As a child, Rumplestiltskin watches his father, Malcolm, swindle a participant out of money in a rigged card game and then get beat up for it, though he tries to intervene to protect his only parent. The man steals Malcolm's money, leaving both father and son penniless. Rumplestiltskin is sent to a pair of wool spinners while his father goes off to look for work. Reluctant to be left behind, he is consoled when presented with a straw doll by his father. Urged by his father to name the doll so it can be his protector, Rumplestiltskin chooses "Peter Pan". For the duration of his stay, he becomes quite good at spinning wool; earning praise from the spinsters. They suggest he can spin for kings and queens one day. Pleased, Rumplestiltskin envisions earning money so he and his father can be together. The spinsters state Malcolm's reputation as a cheat and coward will never die down. They hand Rumplestiltskin a magic to take himself to another land, and reveal his father is continuing to swindle people out of money. In disbelief, Rumplestiltskin goes to find his father at the pub. Despite his father's terrible ways, Rumplestiltskin suggesting they start afresh together by using a magic bean. Malcolm recalls the phrase "think lovely thoughts", which he often said to himself at night during his difficult childhood years, and traveled to a wonderful place called Neverland in his dreams.
They use the bean to reach Neverland, where Malcolm quickly realizes he can no longer fly as he did in his boyhood years, and proposes they look for pixie dust so the feat is possible again. Rumplestiltskin waits beneath the tree as his father climbs up. A moment later, Malcolm gives up on his dream of flying because adults don't belong in Neverland, so Rumplestiltskin advises they can try another land as all that matters is being together. Rather than that, Rumplestiltskin is grabbed by the Shadow, but manages to hold onto his father, who reveals he wants to stay in Neverland alone and regain youth. Rumplestiltskin is let go by Malcolm and whisked up higher as he drops his doll and watches his father transform into a young boy. Dropped back home, Rumplestiltskin seeks comfort at the spinsters' cottage as he cries over his father's abandonment. The spinsters offer him a home with them. On a lesser level, Rumplestiltskin is upset his doll, Peter Pan, is gone forever. ("Think Lovely Thoughts")
When Rumplestiltskin is older, he marries a woman named Milah, and together they live in a village spinning and selling wool. One day, he is drafted to fight in the ogre war; excited to prove himself and show that he is not a coward like his father. However, in the training camp, the prisoner he is assigned to watch over as his first task—a Seer—indicates she knows of his fate, and would gladly exchange this information for a glass of water. She tells him that Milah is pregnant, and that his actions on the battlefield will leave his son fatherless. Skeptical at first, Rumplestiltskin eventually believes what she says and intentionally injures himself, so that he can get out of the war and be with his son, Baelfire. Once he returns home, Rumplestiltskin attempts to explain to Milah about the seer's prophecy, but she is astonished that he is gullible enough to believe in such a thing. Disgusted with his cowardice, she argues it would have been much more honorable for him to die and for Baelfire to have a dead father that fought in the war. ("Manhattan")
As the years pass, Milah grows more and more disillusioned and unhappy with the life she has with Rumplestiltskin. She drinks and gambles at the bar with a pirate captain, Killian Jones, and his ship crew men. He comes by to bring Milah home, to which she jeers and mocks him for his cowardly reputation. From outside, Baelfire comes in asking for his mother, and only then does Milah depart for her son's sake. At home, Milah tries to persuade Rumplestiltskin that it's possible for them to have a better life in another place where he doesn't have to live in the shadow of his reputation and they can travel the world. Instead, Rumplestiltskin pushes her to make the marriage work for Baelfire. She reluctantly agrees, but the next morning, he hears word of Milah's kidnapping by Killian. Rumplestiltskin attempts to rescue his wife, but is turned away by Killian when he is too cowardly to duel with him. Regretfully, he returns home to tell Baelfire that his mother is dead. ("The Crocodile")
When the kingdom resorts to using children as soldiers in yet another ogre war, Rumplestiltskin and his son flee into the forest, only to be found and bullied by royal knights. After the knights leave, Rumplestiltskin and Baelfire are approached by a mysterious old man who offers them help in exchange for a small amount of food and company. After Rumplestiltskin explains his reason for running away, the old man has a better idea and steers him towards stealing a magical dagger from the Duke's castle. As holder of the dagger, Rumplestiltskin can control the Dark One, a terrifying entity with unmatched magical powers who is the most feared being in all the land. He decides to steal the dagger with the hopes of protecting Baelfire and turning the Dark One into a force of good. However, Rumplestiltskin can't see himself keeping the Dark One as a slave as he is terrified of him. Convinced he has no other choice, Rumplestiltskin sets fire to the Duke's castle and makes off with the blade. Afterwards, he meets Baelfire in the forest and sends him home. Once alone, Rumplestiltskin summons the Dark One and cowers at the being's presence. When the Dark One taunts him about Baelfire not truly being his son, Rumplestiltskin stabs the entity in a fit of blind rage. Shockingly, he discovers the Dark One is the old man who told him about the dagger. The man briefs on all the horrible deeds he was forced to do as the Dark One and states death is welcome release and ominously warns Rumplestiltskin that "magic always comes with a price". Then, Rumplestiltskin's own name replaces Zoso's on the dagger, and he gains the powers of the Dark One. Relishing over his new-found status, he returns home to humiliate and kill the knights who harassed him and his son while Baelfire looks on in terror. ("Desperate Souls")
