Top 20 Devastating Breakups on Disney Channel Shows

#20: Robbie & Wendy

“Gravity Falls” (2012-16)

Wendy hasn’t had the best luck when it’s come to relationships, and her romance with Robbie is no different. In “Boyz Crazy” it's at its lowest point. That’s because she learns that a song Robbie wrote for her was actually stolen from another band. Not only that, the song was secretly mind-controlling her. That’s right, he mind-controls his girlfriend, it’s wild. Unsurprisingly Wendy eventually dumps him. It’s a rough breakup because not only was the song dangerous, it was also someone else’s, making Robbie a liar. Though Wendy’s justified for calling it quits, she's pretty heartbroken afterwards. She even lashes out at Dipper when he immediately tries exploiting the situation to get to spend more time with her. Yeah, read the room, Dipper, not cool!

#19: Ren & Bobby

“Even Stevens” (2000-03)

There’s a saying that candles which burn twice as bright also burn half as long, and that same idea can apply to romances. Ren cared about her boyfriend Bobby, but things broke down in the episode “Sibling Rivalry”. When Ren and her brother Louis bicker endlessly, the two are motivated to go on a tv program to squash their beef. However, the game show’s unethical rules require them to humiliate each other. To make a long story short, Louis gains video evidence of Bobby with another girl. Ren eventually confronts him and they split, but the damage is done. Getting cheated on is brutal, and if Louis hadn’t changed his mind, her pain would’ve been broadcast as part of the game show’s insensitive shenanigans. Ouch!

#18: Olive & Fletcher

“A.N.T. Farm” (2011-14)

Everybody knew that Fletcher was head-over-heels in love with the character Chyna Parks, so him dating her friend Olive instead was surprising. They were actually a cool couple, but their relationship didn’t last forever. In “the new york experiANTS”, Fletcher gets a lucrative educational opportunity to pursue art. But since it’s in New York, that complicates things. Olive brutally breaks up with him on the spot and Fletcher is caught off guard. It’s later revealed though that she did it so Fletcher wouldn’t give up the art opportunity. Olive had understandable intentions but it didn’t make the breakup any less sad. Plus, this happened in the series finale, which made things go from sad to downright depressing. They seriously couldn’t give long-distance a shot?!?

#17: Jackie & Marco

“Star vs. the Forces of Evil” (2015-19)

Though many fans knew that Star and Marco were the endgame it was still nice to see Marco's relationship with Jackie take form. They were great together and the pairing seemed all set for happiness, until their relationship hit a setback. Jackie knew that ultimately Marco still missed Mewni: a magical world he spent some time living on. Jackie decides to call the relationship off, and while it’s a mature and respectful split we can tell that Marco is deeply affected by it. Jackie was his first major love and someone he had feelings for since they were kids. So as you could imagine, losing her would hurt. Long-distance relationships are tricky as is, but an inter-planetary romance is next to impossible to pull off.

#16: Lucas & Maya

“Girl Meets World” (2014-17)

Love triangles are all the rage apparently, and when it comes to “Girl Meets World”, there was a big one revolving around Riley, Lucas, and Maya. The show built up Lucas and Riley as the big potential couple, but eventually Lucas and Maya had something going on. While they had chemistry and feelings for each other, Maya realized her feelings weren’t of romance. Instead they were of friendship. This led to her breaking up with Lucas and urging him to pursue a relationship with Riley. They still remained good friends afterwards, but many fans who liked this pairing felt thrown off by the breakup. In fact, this particular situation is really interesting because you could argue that fans were more devastated than the characters themselves!

#15: Jessie & Brooks

“Jessie” (2011-15)

Weddings have happened lots of times on Disney Channel, but not all weddings have gone down smoothly. If you want one example of an epic wedding trainwreck look no further than Jessie’s. She was supposed to marry Brooks, but he was eventually going to have to leave for Africa because of work. Jessie couldn’t handle the idea of leaving the kids she nannies for behind and that became a major fork in the road. Ultimately the couple wanted different things and the marriage broke down. What makes things worse is that their breakup happened on their actual wedding day which is supposed to be the happiest day of their lives! This isn’t simply devastating, there’s a chance this experience was legitimately traumatizing.

