Prince Charming is born with the name David, to a poor peasant family, with a twin brother. Rumplestiltskin comes to their farm when he is an infant and tells his parents that the barren king and queen of their country need a child, and they will be paid handsomely if they give one of the twins to them. The parents choose to give away Prince Charming's twin, James, who becomes a prince, while they keep David. ("The Shepherd")
As a young boy, David overhears his parents quarreling, for the umpteenth time, about his father's drinking problems. This time, his father expresses a sincere desire to change for his son's sake, promising that by the time he returns from a two week run to haul farm supplies, that his alcohol dependency would be gone. Pleased, David looks forward to the fourteenth day when his father will finally return home. Tragically, he and his mother are notified that his father, although sober for thirteen days, became drunk at a tavern on the fourteenth day and died after falling into a ravine. The death has a significant influence on David, who understands how much his father wanted to change but ultimately could not, as he begins to believe some battles simply cannot be beaten. ("White Out")
Years later, David becomes a shepherd, but he and his mother face troubles on the farm when a warlord, Bo Peep, badgers them for money. He acquainted with a man from Arendelle named Kristoff. One day, a woman, Joan, arrives stating she knows his name from someone from Arendelle. Seeing as Kristoff is the only person he knows from that place, David guesses she knows him, too. Revealing little, except that she is on a "secret mission", Joan asks permission to stay on his farm for the night. Noticing the ring on her finger, David recognizes that she must be Kristoff's fiancé. As they talk, Bo Peep arrives to collect payment. Since farm business is poor, their earnings are not enough, so Bo Peep sets a deadline. She warns that if they cannot pool the money by tomorrow, the farm is hers. Additionally, she brands them, using her shepherd's crook, and promises that they will become her slaves if the deal is not met. Joan, believing David must defend himself against this tyrant, teaches him how to sword fight. While she thinks he is making progress, David gives up after being unable to beat her during training. He argues that some battles can't be won, and the most important thing for himself and his mother is survival. Joan insists that surviving is not living, and she elaborates by telling him about how her sister tried to solve problems by running away like him. When she claims he knows nothing about loss and is only afraid of it, David recalls how his father's death due to alcoholism shaped his beliefs. Despite his pessimism, Joan offers to continue training with him tomorrow. The next morning, David enters the barn where they promised to meet, asking Joan to leave instead of trying to help him, when Bo Peep makes herself known. Holding out Joan's pendant, Bo Peep threatens him with no choice but to pay her. Choosing to fight, David takes on two of her henchmen before dueling with the warlord herself. He tricks her, causing her sword to be embedded in a pillar, and then corners her at sword-point. After tying her to a pedestal, he uses the shepherd crook to find Joan in a shed. After returning the pendant, David explains his decision to fight due to realizing that surviving means being able to move on from a life he doesn't want. Before Joan leaves, David gifts her a steed, which belonged to his father, as he no longer needs a reminder of the past. ("White Out")
Some after, Rumplestiltskin persuades David into being a replacement prince for his deceased brother, James, and in return, the farm will be saved. He agrees to the plan for his mother Ruth's sake. As Prince James, he has to kill a dragon for King Midas. While meeting knights who will be accompanying him on the journey, David learns they will slay the dragon so he can take the credit. Atop of the dragon's lair, all but one knight perishes. David manages to save him while tricking the dragon and cutting off its head. Afterwards, King Midas is so pleased with the results that he offers up his daughter Abigail's hand in marriage. As David moves to reject the notion, Prince James' adoptive father King George pulls him aside to threaten to harm the farm and his mother if he does not comply. King George wants the alliance as well as the lands and riches it will bring, so David must agree to the marriage. David returns to inform Ruth of the change of plans, which sadly means he has to continue living the ruse of Prince James and marry Abigail, so it's not possible to see his mother ever again. As a parting gift, she gives him her own wedding ring, so that he can give it to the woman he loves. Returning to his role of Prince James, he and Abigail take carriage ride on the scenic route towards King Midas' palace to begin the wedding preparations. ("The Shepherd")