As Rumplestiltskin continues his reign as the Dark One, he keeps Baelfire constantly at home and doesn't allow him to be outside. One day, he returns home with a knife as a present for his son. Upset, Baelfire knocks it off the table and proclaims he wants nothing his father gains from being the Dark One. Rumplestiltskin learns what Baelfire desires most is freedom, but he misunderstands and thinks his son wants to live in castle. As he hastily suggests procuring one right away, Baelfire says he wants to go out and have friends. Rumplestiltskin forbids it as this will be an easier way for his enemies to kidnap his son and hold him captive. However, Baelfire wonders if his father's protectiveness is actually a fear his own son will leave and never come back. His son's words strike a nerve, but Rumplestiltskin quickly asserts his feelings are simply out of concern for Baelfire's safety as he doesn't want to ever lose him. He returns home the next day with a crown for Baelfire to wear to go along with the castle, but his son is gone. After tracking Baelfire to the small town of Hamlin, he discovers from the townspeople that all the children in the village disappeared the prior night when there was a sound of a flute playing, and it's possible Baelfire went as well.
During the night, Rumplestiltskin watches as boys sneak out of their homes and are guided by the sound of a pan flute to a campfire where many youngsters dance around fervently in animal masks. He is not able to discern which one is Baelfire, but spies the cloaked piper and runs over to snap his flute in half. As the stranger takes off his hood, Rumplestiltskin is shocked to see the piper is Peter Pan, who he remembers as the person his father became. Steeling himself against Pan, Rumplestiltskin questions him about his reason for taking Baelfire. Pan admits it's lonely in Neverland and wants a few companions, especially since only certain boys filled with loneliness can hear the instrument's music, further explaining why Rumplestiltskin heard it as well. Rumplestiltskin is pushed around by Pan, who accuses him of craving power, but in actuality, is nothing more than an unloved, lonely lost boy. When Pan alleges Baelfire is already part of his group, he also challenges Rumplestiltskin's various abandonment issues. To put Rumplestiltskin's trust in his son to the test, Pan commands him to ask his son if he wishes to stay or leave out of free will. Rumplestiltskin ignores him and whisks Baelfire home with magic. Back at home, he attempts to help an angry Baelfire see the dangers by disclosing his own past relationship with Pan, stating he knew him as a boy, but was betrayed in the end. Even so, Baelfire shares his knowledge of the deal Pan offered his father. He also states Pan said his father's trust and love for him would be proven by allowing a choice of free will. To Rumplestiltskin's shock, Baelfire shouts had he been asked, it would have been to stay with his father. Bitterly, Baelfire contemplates the lost chance at being a family with him, though Rumplestiltskin says they still can, though his son storms out abruptly. ("Nasty Habits")
Eager to fulfill his promise, Rumplestiltskin puts his new found powers to use by bringing about an end to the ogre war by walking into the middle of battlefields and brokering a truce between the warring parties. However, while this good deed brings Rumplestiltskin reverence and respect, the powers of the Dark One have corrupted his mind, causing him to continually hurt people and seek more power for fear that he would not be able to protect Baelfire from his enemies otherwise. As a downside, people begin to fear him due to his wealth and power, especially since Rumplestiltskin publicly demonstrates cruelty towards a peddler after Baelfire injuries his knee running into the man's wagon. Though Baelfire believes his father would not need so much power if he simply did not have any, Rumplestiltskin details the only way to rid himself of the Dark One's abilities is if someone killed him with the dagger. In a deal, Rumplestiltskin agrees to give up his powers, if there is way to do so without dying, if Baelfire can find a way. Baelfire comes back home with a magic bean given to him by the Blue Fairy so they can both go to a land without magic, thus making Rumplestiltskin without his powers. However, when the a portal is opened for them to jump into, Rumplestiltskin backs out of his promise to Baelfire, clinging onto his son's hand while the dagger keeps himself from falling in, until he finally lets go of Baelfire as the vortex closes. When he finally comes to terms with the fact his son is gone, Rumplestiltskin furiously calls the Blue Fairy and begs her to send him to Baelfire. She says it is impossible to do without any magical means, and accidentally lets it slip that a powerful curse can bring him to his son. From this point on, Rumplestiltskin vehemently swears to stop at nothing, even if it means sacrificing an entire world, to reunite with his beloved Baelfire. ("The Return")
