Top 10 Saddest Once Upon a Time Moments

Snow and Charming’s plans go awry when Snow unexpectedly goes into labor, leaving the new parents with a devastating decision to make. No parent should be forced to give up their child, but with the curse looming, they realize they’re out of options. They send baby Emma through the wardrobe alone to give her her best chance and hope that one day she’ll find them. Snow’s cries are heartbreaking but as Charming is wounded at the final hurdle, he stays conscious long enough to make sure his daughter is safe.

Until now Rumplestiltskin has enjoyed immortality, but watching Belle grow older gives him a change of heart. While he would go to the ends of the earth to find the solution, Belle would rather enjoy the time they have together. What follows is a beautiful montage of the couple building their new lives and living it to the fullest until Belle’s dying day. Rumple is devastated, but Belle reminds him that they always manage to find their way back to one another. And when they do reunite, we were weeping all over again.

To counter Pan’s curse, which will wipe out Storybrooke and all its residents, Regina finds a way to rescue everyone - but it comes at a cost. This is the second time Regina is forced to give up the person she loves most, but at least this time it’s for the greater good. We hate having to watch Emma and Henry say goodbye to their loved ones as another curse splits the family. Regina’s only consolation is to give Henry and Emma new memories to replace the ones they’re about to lose.

Snow and Charming are pretty much couple goals, but they’re heroes first, even if that means giving up the thing they love most. The dark curse is the only option to save everyone from Zelena, but this time Snow has to cast it using Charming’s heart. As Snow holds the heart, he tells her not to say goodbye while she tells him she loves him more than anything. Even Regina’s heart thaws at their parting words, but we can live with the solace that Snow and Charming will always find each other.

The Sheriff of Storybrooke keeps having flashbacks of his former life and on top of that, he’s conflicted between his relationship with Regina and feelings for Emma. Regina literally has his heart, and she is furious that Emma has turned his head, even going as far as saying she’s stolen him. It takes Emma forever to accept her feelings for Graham, but it’s too late. Her kiss wakes him from the curse and he remembers who he is. However, just as he does, Regina crushes his heart and he dies in Emma’s arms.

Rumplestiltskin’s relationship with power is stronger than his love for anything or anyone else. Belle hopes she might finally be the exception - until she learns that he’s been deceitful. She uses the dagger to stop Rumple and whisks him to the town line where she banishes him from Storybrooke. We’re gutted for the heartbroken Belle and we can’t help but feel a bit sorry for Rumple too as he stumbles across the town line. The real stinger comes when Belle says that she no longer sees the man behind the beast.

Another victim of Rumplestiltskin’s thirst for power is his son Baelfire. When your dad is the Dark One, life isn’t so rosy, so Bae tries to convince his father to join him in a land without magic. However, when the time comes, Rumple can’t follow through. Despite being abandoned, Bae grows up with a good heart, and always willing to make the ultimate sacrifice for those he loves. The clincher here is that as everyone says their final goodbyes, Henry remains unaware that the man they’re burying his father.

Regina is unlucky in love and it seems that she and Robin just weren’t meant to be. First, they’re separated to save Marian’s life, and then their second shot at happily ever after is destroyed by Hades. We’d just finished wiping away the tears as Emma leaves Hook in the Underworld before we’re faced with this other devastating moment. When Hades tries to kill Regina, Robin steps in and takes the bullet. She’s completely helpless as she watches the man she loves disappear before her eyes and we’re distraught for her.

Hook has happily given in to The Darkness until it almost kills the woman he loves. Realizing this isn’t the man he wants to be, Hook absorbs all The Darkness and begs Emma to kill him in order to destroy it. Of course, she’s inconsolable over the idea but she also knows that it’s the only way to save everyone. Just try not to well up as Emma is forced to kill the man she loves. Her only consolation is knowing that he died as he always wanted: as a hero.

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

Emma Breaks Her Engagement
“Page 23”

Maleficent Begs The Charmings Not to Take Her Egg
“Best Laid Plans”

Emma Walks Away from Lily
“Breaking Glass”

Liam Gets Poisoned by Dreamshade
“Good Form”

Ingrid Sacrifices Herself
“Shattered Sight”

This is the tragic love story that started it all. Regina plans to run away with her stable boy lover, Daniel, until a well-meaning Snow White reveals her secret. Cora has other plans for her daughter’s future and puts an end to this love story by crushing Daniel’s heart. We’re heartbroken for Regina as she doesn’t even get a chance to say goodbye before her lover is killed before her very eyes. Even their brief reunion gets us reaching for the tissues, as Regina is forced to let him go once again.