During the carriage ride to the castle, David gets a dose of Abigail's quarrelsome personality. When the road is blocked by a fallen tree, he exits the carriage, leaving his mother's ring behind, to examine the damage. David recognizes the trunk markings as someone's deliberate action to bring the tree down, but is suddenly alerted to Abigail's scream as a thief escapes with his ring. After chasing down the thief, he wrestles the bandit to the ground and flips him over; only to find out he is actually a she. He lets down his guard in surprise, to which the woman hits him with a rock and flees on his horse. David vehemently shouts that he will find her again. Later, he discovers the woman is Snow White, a wanted criminal the Queen is been seeking. He also sets a trap outside Snow White's makeshift home and captures her in a net. While he laughs at her predicament, she sarcastically dubs him "Prince Charming". He threatens to turn her into the Queen, but won't if she returns his ring. Snow White admits to already selling the ring, but left little choice, she agrees to help him. On their way, he takes her vial of fairy dust, which she is planning on using on the Queen. When questioned about her wanted status, she alludes to having destroyed the Queen's happiness. At a stream, Snow White requests a sip of water, but when he allows it, she clocks him and runs away. He catches up in time to save her from one of the Queen's knights. In gratitude, she agrees to the Troll Bridge and retrieve his ring. The trolls suspiciously search through Prince Charming's things and see the wanted poster. When they attack, he is entrapped while Snow White escapes. She returns to throw fairy dust on the trolls, transforming them into bugs, and they leave with the retrieved ring. As the two part, Snow White jokingly tries on his ring, though she states it's not her style. With the terms of their agreement satisfied, they both leave in opposite directions. ("Snow Falls")
During the carriage ride, a fallen tree blocks the road and David discovers it was deliberately placed there. Fearing an ambush, he and the guards quickly arm themselves, but the assailant is gone. As they near King Midas' castle, David is surprised by the exterior's gold encrusted walls, though Abigail says he'll stop noticing after a while. During the engagement party, he offers to dance with her, but she complains about wearing uncomfortable shoes. David proposes fetching another pair, though his wife-to-be sarcastically calls him her hero and walks off. Heading upstairs, he stops someone from stealing his ring. Upon flipping the bandit over, he realizes the thief is a "girl". She corrects him, calling herself a "woman", and then hits him. The woman escapes, though David angrily shouts that he will find her again. Later, he learns out she is a wanted murder, Snow White, and he catches her in a trap where she spitefully dubs him "Prince Charming". He asks for his ring, though another prince, Charles, states it is with his princess, Leia, who is now the Queen's prisoner, so they must save her first. On the journey to the Queen's castle, Prince Charming toys with Snow White's vial of fairy dust, which she is saving to turn the Queen into a bug. She claims the Queen hates her for ruining her life, and the charges on the wanted poster are false. Snow White enters the castle first, but tells the princes to wait until nightfall. To Charles, Prince Charming describes his marriage as a business transaction, and he had hopes of marrying for love. A friend of Snow White's, Red Riding Hood, transforms into a wolf to help break into the prison. They regroup with Princess Leia and another freed prisoner, but witness Snow White's execution. However, Prince Charming realizes she isn't dead, but simply turned herself into a bug with the remaining dust. With the Blue Fairy's help, she reverts to human. The next morning, Snow White secretly makes off with the ring, though he catches her at the Troll Bridge. When he is trapped, she saves him by threatening to turn the trolls into bugs. At their parting, Snow White jokingly tries on his ring, but declares it's not her style. With the terms of their agreement satisfied, they both leave in opposite directions. ("Snow Drifts", "There's No Place Like Home")
A few days after, the engagement party is held, but Prince Charming retreats into his room in a restless and brooding mood. His behavior does not go unnoticed by King George, who is aware Prince Charming is in love with someone else and threatens to burn down the farm if he does not marry Abigail. Despite the severe warning, Prince Charming writes a letter to Snow White, declaring his genuine feelings for her and asks that, if she feels the same, to meet him at the castle so they can run away together. When they finally meet in person, Snow White affirms she does not love him, and it would be better if he is with someone like Abigail who could. ("7:15 A.M.")
