Over its seven-year run, Once Upon a Time gave audiences some of the best love stories about romance and family; however, the show didn't shy away from hard-hitting, upsetting storylines either. Once Upon a Time wasn't afraid to kill off some of the show's main characters, leading to heartbreaking moments of loss and grief for those within the show. Once Upon a Time entwined a fictional story of magic and fairy tales with characters experiencing the same feelings as real people, the good and the bad.

One thing the show excelled at was creating emotional moments by making the audience feel for the characters. Whether they had just lost a member of the notoriously convoluted Once Upon a Time family tree, had their declaration of love rejected, or found themselves afflicted by some kind of curse, the showrunners upheld these heart-wrenching moments across all seven seasons. Among the many heartbreaking, upsetting moments from Once Upon a Time, a few still stand out as the saddest.

10 Emma Sacrifices Hook To Save Her Family

Season 5, Episode 11: "Swan Song"

In "Swan Song," Hook meets his demise after three and a half years on the show. It isn't like other sacrifices on the show: Hook has to be stabbed through the chest with Excalibur by Emma Swan, his true love. If he wasn't killed, the power of the Dark One would have killed every living thing in Storybrooke. Emma's reluctance, the darkness surrounding them, the upsetting background music, and the emotion from all the actors present all contribute to the scene's impact.

Hook's death came after Emma was scared to open herself up to the possibility of love when all her ex-boyfriends died. Hook made a promise to Emma that he wasn't going anywhere and that the one thing in life he was good at was surviving. The fact that Emma has to be the one to end Hook's life, especially after this conversation, makes the scene even more heartbreaking. However, the scene luckily paved the way for a new storyline where the heroes bring Hook back from the Underworld.

9 Cora Tells Regina That She Would Have Been Enough

Season 2, Episode 16: "The Miller's Daughter"

Cora Mills is the main villain for the majority of Once Upon a Time's second season. She is the most dangerous villain the heroes have faced off against at this point, as she doesn't have her heart inside her chest, meaning she can’t feel love or empathy, she only wants power. However, the arc shockingly concludes when it appears that Snow White is trying to help Regina and Cora with their mother-daughter relationship by giving Regina Cora's heart to put back in her chest.

However, when Regina returns Cora's heart, Cora dies almost instantly, with Regina realizing that Snow had cursed the heart. Before she dies, Cora tells Regina that she would have been enough. This scene is truly upsetting as Cora always favored power over her daughter, and usually only used Regina to gain more power. She'd shown Regina little love or affection. So, when she tells Regina that she would have been enough for her before she died, it shows that Regina might have had a family that loved her, it was just too late.

8 Maleficent Loses Her Daughter

Season 4, Episode 17: "Best Laid Plans"

Maleficent's limited screen time doesn’t make her saddest scene any less heart-wrenching. In season 4, it is revealed that Maleficent's heartache comes from losing her child, who was taken from her. Snow White and Prince Charming kidnap Maleficent's unborn child, Lily, while she is in an egg to place a spell on her to transfer Emma’s potential for darkness into Lily. The two "heroes" didn't realize that the spell would also send Lily to the real world.

The circumstances of this scene are saddening, but the thing that makes it truly heartbreaking is the performance of Kristin Bauer Van Straten as Maleficent. The way she pleads with the Charmings to return her child and the scream she lets out as they take the egg is utterly tragic. Lily being kidnapped and taken away from her mother by two people often perceived as heroes is difficult to watch, while also providing Maleficent's character with more layers, gaining sympathy from the audience.

7 Robin Hood Sacrifices Himself To Save Regina

Season 5, Episode 21: "Last Rites"

Robin Hood is introduced in the show's second season, where Robin was played by Tom Ellis but was later recast, the role was taken over by Sean Maguire. Most of his storylines revolve around his growing relationship with Regina, which makes his eventual death scene especially unfair. Robin meets his untimely end in season 5 when he jumps in front of Regina as Hades blasts magic at her to try and kill her; Robin intentionally sacrifices himself to save Regina's life.

Regina also took a while to open herself up to love after her first fiancé was killed by Cora. Yet Regina finally gave Robin a chance, and they lived happily for a while until Robin's death. When Robin dies, Regina loses her true love. His spirit lingers for a few seconds after his ing, giving Regina a look that said goodbye. The scene ends with Regina and Zelena on the floor in tears, comforting each other. It is devastating to see Regina lose someone else she loved in such a terrible way.

6 Regina Blames Zelena For Robin Hood's Death

Season 6, Episode 1: "The Savior"

After Robin's death towards the end of season 5, the show's sixth season looked promising for Regina and Zelena's sisterly relationship when Regina invited Zelena to move in with her. The two sisters are getting along great for the first five minutes, but towards the end of the season 6 premiere, Zelena realizes that Regina blames her for Robin’s death, so she moves out.