Since Rumplestiltskin's loss of his son, the seer, now much older, appears before him once more and proclaims the future she foresaw for him many years ago has recently come to pass. With magical force, he demands information out of her about how to reach his son. Eventually, she allows him to take her powers so that he may learn to see into the future. By doing so, the burden of future sight is no longer in her hands. Just as the seer is drawing her last breaths of life, she sees into his future one last time. She speaks of how he find his son under the most unusual of circumstances, and a young boy who will be the key to the reunion. Alas, this boy will also be his undoing. Despite her warning, he doesn't see the boy as a true threat and decides to kill him when the time comes. ("Manhattan")
A time gap passes, and Rumplestiltskin is promised a magic bean by a man named William Smee. Rumplestiltskin agrees and promises the man eternal life in exchange, but if the bargain is not met, he will age him to dust. Before leaving the bar, Rumplestiltskin sees Killian Jones enter with his crew and stays to follow after them. In the alley outside the bar, Rumplestiltskin passes them and the pirates proceed to mock him. When Rumplestiltskin reveals himself, Killian recognizes him as the coward from his ship, but also as the Dark One. They begin a duel, with Killian nearly having his heart ripped out by Rumplestiltskin, until a very much alive Milah pleads on the pirate's behalf. He learns the truth of Milah's disappearance all those years ago, that the kidnapping was nothing but a cover story, and she willingly went with Killian because they fell in love. Rumplestiltskin is furious, but Milah offers him Smee's magic bean in exchange for both Killian's life as well as her own. They meet aboard Killian's ship the next day to seal the deal. Unable to hold back his inquiries, he questions her judgement in leaving their son behind. Milah admits to feeling guilty about her choice, which she made while miserable in the marriage with Rumplestiltskin. As the argument heats up, she denies ever loving him, causing Rumplestiltskin to rip out her heart out of rage. While Killian cradles a dying Milah in his arms, Rumplestiltskin crushes her heart to ash. Then, he procures the magic bean by cutting off Killian's clenched left hand. Though Killian stabs him with a hook, it has no effect on Rumplestiltskin, who departs unharmed. When he finally checks the severed hand, he discovers the bean is missing. ("The Crocodile")
In a deal with Jiminy, who wishes to be free of his parents, Martin and Myrna, Rumplestiltskin gives him a potion to transform them into another form. However, Jiminy's parents switch the potion to give it to a village couple, Stephen and Donna, which converts them into puppets. Afterwards, the puppets are retained in Rumplestiltskin's possession within his castle. ("That Still Small Voice")
Driven by a vision through his future-sight, Rumplestiltskin approaches a miller's daughter, Cora, who is stuck in a room with straw after boasting she can spin straw into gold. King Xavier will give her death if she does not do it. Rumplestiltskin claims that he can help her, but for a cost. He shows Cora that he can spin straw into gold, and states that he will help her out if she gives him her first-born child, who will have great importance in the future he foresees. She agrees, but only if he teaches her how to spin straw into gold. He instructs that the key to making magic work is to give into the rage of emotion she feels at her worst moment. They bond over their similar, humiliating experiences. Her anger channels into magic, and turns the straw into gold. After Cora wins the hand of King Xavier's son, Rumplestiltskin visits her on the day before the wedding where they share a passionate kiss. Despite being fifth-in-line once she marries the prince, she has a change of heart and would rather have the genuine love Rumplestiltskin has given her. He decides to change the deal so any child they have together will be his. Cora readily agrees, but wants to learn how to rip out a heart, so she can have revenge on King Xavier. Following this lesson, they settle on meeting under a tree in the castle courtyard after Cora has extracted King Xavier's heart in a box, and then they will run away together. When she finally arrives, Cora goes back on their agreement as power is more important to her than love. Puzzled, he asks whose heart is in the box. Saddened, Cora admits it is hers as it is necessary to remove the love she has for him to focus on obtaining power. Infuriated at the betrayal, he demands payment for their deal, but Cora reminds him of the changed contract, and any child she has will never be his. ("The Miller's Daughter")
In another kingdom, ruled by King George, he finds himself unable to bear an heir after his wife is cursed to be barren. Rumplestiltskin finds a farm where a commoner, Ruth, has recently given birth to twin boys. Granted permission by both her and her husband, he takes one of the children to be raised as King George's heir in exchange for keeping the farm afloat with monetary support. ("The Shepherd")