Although heartbroken, Prince Charming cannot bear to marry a woman he does not love and runs off from the impending wedding. During this, he is accosted by some henchman, and believes they are King George's men until being set free by them. In actuality, Abigail sent soldiers after Prince Charming, as she wanted to get to him first before King George. She, too, does not wish to marry him. When he inquiries about her reason for helping him, Abigail takes Prince Charming to a shrine with a golden statue of the man she loves, Frederick, who became immobile after being touched by her father's curse. Her many attempts at true love's kiss have failed, though there is the magic water of Lake Nostos rumored to restore something once lost and is guarded by a ghastly creature. He decides it's in his own best interest to change the wretched circumstances so Abigail and Frederick can be together. She protests against this, but Prince Charming claims succeeding will lift Abigail out of her own misery, and if not, then the misery of failure will be his own. They go together to the entrance of the lake and come across an shrine that people have used to ask for the creature's mercy, but he ignores this and goes straight in alone. As he is scooping up some of the water, a Siren in the form of a beautiful woman rises from below the surface. Prince Charming is not tricked by her alluring appearance until she turns into the one person he desires most—Snow White. Though nearly seduced, Prince Charming shakes out of the stupor upon realizing this carbon copy of Snow White is no replacement for true love, to which she tries to drown him. Underwater, he grabs a dagger and stabs the Siren to death. With the mission complete, he goes back to an ecstatic Abigail and gives her the water. She pours it over Frederick's head as the gold melts off and the long-separated couple joyfully reunite. Abigail introduces the two men to each other as Frederick offers Prince Charming his utmost gratitude. In return, he receives a horse from them and uses it to find Snow White's newest hideout. Instead, Prince Charming meets Red Riding Hood, who explains Snow White went to meet with him and never came back. He professes determination to reach Snow White and convince her that they belong together. This doesn't make sense to Red Riding Hood, as she clearly remembers Snow White left intending to break up Prince Charming's wedding because of her love for him, unless something changed. He realizes King George ruined everything just as the man himself arrives on horseback to close in on them. Prince Charming and Red Riding Hood flee for safety. ("What Happened to Frederick")
They camp out for the night, but are found by King George's men. While Prince Charming escapes, Red Riding Hood stays behind and takes care of the soldiers by shape shifting into a wolf. Continuing with the search on his own, he comes across a nude soldier who claims that Snow White stole his armor from him in order to kill the Queen. Prince Charming doesn't believe this, but investigates the matter after hearing Snow White recently went to Rumplestiltskin's palace. He is too late since she, afflicted by a curse since ingesting a memory potion, just left to kill the Queen. Rumplestiltskin swears that the curse, though it has rendered Snow White cold and heartless, can be undone with true love's kiss. Prince Charming agrees to give Rumplestiltskin his cloak in return for Snow White's location and arrives in time to see her preparing for the Queen's assassination. He tries to use true love's kiss on Snow White, to no avail, and is then knocked out and tied to a tree. The next day, he is freed of the binds with the help of the cricket, Jiminy, and rushes to take the hit of the arrow as Snow White fires at the Queen on the road. Prince Charming asserts that he would rather die than see her become evil. Touched, she kisses him, and returns to her normal self. They have a brief reunion just as King George's men capture Prince Charming, though she promises to rescue him. ("Heart of Darkness")
Prince Charming is brought out for an execution on King George's orders, which is stopped by the Queen. Rather than let him die, the Queen gives King George the gold he desired from the transaction with King Midas, and she takes away Prince Charming as a prisoner. The Queen comes into his cell to show him a cursed apple that she will make Snow White willingly eat and fall under a Sleeping Curse. He attempts to chase after her, but the cell door slams shut as she walks out. Through a mirror, Prince Charming sees Snow White break into King George's dungeon. When Snow White approaches him, only then does she realize Prince Charming is now in the Queen's hands. They place their hands against opposite sides of the mirror and converse, longing to be together, until the Queen interrupts to ask Snow White for an in-person meeting. Later, he feels bodily pain, and recognizes something bad must have happened to Snow White, but can do nothing. ("An Apple Red as Blood")
