, what the hell?

Worst Scene: When they made out at the movie theater and then saw Emma's stepdad and Peter's mom out on a date.

Why they don't work: Nate seemed more like someone Blair wanted to be with on paper than someone she actually liked. He was no match for her.

Worst Scene: When they kissed in the snow and decided to start dating again for absolutely no reason.

Why they don't work: KAROFSKY BULLIED AND ABUSED KURT. This was never okay.

Worst Scene: When Kurt found out they were dating.

Why they don't work: Guzmán was clearly in love with Nadia and only kept Lu around because she worshipped the ground he walked on. Both characters were much better apart.

Worst Scene: When Guzmán told Lu he cheated on her with Nadia and she slapped him.

Why they don't work: Bryce raped Ani's friend Jessica, along with several other girls. Ani knew about this and just...didn't care? This whole thing was gross and wrong.

Worst Scene: When they slept together. EW.

Why they don't work: LOL. Do we really need to say?

Worst Scene: When Pete was like, "Is it wrong that a hot girl quoting my lyrics turns me on?" PETE, SHE WAS 17.

Why they don't work: They're supposed to be the big romance of the show, but Hope has more chemistry with...uh, pretty much everyone besides Landon. It just feels forced and uninteresting.

Worst Scene: That whole "I loved you when I couldn't remember you" speech. What does that even MEAN?

Why they don't work: PAIGE TRIED TO DROWN HER. Enough said.

Worst Scene: When Paige went behind Emily's back and put Ali in danger by telling the police she was alive.

Why they don't work: Sid had a stupid crush on Michelle despite her being Tony's girlfriend, and Michelle never really wanted to be with him.

Worst Scene: When Cassie caught them together.

Why they don't work: Tristan constantly invalidated Miles' bisexuality and was never called out for it. On top of that, Miles cheated, Tristan never supported Miles through any of his family problems, and they fought constantly. It was just BAD.

Worst Scene: When Tristan said Miles "can't even decide if he likes boys or girls" to humiliate him during the school debate. Honorable mention: When Tristan accused Miles of giving him an STD and slammed him into a wall.

Why they don't work: Becky is literally his dead brother's ex-girlfriend. Absolutely nobody asked for this pairing.

Worst Scene: When they kissed in the middle of a thunderstorm because they saw it as some sort of sign that they're destined to be together. Gross.

Why they don't work: Stefan clearly slept with Katherine because he missed Elena. And Katherine had such a creepy obsession with him from the start.

Worst Scene: When Katherine was in Elena's body and kissed Stefan, taking advantage of his heartbreak.

Why they don't work: Peyton was clearly still into Lucas. Plus, Julian was kind of a dick then and became much better when he dated Brooke.

Worst Scene: When Julian saw her crying and took it as an opportunity to ask her out.

Why they don't work: Jenny seemed too immature for him. They were okay when they dated, but then Jenny schemed and tried to break up him and Serena to get back together with him and it was just creepy.

Worst Scene: When Jenny kissed him while they were playing Assassin for Serena's birthday.

Why they don't work: Adam bullied Eric and made him feel awful about himself. Although Adam has kind of redeemed himself, it doesn't mean it's a good idea for these two to date.

Worst Scene: When Eric told Adam he was the reason it took so long for him to feel secure in his identity.

Why they don't work: HE WAS HER TEACHER. Then they only got together because Caroline was the surrogate for his and Jo's kids.

Worst Scene: When Caroline talked in the car about vampires having wild sex and it was VERY clear she and Alaric were not sexually intimate.

Why they don't work: Amy only seemed to date Ben because she was pregnant and lost. Ben was also super creepy.

Worst Scene: When Amy said she was a whore and Ben said she was his whore.

Why they don't work: They are the antithesis of each other (though both awful people), and they only dated to make people jealous.

Worst Scene: When they showed up to Jenny's party and kissed, then slept together even though Chuck was super sleazy toward her.

Why they don't work: Ani's character as a whole didn't work in Season 3 because she felt like a replacement for Hannah. Pairing her up with Clay felt forced, and it was hard to root for them after everything with Bryce.

Worst Scene: When Ani accused Clay of killing Bryce.

Why they don't work: Monty raped Tyler and no relationship was going to change the monster he was.

Worst Scene: When Monty beat up Winston at that party.