One evening, Rumplestiltskin is summoned by Regina, the daughter of Cora, when she accidentally says his name out loud from her mother's spell book. He exhibits knowledge about who she is as their families know each other in the past and future. To his surprise, Regina is a sweet-natured woman who doesn't wish to hurt anyone, particularly when he suggests she can kill Cora. He shows Regina magic mirror to another world and tempts her into getting rid of Cora with a simple push into it. On the day of the wedding, Rumplestiltskin manifests inside the mirror reflection to beckon Regina into going through with their plan, to which she obeys. Now free of her mother, she returns the spell book to Rumplestiltskin on her way out of the kingdom. Though Regina insists she doesn't need magic, he continually prods her over how it felt using magic. She admits, with much hesitancy, that she loved it, but has fears of turning out like her magic obsessed mother. Rumplestiltskin promises that is entirely up to her, and takes Regina under his wing as a magic protege. ("We Are Both")
To start with, he instructs Regina how to conjure a rock, which she has difficulties learning. Rumplestiltskin later spies on her mastering this technique, but upon closer look, it is actually a red-haired woman donning Regina's clothes. The woman, Zelena, claims to be Cora's first-born child; something he refuses to believe until testing her genetics. Surprised by the unexpected, Rumplestiltskin teaches her magic, as he did with Cora, by helping her channel rage into power. As a cooling down period after exerting this much magical force, she is taught to think of a happy memory. When Zelena asks for an example, he tells her of his time growing up with spinsters who baked him meat-pies. After the lesson, she makes him a meat-pie as thanks, but he cannot stay since Regina still needs his help learning magic. At this, Zelena reacts with intense anger and repeatedly insists she should be the one casting his curse instead of Regina, to which he points out that her jealousy is literally turning her skin green. Realizing the potential danger, Rumplestiltskin masquerades as Regina to bait Zelena, who tries to kill her half-sibling. He disqualifies her from casting his curse since one one of the spell's main ingredients is the thing she loves most—him—and that makes her too dangerous. However, Rumplestiltskin is quick to change his mind after Zelena mentions she has a pair of slippers that can take him to a Land Without Magic. Zelena scornfully rejects his offer, and before disappearing, she promises that next time he will choose her. Soon after, Regina succeeds in conjuring the rock, which pleases Rumplestiltskin so much he dubs her his "best pupil". ("It's Not Easy Being Green")
The lesson moves onto teaching Regina to manifest a ball of fire. After he demonstrates, she tries to mimic him, but has problems keeping the fire from burning out. ("Kansas")
Continuing to train Regina in the dark arts, Rumplestiltskin has her learn how to rip out a horse's heart, but she refuses to do it. Annoyed by her hesitation, he tells Regina to figure out what is holding her back. He discovers she is still pining after her dead fiancé, though it is not possible to bring someone back with magic. Instead, he does a bit of research by travelling to the Land Without Color to witnesses a doctor, Victor Frankenstein attempting to retrieve his brother from the dead. They come to a deal for Victor to teach him knowledge on revival while Rumplestiltskin leaves behind a horde of gold for him as payment. He comes to Victor again after the doctor's failure at revival due to scorching his brother's heart. Rumplestiltskin guarantees him a stronger heart if he will help fake a failed attempt to restore Regina's deceased lover. The doctor agrees, and Rumplestiltskin returns to the Enchanted Forest to turn Regina away from magic lessons since she can't let go of the past. At the same time, Rumplestiltskin procures items from a world traveler, Jefferson. Unknown to Regina, the two are working together to push her to call on Victor to resurrect her fiancé. Victor follows the terms of Rumplestiltskin's deal to crush Regina's hopes of regaining her past. Directly after, Rumplestiltskin takes on a new magic apprentice, Trish, though Regina cuts the lessons short by tearing out and crushing the girl's heart to prove to Rumplestiltskin she is ready for the dark arts. Satisfied with the end result, Rumplestiltskin takes her back, and in secret, gives Victor a heart as promised. They have a disagreement about the usefulness of magic, though Rumplestiltskin is quite certain Victor will discover magic is indeed beneficial. ("The Doctor", "In the Name of the Brother")
Regina resumes her magic lessons with Rumplestiltskin, but does not show up as planned for one session. That night, while she is dining alone, he materializes in the seat across the table from hers. Regina voices concerns about continuing the lessons as she doesn't want her own future to end up like his, and when prompted, goes on the detail the unhappiness in her life. She talks about being Queen as well as feeling like a prisoner in a castle, having a husband whose only focus is on his dead wife and young daughter. With no freedom, she finds life intolerable. Rumplestiltskin interjects that leaving this life is not possible even though Regina thinks there are choices in having love or darkness. He states what she doesn't know is that darkness is what will consume her. Upset at his words, Regina orders him to leave. Instead, Rumplestiltskin explains further that once the darkness has started to eat away at her, it will progress until she is swallowed whole, and there's no way to fly away from fate. Before leaving, he sets up lessons for tomorrow and stresses she must bring the only thing inside herself, which is simmering rage. ("Quite a Common Fairy")