As two guards haul him out for execution, Prince Charming breaks free of them and flees, but is apprehended in the hallway by another one of the Queen's underlings. Surprisingly, the man shoots the remaining guard instead of Prince Charming, and then takes off his helmet to reveal himself as the Huntsman. He returns Prince Charming's sword and provides him with some provisions and a map out of the castle. The Huntsman explains how he gave up his own heart when disobeying the Queen's orders to kill Snow White, and asks that his sacrifice not be in vain. Prince Charming makes it outside, but is entrapped in the Infinite Forest by the Queen. He encounters Rumplestiltskin, who steals his ring and magically enchants it so the closer Prince Charming is to Snow White, the brighter it will shine. Prince Charming tries to take the ring back by force, but Rumplestiltskin bests him in a duel until he agrees to a deal. Rumplestiltskin hands him a bottled vial of true love encased in an egg to hide in the body of a beast. After wandering into a castle, Prince Charming is caught off guard when he meets a witch, Maleficent, who then turns into a ferocious dragon. While hiding behind a pillar, he notices Maleficent has a flap behind her ear that can fit the egg. Goading the dragon into chasing him, he eventually hops onto her neck and tosses the egg into the ear flap. An agitated Maleficent then shakes Prince Charming off her neck and spits flames at him, but he quickly jumps out a window. Landing in the water, he surfaces in time to see the dragon's head sticking out the window as she makes a futile attempt to huff fire at him. Making it to shore, Prince Charming receives the enchanted ring from Rumplestiltskin, and as an added bonus, the wizard also magically transforms his clothes into something befitting a prince and bestows a horse for his journey to Snow White. ("A Land Without Magic")
The ring takes him directly to his beloved, though she is already dead. With Snow White's body resting in a glass coffin, the seven dwarves mourn her death, but due to Prince Charming's pleas, they remove the cover to allow him a chance to say a final farewell. Bestowing a kiss to Snow White, he unknowingly triggers the effects of true love's kiss and revives her from the curse. ("A Land Without Magic", "Pilot")
Afterwards, they walk the beach coastline together as she inquiries how he found her. Flashing his mother's ring, he sinks to one knee and proposes to her. She happily accepts and the two decide take back the kingdom from the Queen and King George. ("A Land Without Magic")
During a rally, in which Snow White asks for the townspeople to fight alongside her for the throne, the Queen offers her a deal. When Prince Charming tries to intervene, the Queen gags him and then asks Snow White to give up her claim to the throne and go into exile. Snow White challenges this, so the Queen attacks a peasant girl. After the princess counters with her sword, the Queen teleports away and drops her hold on both the girl and Prince Charming. Reappearing, the Queen demands an answer by sundown tomorrow or for every day Snow White refuses, one of her subjects will perish. When Snow White decides to give into the Queen's offer, Prince Charming tries to gain support from the dwarves to convince her otherwise. Instead, they suspiciously believe the prince only wants the kingdom for himself and doesn't truly love her. Thus, he goes to Rumplestiltskin for a magical solution to bring out Snow White's courage, but even the Dark One states that true belief must come from within the person. Forging a fake Excalibur, Prince Charming shows Snow White the embedded sword, which can only be wielded by the kingdom's true ruler. After pulling it out, Snow White asserts to Queen that she won't give up the throne. Consequentially, the Queen chokes Grumpy as Prince Charming calms Snow White's panic by reminding her what the sword symbolizes. With renewed confidence, she charges at the Queen, who dissipates and reappears, as the sword cuts her. Then, Snow White declares she won't go down without a fight; forcing the Queen to retreat. Directly after, the dwarves finally accept Prince Charming just as Snow White confronts him about the fake sword. Prince Charming explains he never doubted she is the proper ruler of the kingdom, but wanted her to show the Queen the kind of courage he always knew was there. The two make-up with a kiss. ("Lost Girl")
