Many years ago Merlin is looking for the Dark One. The Dark One destoryed the only woman he ever loved. He goes after the Dark One who uses his heartbreaking tear to turn him into a tree.
Emma sees this all through a dreamcatcher, which also has shown her the spell Arthur put on his parents, thanks to her dark magic. Regina is still wary of the Charmings now that they are supporting Arthur. She keeps asking them if they are sure they should trust him while leading them to the dagger. Emma shows up just in time to prevent Regina from giving the dagger to her parents. She tells Regina that Arthur plans to kill Merlin. Emma wants to keep taking the risk of using dark magic to free Merlin, but Regina is worried.
Regina learns that Merlin was trapped due to his sadness over lost love, and she thinks they might be able to save him the same way.
Henry and Violet are bonding over her horse and dead parents. When Violet leaves Henry alone, he attempts to be a hero by playing with a sword, but is discovered by Violet’s father, Sir Morgan. He sees that Henry has no skills with a sword. Henry says he is a writer which Sir Morgan is not impressed with.
Regina and Emma come across Henry and find him practicing with a sword. He wants Violet to think of him as worthy. They try to tell him to just be himself. Henry takes the advice and leaves a note for Violet to meet him at Grannys. Violet is happy until she realizes what Henry wants. She says she doesn’t feel the same way about him that he feels for her.
Regina watches the dreamcatcher and watches the moment her mother ripped Daniel’s heart out. Emma gets her tear, but it’s been too long since Daniel and now that she has Robin she is pretty much healed. They are interrupted by Henry, who says he acted like himself and got rejected. Emma uses Henry’s tear and uses enough dark magic to free Merlin.
They find out that the sword can erase dark magic forever, but it can also destory light magic too. Merlin says he can free Emma from the darkness if her heart is ready to be free.
Everyone is trying to figure out how the squire disappeared. Henry suggests they have a dance to help everyone relax. Snow is excited and gets ready to prepare when Belle shows up to tell them that Rumple is missing.
Rumple is with Emma, who asks him to pull the sword. Rumple says he can’t and tries to talk Dark One reasoning with Emma, but she doesn’t want to listen. She calls Merida in and uses her heart to control her to take Rumple into the forest to make him a hero.
Merida is not getting through to Rumple and he continues to be unwilling to fight. She just wants to go home, save her family and the sooner she makes him brave, the sooner she can get her heart back and get on with her life. She eventually steals the chipped cup and uses it to give him something to fight for. It works and gets Rumple to take a few swings, but he has a long way to go.
Regina, Hook, Belle and Robin try to break into Emma’s house to see what she is hiding, but it’s protected by a spell so no one can enter. Regina conjures a scarf of Henry’s and opens the door. They find the sword and see that the dagger and the sword are one and Belle concludes that Rumple was being held here. Regina gets a text from Henry that Emma’s on her way back, and they leave, but not before Hook notices the dreamcatcher Emma had been staring at earlier.
Violet is feeling down because her horse is missing. Henry says he will get Emma to help him find it. Emma agrees to help Henry. Violet’s horse likes pumpkins so Emma takes them to Peter Peter’s Pumpkin Patch. They get there and find the horse. He gets a kiss, a hero entrance and her dad’s approval.
Robin and Regina use the dreamcatcher from Emma’s to see what happened to her in Camelot. She visited Violet in the stables after she found the note about meeting Henry for dinner. Emma takes her heart out and forces her to break things off with Henry because she needs fresh heartbroken tears. It also turns out that Henry overheard everything and his view of Emma is shattered.