Some time later, Rumplestiltskin has amassed considerable wealth and a castle of his own, but grows lonely and sought someone to take care of his estate. Summoned by Sir Maurice to protect his town from a horde of ogres, Rumplestiltskin makes a deal to protect the kingdom in exchange for Maurice's daughter, Belle, to live in his castle forever as a caretaker. ("Skin Deep")
Annoyed at Belle's nightly crying sessions due to missing her family, he bursts into her cell to conjure a pillow for her. Though she thanks him, he remarks it's not for sleeping, but to muffle her cries so he can concentrate on his spinning. Suddenly, they discover a hooded thief with a bow and arrow stealing a wand. Caught in the act, the thief slips off his hood and shoots an arrow, which he claims always finds its target, at Rumplestiltskin. The Dark One dodges until the arrow hits in square in the chest, but a moment later, he surprises the thief by pulling the shaft out with no damage done to himself. Taking the thief as a prisoner, Rumplestiltskin flogs and tortures him on a daily basis. After one grueling session, he leaves the castle and returns to find Belle already set the thief free. Furious, he makes her tag along so she can watch him kill the thief. During the carriage ride, Belle tries to talk him out of murdering the thief so people will see he is a man, not a beast. She believes he loves something more than power. Rumplestiltskin agrees, but cackles that he loves his things most of all. They get out on a road to meet the Sheriff of Nottingham as Rumplestiltskin asks him for information on the owner of the thief's bow. The Sheriff is unwilling to say anything unless he can spend a night with Rumplestiltskin's "wench", referencing Belle. Rumplestiltskin refuses, and when persistently pressed, he rips out the Sheriff's tongue as leverage for him to spit out information. After shoving the tongue back in, the Sheriff tells him the thief's name is Robin Hood and where to find him. They spy Robin Hood waiting near a tree and then watch him run to the road when a carriage with a sickly woman lying in the back of the vehicle approaches. Robin Hood uses the wand to heal the woman back to health, and Belle is ecstatic he stole the wand for a good purpose. Rumplestiltskin ignores this and traps Belle in the ground as he readies his arrow. However, Belle pleads, upon seeing the woman is pregnant, that killing Robin Hood will make the child fatherless. Rumplestiltskin loses his will to kill as he is reminded of his own son. He purposely loosens the arrow onto the carriage, which scares off Robin Hood and his companion. When they get back to the castle, he brings her to a large library room, which pleases Belle very much. He denies the room is for her reading satisfaction, and only needs her to make everything spotless. Even so, Belle can guess he did it for her, and states there really is good in his heart. ("Lacey")
On the night of Baelfire's birthday, Rumplestiltskin sadly lights a candle in his honor. Belle walks in on him and though she apologizes, he coldly orders her out of the room. Instead, she walks up to set a basket of flowers on the table. He gives her a second warning, but she still doesn't leave. Belle notices a shawl sitting nearby and realizes he must have been using the candle in remembrance of someone. She gives her condolences, even asking how old would he be, but Rumplestiltskin states this person is not dead, and only lost. He admits it is this person's birthday—without using Baelfire's name—and expresses regrets for his own past actions that tore away their chance of happiness. Belle proposes it's not too late. Though Rumplestiltskin hopes for the same, he thinks his own ending won't be a happy one. ("Going Home")
The Queen, Regina, vents her frustration to Rumplestiltskin about how the citizens of the kingdom don't love her, and they only want her stepdaughter Snow White as Queen. She proposes he teach her a spell to disguise herself so she can fool Snow White and get close enough to kill her. Rumplestiltskin doubts Regina can do it because it took her mother, Cora, a month to learn that spell, and Regina would only be able to change her hair color in a week's time. Regina wants to use any means, so she asks him to cast the spell instead. Because Rumplestiltskin is the one casting the spell, Regina will have no control over when the disguise comes off, and she will be magic less. Another deal is bargained, and in exchange, he wants her to cut off monetary ties with King George of the neighboring kingdom. She wonders why, and Rumplestiltskin retorts he needs the king bankrupt, but it is none of her business. By casting the spell, he turns Regina into a peasant, although to her own eyes, she still looks like herself, but to other people, she has an entirely different face. He warns amongst the commoners she may not like what she will hear them say about herself, though Regina insists it will not matter. Though Rumplestiltskin previously told Regina to call out his name whenever she wants the disguise to come off, he does not respond after she calls twice. When she storms into his castle, he jokingly remarks that she's come to be his maid, though it is a jest she does not find amusing and wants Rumplestiltskin to take off the disguise right this instant. As Regina gazes into the mirror, she is annoyed and ponders if Rumplestiltskin just wants her to admit he was right about what the commoners—that they will never love her. She sadly states it is true, to his absolute glee. He asks what she will do, and she vows to punish them all. Finally, he reverts her back to normal as Regina embraces herself as the Evil Queen. ("The Evil Queen")