This scene may not seem as upsetting as the others at first glance, but when Zelena's family history is considered, this scene is still sad. Zelena was given up as a baby, her adoptive father hated her, and she was never good enough for anyone. When Zelena finally thinks she has a sister who loves her, she finds out that Regina resents her for her boyfriend's death. This is a betrayal of Zelena's trust which took so much for Regina to earn, and it is frustrating to see the hard work of these two sisters thrown away.

5 Neal Sacrifices Himself To Save Storybrooke

Season 3, Episode 15: "Quiet Minds"

Neal finally re-enters Emma and Henry's lives in the wildly shocking season 2 episode "Manhattan." Unfortunately, the character only lasted a season before being killed off. Throughout his run on the show, Neal always protects Henry and Emma despite only being in their lives for a short time. At the end of the second season, he is presumed to be dead, but he has just been sent back to the Enchanted Forest. In season 3, he disappears for three episodes, with no one knowing where he is, prompting fears again of him being dead.

Neal had cast a spell to bring Rumpelstiltskin back to life in exchange for his own life.

Luckily for Emma, Neal turns up — just to be killed off in the same episode. Neal had cast a spell to bring Rumpelstiltskin back to life in exchange for his own life. Therefore, Neal sacrificed himself so Rumpelstiltskin could tell the heroes the identity of the Wicked Witch. Neal unfortunately dies in Emma's arms, reminiscing about their past and how they never made it to Tallahassee together. The scene is one of the first major death scenes of the show and changes the tone of the story being told.

4 Snow White Tells Prince Charming That She Doesn't Love Him

Season 1, Episode 10: "7:15 A.M."

Back in the very first season of Once Upon a Time, Snow White and Prince Charming don't have the easiest start to their relationship with all kinds of obstacles in their way. One of them ends up creating one of the saddest scenes of the show's first season. In the flashback of episode 10, Snow White breaks into the castle to tell Charming about her feelings for him. Before she can find him, she is kidnapped by King George, who threatens to kill Charming unless she breaks his heart and tells him that she doesn’t love him.

Desperate to protect her true love, Snow White goes to his room and says this, and that he needs to get over her. Although the audience already knows that Snow and Charming get married and have baby Emma before the curse hits, it doesn't make this scene any easier to watch. Both Snow and Charming are left heartbroken, with Charming begging for a chance and Snow shutting him down. The scene that follows with Snow walking through the woods somberly with the Dwarves just emphasizes the effect.

3 Graham Dies As He Re His Past

Season 1, Episode 7: "The Heart Is A Lonely Hunter"

When all the fairy tale characters are cursed in the show's flagship season, Sheriff Graham is one of the first to regain his memories and who he is. This comes just moments after he kisses Emma, and just before he is murdered by Regina. Regina was losing her control over Graham, so she decided to just get rid of him rather than potentially threaten her and the curse's hold on the town.

It takes a lot for Emma to trust someone after everyone in her life has abandoned her. However, she finally kisses Graham, itting her feelings to be stronger than something casual. However, as they kiss, Regina crushes his heart to dust, and he dies right in front of Emma. The scene is horrific and heartrending, especially because of Jennifer Morrison's performance as Emma when she is standing over Graham's body, crying, desperate to revive him, as she realizes there is nothing she can do.

2 Rumpelstiltskin Loses Baelfire Through The Portal

Season 1, Episode 19: "The Return"

One of the saddest storylines of Once Upon a Time is of Rumpelstiltskin choosing his power over his son and ending up losing him for centuries. In a season 1 flashback, Rumpelstiltskin has the chance to give up his magic as the Dark One by traveling with Baelfire to a land without magic. Initially, he agrees, but just as they rea about to jump through the portal, Rumpelstiltskin's survival instincts take over, and his son falls through the portal while he stays in the Enchanted Forest.

This scene is truly heartbreaking to watch because of Baelfire's evident emotions of being betrayed and abandoned by his own father, but also because of Rumpelstiltskin's reaction when the portal closed. He knew he wanted to go with his son, but his change of heart came too late. Robert Carlyle's performance is incredible during this scene, and it comes through how much Rumple cares for his son, in conflict with his insatiable desire for control.

1 Belle Commands Rumpelstiltskin To Leave Storybrooke

Season 4, Episode 12: "Heroes And Villains"

One of the most standout scenes in Once Upon a Time comes from season 4. In the mid-season finale episode, Belle finds out Rumpelstiltskin is still up to his wicked ways, so she uses his dagger to command him to leave Storybrooke forever. The scene is upsetting and surprising because Once Upon a Time rarely sees people ending a relationship for internal reasons, only made more effective by the performances of Carlyle and Emilie de Ravin and Robert Carlyle.

It is one of the first times Belle properly stands up to Rumpelstiltskin in Once Upon a Time.

It is one of the first times Belle properly stands up to Rumpelstiltskin in Once Upon a Time. She had made her opinions known before, but this was the first time they went face to face. Even though she had always believed the best in him before now, she finally realizes that he will never change, and she uses all her strength to force him out of town and out of her life. The scene is very empowering, but also devastating, as it feels like the end of an era for the two characters.