When a story is focused on love, it will inevitably feature heartbreak as well. This was definitely true of the television series Once Upon A Time where the show's relationships created moments that could be wholesome, passionate, or sometimes downright heartbreaking.
Fans became invested in the various romantic and platonic relationships shared between characters like Snow White, Prince Charming, Emma Swan, Regina Mills, Rumplestiltskin, Belle, and many others. Most of the show's particularly poignant moments can be traced back to these core relationships, especially when the relationships reached a tragic juncture, an unthinkable sacrifice, or a harsh truth.
10 Snow Crushes Charming's Heart
The person who casts the Dark Curse has to crush the heart of the person they love most. In season 3, this meant that a pregnant Snow White had to crush Prince Charming's heart in order to cast the Dark Curse so they could get back to Emma and defeat Zelena.
After the purity of their love and everything they endured, it was heartbreaking to see Snow crush the heart of her beloved Charming. Fortunately, this was not the end of Charming as Snow split her own heart in two. Her love with Charming was so strong that they could literally share one heart and both survive.
9 "You Would've Been Enough."
Regina spent her whole life feeling as though she was never good enough for her mother Cora. She felt like a disappointment and there was inevitably a great deal of tension and resentment in their relationship.
As Regina cradled Cora in her final moments, though, Cora said, "This . . . would've been enough. You . . . you would've been enough." While this was the most meaningful thing Cora could have said before she died, it was also gut-wrenching for them both to realize that things could have been different and so much better between them.
8 Belle Banishes Rumplestiltskin From Storybrooke
Belle eventually realized that Rumplestiltskin was lying to her in season 4. With the Dark One dagger in her possession, Belle commanded Rumplestiltskin to take them to Storybrooke's town line. She confronted him about his abusive lies, how his true love was his power rather than her, and that he'd never prioritized her over his own power.
Despite his desperate excuses and pleas that he would change, Belle refused to turn a blind eye any longer and used the Dark One dagger to force him over the town line. She essentially banished him from Storybrooke as he wouldn't be able to return once he crossed the town line without any kind of magic to come back. This couple had shown they could work together in the past, so while this was an important step for Belle to take, it was also devastating to see that their relationship had come to this.
7 Rumplestiltskin's Self-Loathing Rage
"Skin Deep" will always be one of Once Upon A Time's best episodes. It did a particularly good job of blending the flashback and present timelines together when Rumplestiltskin unleashed his self-loathing rage. In the flashbacks, he hated himself because he couldn't believe that Belle actually loved him, convinced that her kissing him couldn't be genuine and must somehow be a manipulative move to weaken him. His explosive response to this led to even more self-loathing as he felt responsible for driving away the only person who loved him.
This was juxtaposed with Rumplestiltskin beating Belle's father in the present timeline, blaming her for driving her away. The juxtaposition made it clear that Rumplestiltskin really blamed and hated himself for what he believed happened to Belle. This depth of self-loathing and inner torment was heartbreaking and part of what made Rumplestiltskin such a nuanced and tragic character.
6 Graham's Death
Graham was Once Upon A Time's first heartbreaking death. Moments after he kissed Emma and finally remembered his life as the Huntsman, Regina crushed his heart and killed him.
Fans were so happy to see Graham breaking free of Regina's influence and making his own choices as he fell in love with Emma. Losing him was a tough loss, though it did an effective job of elevating the stakes and proving that no one was truly safe in this fairy tale adaptation.
5 Emma Has To Kill Hook
In order to destroy the Darkness, Hook trapped the Darkness within Excalibur and implored Emma to kill him. Hook regretted giving in to the Darkness during his time as the Dark One and felt the only way to atone for his mistakes and to save everyone was to die a hero by destroying the Darkness once and for all.
Emma and Hook's relationship had come a long way and the audience sobbed right along with Emma as she plunged Excalibur through the love of her life. This will always be an intense, emotional moment and was only softened by the fact that Hook was eventually resurrected and he and Emma were able to reunite in the land of the living.
4 Belle's Death
Belle's death wasn't as tragic as the other big deaths in the series, but it was still crushing. Belle grew old after building a beautiful life together with Rumplestiltskin. She knew she would grow old and pass away before he did, but she committed herself to this fate so she and Rumplestiltskin could finally spend many blissful years together.
Even though she took control of her fate and passed on peacefully with the promise that she and Rumplestiltskin would ultimately be together in the afterlife, it was still difficult to lose a beloved character like Belle.
3 Robin Hood's Sacrifice
Robin Hood gradually became one of the show's more important characters. He and Regina developed a wonderful relationship. He appreciated her, adored her, and helped her see how truly special she was as a person. Regina suffered a great deal throughout her life and she deserved all the happiness she experienced with Robin.
Considering what Robin meant to Regina and him being a likable character in general, it was devastating to see him sacrifice his life. When Hades tried to kill Regina with the Olympian Crystal, Robin leaped in front of her and was stabbed instead. The Olympian Crystal not only ended his life, but it obliterated his soul, which meant he wouldn't go the Underworld and be able to move on.
2 Neal's Death
Some fans might disagree, but losing Neal/Baelfire was arguably the most tragic death in the show. Neal was Henry's father, Rumplestiltskin's son, and Emma's first love. Henry spent most of his life without a father and Rumplestiltskin spent centuries trying to reunite and reconcile with his son.
This important person was back in the lives of Henry, Rumplestiltskin, and Emma and his return influenced them in positive ways. His death took him out of their lives again, only this time it was permanent, and once again Henry was left without a father and Rumplestiltskin without his son.
1 Rumplestiltskin Learns That He Can't Save His Son
When Emma and Hook ended up accidentally time-traveling to the past, they encountered Rumplestiltskin. Before Emma returned to the present, Rumplestiltskin confronted her about whether he finds his son in the future and if his son forgives him. A tearful Emma explained that he does find his son and Neal forgives him, but that Neal dies.
A heartbroken Rumplestiltskin thinks that he could change the future and save Neal, but Emma makes him promise that he won't as changing the timeline could make things worse and rob Neal of his heroic death. Rumplestiltskin has to drink a potion to make him forget what he learned and it's the moment before this that is truly heartbreaking as Rumplestiltskin learns that his son will die and that he has to accept that there's nothing he can do to save his child.
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