Some time later, he is summoned to king's court, where King George begs him to bring his son, who has been killed in a tournament, back from the dead. Rumplestiltskin admits not even magic can bring back the dead, but tells the King that Prince James has a twin who can take his place. In return, he demands the location of King George's family fairy godmother as payment for getting the other twin, which King George reluctantly gives into. Rumplestiltskin goes back to the farm to collect the other twin, David, and convinces him to masquerade as King George's son. ("The Shepherd")
Outside his castle, Rumplestiltskin sights his most hated enemy, Hook, and immediately begins suffocating him until the pirate's companion, Emma, tells him of how he will cast a powerful curse, which she breaks, and and will lead to his reunion with Baelfire. To keep the past unchanged and ensure the future, Emma and Hook need his help to organize a destined first meeting between Prince Charming and Snow White. After the trio enter his castle, Belle walks in to greet him and ask if he needs anything. Strangely, Emma knows Belle, claiming Rumplestiltskin mentioned her, though he did not. Rumplestiltskin shoos his maid away, and then hears Emma remark about the irony of him and Belle later falling in love, which he thinks is preposterous. Emma shows him storybook images of Prince Charming and Snow White's future, but the pages are blank. He states that they can find Prince Charming, under the alias Prince James, at King Midas' castle. Through a crystal ball, they see Snow White seeking passage onto Black Beard's ship, but she doesn't have enough money. Emma theorizes Snow White must steal Prince Charming's ring to set the past back on track. After motivating Snow White to do so, Rumplestiltskin explains to Emma and Hook that he has a wand, which can recreate a portal, as it can replicate any magic that has ever been wielded. Before the pair sneak into King Midas' castle to check on Snow White, Rumplestiltskin casts a spell to disguise them as different people. Back in his castle, the Dark One discovers the wand can only open a portal by those who traveled through it. He prepares a forgetting potion to erase his memories of the future just as the twosome, with another person, arrive back. Rumplestiltskin explains the portal issue and hands the wand to Emma. Intending to "protect the future", he traps them in his vault, but Emma uses the wand to open a portal. Rumplestiltskin grabs onto her and demands to know what happens when he finds Baelfire. Emma states that his son forgives and loves him, but dies in order to save everyone. Shocked, he insists the future can be changed, but Emma warns that doing so may make things worse. She urges him to drink the potion, which he does while letting go of her. After she disappears into the portal and it closes, Rumplestiltskin, his memories erased, picks up the fallen wand and teleports out of the vault. ("Snow Drifts", "There's No Place Like Home")
After Belle has been his maid for several months, he allows her to go into town on the pretext of fetching him straw for spinning gold. In actuality, he expects to not see her again once she leaves; assuming she has the opportunity to finally leave on her own. Against Rumplestiltskin's assumptions, as well as her own, Belle returns to the castle to give him true love's kiss, causing him to begin reverting to human form. Shocked by her actions, he incorrectly believes Belle is working with the Queen when she stutters about learning from a woman that kissing him would break his curse. In a fit of anger, Rumplestiltskin locks her in his dungeon and later casts her out of his castle with the claim he values power above everything else. However, Belle challenges Rumplestiltskin, declaring that despite all his efforts to be powerful and feared, he is still a coward at heart for not being able to accept someone could actually love him, in the end power will only give him, "an empty heart and a chipped cup." Then, she leaves the castle for good. Some time after, the Queen visits Rumplestiltskin and goads him about his ex-maid's torturous fate at the hands of her father, who believed she had been sullied by the Dark One's evil ways, and sought out priests to cleanse her in a locked tower, which ended with Belle committing suicide. Visibly shaken by this knowledge, Rumplestiltskin calls the Queen a liar and tells her to leave. Left alone in his grief, he replaces a golden chalice on a pedestal with a teacup Belle had chipped on her first day as his caretaker; the only memento he still has of his lost love. ("Skin Deep")
To find the Fairy Godmother, whose wand he desires, Rumplestiltskin goes to the family manor of a maid named Cinderella. Interrupting the Fairy Godmother's wish granting session, he kills her and takes the wand as a shocked Cinderella watches. He convinces the maid to make a new deal with him instead—she can attend the royal ball, but will owe him something "precious". Cinderella agrees, signs the contract, and hurries off to the ball. ("The Price of Gold")
Some time later, he meets with Snow White, who wants him to give her something to forget the man she loves, Prince Charming. Rumplestiltskin plucks two hairs from her head; using one to create a forgetful potion for her and keeping the other as payment. ("7:15 A.M.")
