Top 10 Saddest Cartoon Breakups

Poor, sweet Bolin. The Earth Bender had been smitten with Korra practically from first sight, and as they became friends he remained blissfully unaware of her crush on his brother. But with Mako dating Asami, Korra agrees to go out with Bolin. The two seem to really click over their similar sense of humor and their shared taste in food. It’s no good though. Mako and Korra can’t deny their feelings for each other, and Bolin is the one who gets hurt. Their romance might have been brief, but seeing such a lovable guy so devastated is hard to take. We know things worked out fine for him in the end, but we still hate to see him crushed.

Arguing is a part of every normal, healthy relationship, but this fight was neither of those things. When Wanda attempts to talk about BoJack’s bad mood, he quickly makes things almost viciously personal. For an animated show, this moment feels uncomfortably realistic. As Wanda defends herself and her work it quickly becomes clear that a rift has opened between the couple that won’t be overcome. Wanda is right when she points out that BoJack’s bad experiences are no excuse to treat her poorly. BoJack just isn’t willing to change though. As brutal as it was to sit through this breakup, we have to appreciate the wisdom in Wanda’s parting observation.

While we always knew Star and Marco were destined for each other, there was still something really sweet about seeing Marco get a chance to date Jackie, the girl he’d been crushing on since kindergarten. They seemed to have a really solid relationship too. Except for one big roadblock. While Marco claims to be happy on Earth, Jackie realizes that his heart is still in Mewni. For some couples this would spell drama. Jackie takes it all with a refreshingly mature perspective. Marco is still in denial about his deepest feelings though. As gentle as this breakup is, losing your first love is always tough. Even if Jackie is right, Marco is clearly hurt all the same, and we can’t help but sympathize.

After watching the gradual build up of Mordecai and Margaret’s feelings for each other, we were ready to finally see these two love birds just be together already. By the time Mordecai is ready to define the relationship, it seemed like even an FBI raid couldn’t knock them off course. In fact, the dramatic backdrop almost makes the big question more endearing. As TV audiences we expect a romantic moment here. So we definitely weren’t ready for the bombshell that Margaret dropped. Though she says that she can see a future for their relationship, she prioritizes her dreams over her feelings for Mordecai. We understand her decision, but that doesn’t mean we aren’t disappointed to see them split up.

This curveball hit us all hard. Rocked by Rose’s betrayal, Garnet unfuses in a moment of crisis. The normally level-headed Sapphire is deeply shaken by the unexpected turn of events, especially the implications it has for her relationship with Ruby. In her inability to make sense of any of it she blames both herself and her other half for not seeing the truth sooner. Nothing anyone says seems to calm her down. In that moment Sapphire can’t even trust in the most fundamental things she believed. Ruby’s devastation is awful, but even worse is when Sapphire realizes her mistake only after it might be too late for Garnet. To see this stable, loving relationship almost fracture forever nearly broke us.

Sometimes the sad truth is that no matter how much you care about someone, life will still get in the way. Ginger and Darren had been life-long friends before they fell for each other, but as they grew up it was clear they were moving in separate directions. Ginger is committed to making their relationship work no matter what. Darren, on the other hand, can’t see a future where they’re happy together. We don’t know what’s worse, the unexpected nature of the breakup, the fact that it ruined their friendship too, or that Darren did it to be with someone else. Not even because he liked her more, just because it was easier. We wanted so much better for Ginger.

People don’t always represent themselves authentically early in their relationships, but this was on another level. For Green Lantern it was bad enough learning that Hawkgirl was on Earth as a Thanagarian advance scout. It was worse finding out she was actually engaged to their leader Hro Talak. You’d think that would be more than enough emotional baggage for one breakup. Even Green Lantern’s Justice League teammates know he’s been through the wringer. When the Thanagarians’ true motives are revealed, though, it turns out that things could still get messier. Face to face on the field of battle, Hawkgirl makes one last emotional appeal to Green Lantern. Few romantic splits manage to be physically, mentally, and emotionally as painful as this one.

Appropriately, given the title of the show, this couple had no shortage of drama throughout their relationship. It was always obvious that Gwen and Trent were perfect for each other though. Unfortunately, things start to unravel between them when they find themselves on opposite teams. Trent’s jealousy over Gwen’s friendship with Duncan certainly didn’t help matters. When she found out he was throwing challenges for her, Gwen decided it was best to call things off. We might have been able to accept it if that was the end of the story, but then Gwen conspired to get Trent kicked off the show entirely. It just seemed unnecessarily mean all things considered.

When a conflict between Flame Princess and the Ice King gives Finn a strange, but pleasant dream, he becomes obsessed with recreating it at all costs. And when he finds out that his dream might be prophetic, he writes misleading letters to both parties in order to push them into a full scale battle. It doesn’t take long for Finn to realize that he’s made a mistake, but by then the damage has quite literally been done. In desperation, he comes clean to Flame Princess. Though he tries to explain himself, Flame Princess is deeply hurt that he would manipulate her. As she leaves him behind, the Frost King ably sums up the whole debacle.

Before we unveil our top pick, here are a few honorable mentions.

Serena & Wyatt, “6teen” (2004-10)
A Text Message Is Never the Right Choice

Luann & Kirk Van Houten, “The Simpsons” (1989-)
Public Breakups Are Always the Worst

CJ & Mordecai, “Regular Show” (2010-17)
There’s a Time and Place For This Kind of Thing, and Neither Is At Someone Else’s Wedding

Terra & Beast Boy, “Teen Titans” (2003-06)
An Especially Rocky Ending to a Budding Romance

Sokka and Yue were attracted to each other from the very beginning, but their relationship kept hitting snags. First there was Yue’s engagement to another man, and then, well, everything changed when the Fire Nation attacked. After the villainous Admiral Zhou destroys the Moon Spirit, Yue is called to make the ultimate sacrifice to save her people and the world. Knowing that she’s doing the selfless, heroic thing doesn’t make losing her any easier for Sokka or for the audience. In fact, it just makes their separation seem that much crueler since they are literally torn apart my destiny. It was tragic for both of them, but we especially feel for Sokka here. After all, who could possibly relate to a breakup like his?