With the Evil Queen out of the way, Prince Charming and Snow White begin laying down further groundwork for gaining back the kingdom. Receiving gets news from Red Riding Hood that King George has hired a powerful hit-man, Prince Charming offers to stay behind and hastens Snow White to run away to his mother's cabin. After the fight, he arrives at the cabin shortly before King George's army arrive to capture him. Although he emerges victorious, Ruth, worried about his well-being, runs outside and is shot by a poisoned arrow. Once Snow White and Lancelot rejoin the mother-son pair, they travel to Lake Nostos to find the cure for the wound caused by the poisoned arrow. However, the water have dried up some time after Prince Charming, came to the lake in the past and killed the guardian of the lake. Lancelot is able to find a small portion of water and brings it over to Ruth. She drinks it, but it has no effect. Knowing death is near, Ruth admits her only regret is not seeing her son get married to Snow White. Honoring her wish, Snow White asks Lancelot to perform a marriage ceremony. During the ceremony, Snow White drinks from chalice rumored to give eternal life while Ruth dies peacefully following the union. While lighting a candle to honor her, Prince Charming finds comfort in the fact though his mother is gone, he and Snow White can have a family one day. He shows her his mother's necklace, which has the ability to predict the gender of a person's future child. Unknown to him, King George previously cursed Snow White with barrenness, and as she begins to break the news to him, the necklace sways, proving the curse is broken. This is a result of Ruth's secret sacrifice of switching out the lake water into the ceremonial chalice for Snow White. ("Lady of the Lake")
Prince Charming and Snow White wage war against the Evil Queen and King George's forces. After King George's army falls, Snow White lures the Evil Queen into a conversation. The Blue Fairy freezes the Evil Queen with fairy dust and the war ends with her capture. In a discussion with the war council, they decide the Evil Queen's fate. Though Snow White is against killing the Evil Queen, but she is outnumbered, as the others believe death is a fitting punishment. At the execution, Regina gives her last regards to the public with a sorrowful speech, which turns into a vehement declaration as she is only sorry to have not caused more pain. As the executioner's arrows are fired, Snow White cancels the punishment at the last moment. While Prince Charming is adamant that Regina is simply too dangerous and will never change, Snow White believes there is still some good left in her. To prove it, Rumplestiltskin enchants a knife, incapable of harming the princess or Prince Charming, for Snow White to have when she goes to see Regina. The ex-Queen attempts to kill Snow White with the knife and is banished from the kingdom with the warning that harming anyone again will result in a death sentence. ("The Cricket Game")
With peace restored, Prince Charming and Snow White begin residing in the castle and hold a formal wedding ceremony as the kingdom's citizens gather in attendance. The Evil Queen crashes into the room just as the couple are joined in matrimony. As she walks up to them, Snow White shows no fear and unsheathes Prince Charming's sword as a threat. The Evil Queen announces her intent to have revenge on everyone by destroying their happiness. As she strolls out, Prince Charming chucks his sword at her, only for the Queen to disappear in puff of smoke. ("Pilot")
Following this, Snow White belligerently expresses anger at how the Queen ruined their wedding. Prince Charming convinces her to let it go, and she suggests they go to the old Summer Palace for their honeymoon. Once there, he attempts to have some alone time with her, but she has other ideas. Armed with the suspicion Snow White still wants to take down the Queen, he leaves the room and later blocks her on the road as she is sneaking off. She explains her plan to cut off the head of a being called Medusa, whose gaze can turn people into stone, and then use it on the Queen. Together, they venture into Medusa's home, where Prince Charming goads the creature towards him as Snow White readies her blade. Instead of severing the head, her sword shatters upon contact with Medusa's neck. As they attempt to flee, Prince Charming is turned to stone by Medusa. After catching the Queen spying on her current dilemma through a shield, Snow White realizes not letting go of her fears is ruining her life. After tricking Medusa into looking into her own reflection, the creature becomes stone while Prince Charming is freed. That night, she finally decides to stop worrying about the Queen's threats and wants to try having a baby. ("The New Neverland")