After Snow White drinks the potion, she only cares about exacting vengeance on the Queen. One of the seven dwarves, Grumpy, drags her to Rumplestiltskin hoping he can fix it, but it's not possible. Instead, he sends Snow White on the road to becoming a murder by giving her Robin Hood's old bow to use on the Queen. On the same day, Prince Charming is ensnared into a deal with Rumplestiltskin in exchange for information on Snow White's whereabouts. Rumplestiltskin takes Prince Charming's cloak as payment, but in truth, he picks off a strand of the man's hair. Entwining the strand with Snow White's hair, he creates the elusive and rare form of true love in a bottle. ("Heart of Darkness")
Rumplestiltskin has further success in creating the Dark Curse and places a single drop of true love on the spell parchment as "a little safety value". Meanwhile, he approaches a struggling Prince Charming in the Infinite Forest, who can't seem to find his way out to reach Snow White. He steals Prince Charming's ring, enchanting it to glow when near Snow White, and suggests another deal. Prince Charming vehemently refuses, and draws his sword. Rumplestiltskin humors him with a fight, but with his powers, he easily defeats Prince Charming, and informs him they're after the same thing—he and Snow White being together. Then, he shows Prince Charming his true love potion. When asked what he knows about true love, Rumplestiltskin describes his own past love as "a brief flicker of light amidst an ocean of darkness", though she died. The fragile nature of true love combined with its unequaled power, the ability to break any curse, is why Rumplestiltskin wants it to be protected. He instructs Prince Charming to hide the potion "inside the belly of a beast". After Prince Charming successfully puts the egg inside the body of a dragon, he surfaces at a beach shoreline near Maleficent's castle. Rumplestiltskin hands over the ring, and then uses his powers to give the latter a princely outfit to match with the occasion. Prince Charming asks why Rumplestiltskin is helping him so much. Mysteriously, the Dark One states he is a fan of true love, and what it creates. ("A Land Without Magic")
Having secured and enacted the deal with Prince Charming, Rumplestiltskin returns to his castle. While spinning gold at his leisure, he is visited by Prince Charming, who wants to bargain in helping a now curse-less Snow White to find the motivation to fight against the Evil Queen for the kingdom. However, Rumplestiltskin has nothing to give him. Instead, Prince Charming comes up with a plan of his own and manages to strengthen Snow White's resolve in battling for the right of the throne. Snow White, having the impression all this was possible because Prince Charming made another deal with Rumplestiltskin, decides she wants to pay the price of magic. In the forest, she summons the Dark One to explain her intention to reimburse him for his services rather than let Prince Charming do so. Rumplestiltkin inquires about the sword Snow White is holding, which she says is the legendary Excalibur of Camelot, and having pulled it out of proves herself to be true claimant to the kingdom. In disbelief, Rumplestiltskin shows her the sword is nothing but a forgery by using magic to dissolve it into dust. After spilling the truth that no deal was made between himself and Prince Charming, he rips a necklace from Snow White's neck as payment for wasting his time. ("Lost Girl")
Soon, a war ensues between Prince Charming and Snow White against the combined armies of the Evil Queen and King George. At long last captured, the Evil Queen is sentenced to death by the kingdom's war council, though Snow White is resentful of the decision. At the execution, Rumplestiltskin and many other citizens gather to watch, but at the last moment, the Evil Queen is allowed to live on Snow White's orders. In the evening, he gives Snow White an enchanted knife to test on an imprisoned Evil Queen to see if she is capable of changing her murderous ways. The Evil Queen fails the test by attempting to stab Snow White with the knife, which is magically rendered ineffective. In addition, whoever uses it will never be able to harm Snow White or Prince Charming in the Enchanted Forest. The Evil Queen, banished to elsewhere, is visited by Rumplestiltskin at a later date. She is deeply upset at never having the chance to kill her enemies again, though Rumplestiltskin stresses a particular caveat of the enchantment--they cannot be harmed in this land, but can in others. His words help her recall the effects of the Dark Curse, and she hurries off to Snow White and Prince Charming's wedding to announce her intentions of using it to destroy their lives for good. ("The Cricket Game")
Since Cinderella's deal with Rumplestiltskin, she captures the attention of Prince Thomas at the royal ball and they soon marry. During the wedding party, Rumplestiltskin shows up just long enough to claim his "precious" price from Cinderella as her firstborn child. Many months later, he meets with Cinderella again, whereupon she tells him she is due to have twins and wants to make a new deal. At first he does not believe her, but after warning Cinderella about the consequences of using magic against him, he eventually signs the contract with a quill filled with squid ink, which paralyzes him. Grumpy and Prince Charming load Rumplestiltskin up into a cart to take him away to prison, but Thomas mysteriously disappears. Upon confrontation, Rumplestiltskin states that Thomas will never return unless he receives her baby. Then, he is carted away to his prison in the dwarves' mine. ("The Price of Gold")