Why they don't work: We all knew Caleb and Hanna were meant to be.

Worst Scene: When Caleb was crying outside Spencer's door and Hanna was listening.

Why they don't work: A) AGE and B) SHE WAS A CON ARTIST WHO PRETENDED TO BE HIS NIECE.

Worst Scene: WHEN THEY HAD SEX. EW.

Why they don't work: It seemed like they just threw them together because Kira had left the show and Stiles had stopped dating Malia.

Worst Scene: When Malia kissed him and it somehow brought back his eyesight?

Why they don't work: Um, they're literal HALF-SIBLINGS. Sorry, too weird.

Worst Scene: When they discreetly hooked up under the family table during dinner.

Why they don't work: Logan was basically only with Hannah to get her dad to clear his name in the Felix murder case, and it was sad to watch her fall for him. Plus, she looked WAY too much like Veronica.

Worst Scene: When they nearly had sex on the couch and Hannah's dad walked in.

Why they don't work: They had absolutely zero chemistry and I'm not sure I believe them having been together. Then he was only with her because he didn't want to endanger Caroline.

Worst Scene: When they talk about constellations and kiss and it's the least romantic thing ever.

Why they don't work: First of all, Dan was a horrible person who felt entitled to Blair because he was "nicer" than Chuck (was he though??). Blair clearly dated him because everything had fallen through with Louis and she was questioning who she was.

Worst Scene: When Blair immediately forgave Dan for leaking the video of her confessing her love for Chuck at her wedding and then showed up at his house to tell him he had her heart, finally referring to him by his first name.

Special note from Kelly: Let the record show that I do not agree with them being on this list, but my co-writer felt very strongly about including them. *Sobs*

Why they don't work: Did we really need to add a fourth person to this love triangle? Lucas was obviously just trying to get over Peyton.

Worst Scene: When Lucas proposed to Lindsey just because she found the ring and was leaving him.

Why they don't work: Mr. Shue was the absolute worst and Emma deserved better. She was so much happier with Carl.

Worst Scene: When Will forced her to rehearse Rocky Horror with him and they got super physical even though she was engaged.

Why they don't work: They totally ditched Hannah to date, and then they didn't seem to have any chemistry. I was perplexed when they dated again — they seemed better as friends.

Worst Scene: When Alex asked her to the dance and she clearly still had feelings for Justin, but she said yes anyway, then cheated on him.

Why they don't work: Honestly, I just really didn't like Anna. They were too similar and Seth was meant to be with Summer.

Worst Scene: When Anna left town and Seth tried to stop her, then she told him they didn't have chemistry and she loved him as a friend.

Why they don't work: They were kind of cute, but honestly their relationship seemed super high school. Then she didn't even tell him when she came back to life.

Worst Scene: When Bonnie was like "I watched you grow up" and basically called him her little brother who got hot, and then Jeremy kissed her.

Why they don't work: Okay, so they were never ACTUALLY together, but they clearly had feelings for each other. He was way too old for her and it was kind of creepy how he always imagined her.

Worst Scene: When he hallucinated her kissing him.

Why they don't work: They were much more like brother and sister than boyfriend and girlfriend, and they never seemed to have chemistry.

Worst Scene: When they had a threesome with Hilary Duff.

Why they don't work: Rachel was only dating him so she could force him to start a TV show that would make them both rich.

Worst Scene: When Rachel forced Dan to have an illegal heart transplant that literally killed a kid.

Why they don't work: It seemed like they only got together because Adrian was pregnant, and that they stayed together because Adrian wanted another baby.

Worst Scene: When they got married in the living room.

Why they don't work: Wren was Melissa's fiancé. Plus, he conspired with Alex when she literally tortured the girls, including Spencer.

Worst Scene: When he gave her a massage while he was engaged to Melissa and she was super turned on.

Why they don't work: Liv never really seemed to like Tyler. She was super rude to him all the time and rarely showed emotion or took responsibility for her actions.

Worst Scene: When Tyler begged her not to go on a suicide mission, so she tricked him by kissing him then knocking him out.

Why they don't work: Fans may have rooted for this pairing in the pilot, but Joey was so clearly better off with Pacey. By the time they actually got together, Dawson didn't seem worth it.

Worst Scene: When Joey rejected him and he had the ugliest cry ever.