#14: Miley & Jake

“Hannah Montana” (2006-11)

Jake Ryan was set up to be a pretty big deal on “Hannah Montana”. Not only was he in a serious relationship with Miley, but he was even considered to be “the one”. That’s right, this show did a whole double-length special basically telling you that he was Miley’s soulmate! But guess what happened, he ended up cheating on her! Yeah, that’s a screwup of epic proportions. Not surprisingly Miley dumped him afterwards once she found out that he was a no-good cheater. Jake’s reckless decision was a pretty epic blunder on his part and he exited the show looking like a fool. Miley originally chose him over Jesse, but we bet she regretted that decision!

#13: Jake & Rose

“American Dragon: Jake Long” (2005-07)

Dragon-slayers and dragons are bitter rivals but Jake Long and Rose Thorn fell in love anyways. However, a lot kept them apart. In “Homecoming”, the leader of Rose’s hunting clan (the Huntsman) plans to use Aztec wish-granting skulls in order to destroy all magical creatures. Rose stops him and wishes for the clan to be destroyed, unfortunately, this means she’d also get destroyed. To save her, Jake wishes that she never became a hunter. Though she’s still taken, we learn that Jake’s wish worked. However, it wipes her memories and she forgets him, essentially ending their relationship. This wasn’t their first breakup, but it’s the one that arguably hit the hardest. Jake made a difficult decision that paid off yet still cost him dearly.

#12: PJ & Skyler

“Good Luck Charlie” (2010-14)

Skyler was treated pretty poorly early on in this show. Her boyfriend Spencer was actually a cheater, which led to her (and Spencer’s other girlfriend Teddy Duncan) getting heartbroken. Thankfully though she and Teddy became friends and Skyler later found love again when she started dating Teddy’s brother PJ. The quirky goofballs were an instantly iconic couple who gelled insanely well together. But when Skyler had to leave for New York, she broke up with PJ. The breakup was actually played for laughs, but while it definitely had some humorous moments, it was clearly a brutal experience for poor PJ. Hey Disney Channel, why don’t you show the man some respect while he’s grieving and not make him a punchline! You’re on thin ice now.

#11: Justin Russo & Juliet Van Heusen

“Wizards of Waverly Place” (2007-12)

Justin Russo has had it rough when it comes to romance. Sure, he eventually settled down and started a family in “Wizards Beyond Waverly Place”. But back in the OG days he was fumbling his way through his love life. He was infatuated with his vampire girlfriend Juliet, but vampire romances don’t always do so well. He also dated an angel named Rosie, which sadly didn’t pan out either. Anyways, when Juliet and Justin got trapped in a museum, the only way out before morning time was for Juliet to get taken by the evil mummy Justin was hunting. Yeah…this show got wild. Justin was crushed when he lost her, and though they found each other again later, things were never quite the same.

#10: Andi & Jonah

“Andi Mack” (2017-19)

For a long time it seemed that these two would never like each other at the same time. So when they finally did get together, all Jandi shippers rejoiced. Unfortunately, that joy was short lived because Jonah left for two weeks of frisbee camp, and when he returned things were just not the same. Though their romantic relationship had felt like the be all and end all to both, they realized that they were better off as friends. Actually, we might have to classify this one as an un-breakup. The scene is emblematic of the confusing feelings that come with being a teenager. And though, ultimately, they were better than ever, this one still makes us sad. We were rooting for those two crazy kids.

#9: Zack Martin & Maya Elizabeth Bennett

“The Suite Life on Deck” (2008-11)

Zack had a reputation for being a ladies man, but when Maya came aboard he gave her all of his attention, feeling that she could be the real deal. It took him a while to gain her trust, but Zack amazed everyone with how good a boyfriend he was. Unfortunately, Zack got his heart broken when Maya joined the Peace Corps after graduation. Zack was dedicated to making long distance work, but Maya wasn’t too into the idea. Though she tried to be as gentle as possible, Zack - usually the cool twin - was still heartbroken. It was hard to see him so hurt.

#8: Lizzie & Ronnie

“Lizzie McGuire” (2001-04)

Lizzie's paperboy, Ronnie, was her first boyfriend, and he broke her heart. Lizzie was totally smitten with this guy. So much so that she effectively isolated her friends with just how disgustingly annoying they were together. And just as quickly as it started, Ronnie ended it brutally. He broke up with her for another girl that went to his school because she was, quote, "right there and everything". What a tool. We’ve seen Lizzie through some tough times, but this one was a real blow. Watching her cry her eyes out over that loser was heartbreaking. Thankfully her friends were still there to pick up the pieces.