Riding back to the castle after their honeymoon, Prince Charming and Snow White discover the guards are asleep from a sleeping curse. Once they are past the gates, the couple meet Maleficent and her her associates, Cruella De Vil and Ursula, who reveal the Queen is planning to cast a curse that will affect themselves and everyone else. To defeat the curse, the trio want them to consult the Tree of Wisdom, a being that will only answer questions from two of the most valiant heroes. On the journey there, guards posted at a bridge refuse to let Maleficent and her companions cross. Before the royal pair can persuade the soldiers to relent, Maleficent morphs into a dragon and kills the guards with her fire breath. After camping out one night, Snow White and Prince Charming disappear towards the Tree of Wisdom without the others' notice. Once there, the pair put each of their palms on two rocks and ask their question, but both are ejected backwards. When the villainous trio arrive, Maleficent recognizes the tree refused them because Snow White is pregnant, and her child, although born of true love, has great potential to be evil. ("Unforgiven")
As a married couple, Snow White and Prince Charming a neighboring kingdom's royal wedding of Cinderella and Prince Thomas. During the wedding party, Prince Charming briefly dances with Cinderella and wishes her a happy marriage. While Cinderella is pregnant, he hears of her previous deal with Rumplestiltskin, which has resulted with the wizard demanding her first born child as payment. With the Blue Fairy and Grumpy, they hatch a plan to create an inescapable holding prison for Rumplestiltskin and have Cinderella paralyze him with a red quill infused with squid ink. Success follows, to which Prince Charming and Grumpy begin securing him in a cage for the journey to his prison when Cinderella runs up pressing Rumplestiltskin for answers about her missing husband. Rumplestiltskin gleefully acknowledges that Prince Thomas disappeared due to Cinderella's refusal to pay for their original deal, even though Prince Charming consoles her with a promise to find her husband. ("The Price of Gold")
While Snow White nears the end of her pregnancy, Prince Charming agrees to let her meet with Rumplestiltskin so she'll stop fretting about the Queen's warning at their wedding. She makes a deal to gain information about the Evil Queen's revenge, which Rumplestiltskin extracts from using foresight. He states that there will be a curse cast by the Evil Queen, and their only hope to break free of it is Snow White and Prince Charming's unborn child. Rumplestiltskin dubs their child the savior, who will save them all in twenty-eight years. Though Prince Charming believes their child is a boy, Snow White knows it's a girl. As payment for the information, she gives Rumplestiltskin the name of the child, Emma. Through much discussion with the war council, a decision is reached when the Blue Fairy presents them with the last enchanted tree in the land, which can be carved into a magic wardrobe and protect one person from the curse. They settle for sending Snow White, while she is still pregnant, into the wardrobe to another land and wait twenty-eight years for the prophecy of the savior to come true. ("Pilot")
As Geppetto and Pinocchio set out to carve the wardrobe, Prince Charming listens in as his wife questions the Blue Fairy for more details on the Dark Curse. The Blue Fairy tells her to have faith their plan will work, and if not, the curse will take them to a new land where their memories are erased and they will be slaves to the Queen's will. Snow White is also concerned exactly how the savior will know what to do. The Blue Fairy stresses in more vague terms that when the time comes, the savior will learn of their story. Just before leaving, the Blue Fairy requests to be trusted as she herself has the one thing they all need, which is hope. Snow White is crushed that she and Prince Charming can never be a family with their child and begins agonizing over their grim future due to the curse. He believes the unknown isn't always bad and life is full of twists and turns just like the curse. Prince Charming is sure that even though their chance to be a family is gone, it doesn't mean they can't have a different future together. To this, she affirms her decision to choose hope and believe things are going to work out for them. ("Going Home")