When Snow White becomes heavily pregnant, she also grows even more concerned about the threat of the Dark Curse from her former step-mother. Snow White and Prince Charming go to Rumplestiltskin, the only man powerful enough to counter the Queen's magic. Their escort warns them not to tell him their names, because it will give him power over them, but Rumplestiltskin already knows who they are. Rumplestiltskin agrees to give them information in exchange for their unborn baby's name, to which Snow White agrees, in spite of the guard's earlier warning. He tells Snow White and Prince Charming that the only thing that can save all the people in the land from the curse is their unborn child who will come back to save them all on her twenty-eighth birthday. As they turn to leave, Rumplestiltskin asks for their child's name. After a moment of hesitation, Snow White states the child's name to be Emma. To help himself to remember this vital piece of information, he repeatedly writes her name on a piece of parchment using squid ink. ("Pilot", "Queen of Hearts")
The Queen attempts to fulfill plans to use the Dark Curse, but her first attempt at casting it fails. She visits Rumplestiltskin to find out why, and his price for this information is to receives riches, comfort, and influence in his life once the curse takes effect, and that if he comes to her for any reason, she must give him anything if he uses the word "please". After the Queen agrees to this, Rumplestiltskin tells her that she must sacrifice the heart of the thing she loves most for the curse to work. ("The Thing You Love Most")
On the day the Dark Curse is cast, he expectantly waits for it to take effect. The Queen materializes outside his cage to gloat about her success with the Dark Curse and boasts at the knowledge he, like all others will be affected by it, will soon lose their memories of everything. He relishes in asking her how it felt ripping out her father's heart for the curse to work, but she doesn't answer as it is of little importance. Rumplestiltskin can tell despite her triumphant front, she is still unsatisfied with something. He stresses that Prince Charming and Snow White's child will foil her curse, to which the Queen plans to get rid of the baby. Additionally, Rumplestiltskin hints that now she has hole in her heart and will feel the need to fill it in the future. The Queen doesn't take his prophecy seriously, though he shouts she has underestimated the price of magic and will come back for his help someday. Soon after, the curse takes Rumplestiltskin and many other inhabitants of the Enchanted Forest to another land. ("Save Henry", "Pilot")
For events occurring after the casting of the first curse, see Mr. Gold.
Before Second Curse
Rumplestiltskin's body and his dagger are recreated from a black liquid, when his son, Neal, uses a key to open the vault of the Dark One. As an unexpected cost, which Neal is not aware of, he dies while Rumplestiltskin is revived. As his son perishes, Rumplestiltskin grabs hold of him as well as the dagger. However, he is not able to grip both at the same time, and the Wicked Witch snatches the dagger. Unwilling to let Neal perish, he absorbs his son into his own body to keep him alive. Enslaved to the Wicked Witch's orders via the dagger, she orders him to kill Belle. Just before he does, Lumiere entraps the Wicked Witch in flames. Belle flees with Lumiere in tow while Rumplestiltskin is forced to stay behind. ("Quiet Minds")
Imprisoned in a cage in his own castle, Rumplestiltskin busies himself with a spinning wheel. Belle, Prince Charming, Snow White, Robin Hood and Regina break in to ask him how to defeat Zelena, but he responds with gibberish and veiled speech. However, when Belle approaches, he recognizes her and provides information about the banished Good Witch of the South, Glinda, who may be able to help them. His only clue to her whereabouts is a door that can only be entered by the pure of heart. Shortly after, Zelena, discovering Snow White cast another Dark Curse to find Emma, drops a potion into the mixture to erase everyone's memories of the last year in the Enchanted Forest. Before the curse spreads, she drinks a substance to retain her memories, and then passes it to Rumplestiltskin. She gives him the option to remember losing his son, or be foolish enough not to take the potion and forget everything. Left alone, Rumplestiltskin chooses to ingest it; believing that with pain is power, but also vengeance. As he lifts the vial to his lips, Neal breaks free. While Rumplestiltskin is passed out, his son writes a note to Hook asking him to give the potion to Emma, and he then attaches it to a messenger bird. With his last bit of strength gone, Neal returns to his father's body; causing Rumplestiltskin to awaken. ("A Curious Thing")
For events occurring after the casting of the second curse, see Mr. Gold.
According to Robert Carlyle, Rumplestiltskin is three-hundred years old by the time the Dark Curse is cast.
Robert Carlyle revealed in an interview that it takes approximately two hours to dress him in Rumplestiltskin's costume, twenty minutes of which is spent on his boots. He also revealed that it takes about one hour to remove the costume.
His spoken phrase, "Tick-tock, dearie, tick-tock!", is a reference to the crocodile who swallowed a clock from J.M. Barrie's "Peter Pan".