#7: Chad Dylan Cooper & Sonny Munroe

“Sonny With a Chance” (2009-11)

A healthy dose of friendly competition has always been a huge part of the Channy relationship. But things escalate to a whole other level when both of their TV shows are up for a Tween Choice Award. Both casts get a little insane about the whole thing, but Chad in particular becomes very obnoxious in his confidence that he’ll win. After apparently losing, Chad can’t take it and demands a recount. It turns out his show won after all, but it makes Sonny realize that he’ll always put himself above everything and everyone else. She can't be with someone who has that little respect for her and breaks up with him. At least Chad has his award to keep him company.

#6: Cody Martin & Bailey Marie Pickett

“The Suite Life on Deck” (2008-11)

This is a bit of a weird one, because the catalyst for Cody and Bailey ending their relationship was a huge, ridiculous misunderstanding. Cody was so nervous about making his anniversary with Bailey perfect that he recruited London’s help; but Bailey misread the situation and thought Cody was cheating. Then, when Cody saw another guy hugging an upset Bailey, he assumed that SHE was cheating. The whole mixed up situation culminated in a huge argument on top of the Eiffel Tower. The way they attacked each other was brutal - and it’s so disappointing that after a year together they were quick to assume the worst about each other.

#5: Liv Rooney & Holden Dippledorf

“Liv and Maddie” (2013-17)

What makes this one so devastating is that they both still really cared about each other. Holden just couldn't deal with always coming second to Maddie in Liv's life. He was dedicated to her, but for her Maddie always came first. It was a tricky situation that they ultimately couldn't resolve. Mind you, also worth a mention is Maddie’s devastating breakup with Diggie. Right after returning from a semester away, he signed up for another without even mentioning it to her. And when she tried to have an honest talk with him about it, he acted like her feelings didn’t matter.

#4: Alex Russo & Mason Greybeck

“Wizards of Waverly Place” (2007-12)

When Alex is up for the Wizard of the Year award, her boyfriend should be supportive, right? Well, Mason was too busy brooding about a fake story that Alex was dating another guy. He dealt with his feelings by attacking the other guy and completely ruining Alex’s award ceremony. Alex broke up with him on the spot! We’re sad for Alex, but arguably, that was a good call. In Transylvania, Mason attacked Justin and Juliet, costing her her vampire powers - and leading to more broken hearts. Not saying that this is all Mason’s fault, but he is the common denominator in both incidents.

#3: Teddy & Spencer

“Good Luck Charlie” (2010-14)

When Teddy found out Spencer was cheating and she teamed up with the other girl to humiliate him, we were all saying good riddance along with them. But when they got back together, Spencer was a totally different guy and we were all learning to trust him again. Which only made it hurt more when Spencer got accepted to a performing arts school and it was an opportunity he just couldn’t pass up. They decided that long distance wouldn’t work and broke up in order to remain friends. Though it was a very mature decision, it still hurt the both of them, making the scene difficult to watch. Hurting too much to say goodbye to each other, instead they said hello.

#2: Ally Dawson & Austin Moon's Second Breakup

“Austin & Ally” (2011-16)

Being relationship partners and music partners proved to be too much for this couple. As their careers reached an all time high, their relationship hit an all time low. Austin's "people" didn’t think he should have a girlfriend for his image, and Ally didn’t want to be kept a secret. She decided they should end things and remain friends rather than they both be unhappy. Since their careers were taking them in different directions anyway, they recognized that the timing just wasn’t right for them. Though it may have been the right decision for the time, you can’t help but get teary eyed at hearing Austin say he doesn’t want to lose her again.

#1: Raven & Devon

“That’s So Raven” (2003-07)

Raven and Devon took a while to get somewhere really good, but Devon truly understood Raven, and not only accepted all her crazy, but loved her because of it. So it was not only heartbreaking, but genuinely infuriating when he moved away. Raven had to find out on her own that Devon's dad was getting remarried and moving the whole family away. Devon acted shady during his last few days, driving Raven crazy, and didn’t tell her the truth until she confronted him at the wedding dressed as the bride. They had a few nice moments before he left, but Raven was completely destroyed.

Are there any soul-shattering Disney breakups we missed? Share the sadness down in the comments!