As time runs low while they await the Evil Queen's curse, Snow White can't come to the terms with the fact she will be away from her husband for twenty-eight years after going through the wardrobe. Prince Charming has faith they will eventually be reunited. They kiss, to which Snow White pulls away abruptly as she is having contractions. On the same day, the curse approaches. While Snow White is labor, Prince Charming attempts to move her to the wardrobe, but Doc advises against it. After birth, he and Snow White have a shared moment with Emma until realizing that their child must go through the wardrobe alone or all is lost. Prince Charming fights his way through many of the Queen's knights, while cradling Emma in one hand, to place her in the wardrobe. Once he does, Prince Charming sustains a grievously injury by the Queen's knights, but before passing out, sees them break open the wardrobe, which is now empty. Later, Snow White tries to bring him back with true love's kiss, which fails, and she has a confrontation with the Queen as the three of them are engulfed by the curse. ("Pilot")
After Regina takes magical preventive measures to undo Pan's casting of the Dark Curse, all the inhabitants of Storybrooke pay the price by returning to the Enchanted Forest and reverting to their prior personas. In a group, they manifest in the land of Princess Aurora and Prince Phillip where Regina mentions in passing that her old palace is still standing due to a preservation spell. Regina agrees to comply with Snow White's plan to travel there altogether as a strong front to ease the other inhabitants' minds. Prince Charming is informed by Grumpy, who was told by Jiminy, that fifty inhabitants landed in the Enchanted Forest two miles away. He tasks the seven dwarves with the job of spreading the word that everyone else should head for same destination as their group. Prince Charming is disappointed that Hook decides not to come with them and instead the pirate goes off looking for his ship. Baelfire wishes to stop off by his father's old castle, but Prince Charming persuades him that even if there is some way of reaching Emma and Henry, they wouldn't remember him. During the trek to the palace, Snow White searches for a missing Regina. The two women come back with three of the Merry Men, Friar Tuck, Little John, and Robin Hood, who accompany the group. As they near the palace, Regina discovers a protection spell, cast by whoever currently residing inside, is keeping them out. For the time being, Robin Hood suggests everyone can take shelter at Sherwood Forest. ("New York City Serenade")
As the group depart for Sherwood Forest, Regina proposes to Prince Charming and Snow White that she sneak into the palace through underground tunnels and deactivating the shield to allow entry. Suddenly, a flying monkey attacks, though the creature is quickly disarmed when Regina turns it into a stuffed animal. In a group discussion, Belle shares knowledge about the flying monkey's origins in the land of Oz, so Regina determines the person in the palace is the Wicked Witch. The prince suspected that the witch's motives are personal and inquired the Evil Queen on her past with the Wicked Witch, to which Regina replied that she and the witch were never acquianted. A plan is set up to wait for Regina to bring the shield down and then mobilize the whole group into the palace. Once night falls, Grumpy gives the signal when he spots the dissipating barrier, meaning Regina was able to lower it, so Prince Charming orders for everyone to begin heading to their destination. ("Witch Hunt")
During a night's sleep in the palace, Prince Charming dreams of being in the old castle he and Snow White lived in. Hearing a baby's cries, he wanders into an undamaged nursery, where everything from the crib to the toys, appear exactly as how it once was prior to the curse. A grown Emma, dressed prettily in a blue gown, persuades him into a dance as practice for her first ball. Prince Charming is ecstatic, as this is the life he wanted for her, but she abruptly remarks that it is a shame it never happened since he failed her as a father. In an instant, the dream becomes a nightmare, with Emma being sucked into the wardrobe, as he is forced to let her go as she warns him not to "fail the next one". After waking up, Prince Charming receives news from Snow White that they are expecting another child, which shocks him, but he hides his true feelings from her. Unable to shake a foreboding fear, he attempts to calm himself by drinking. A sympathetic Robin Hood suggests that he seek out a plant called night root, which grows at the edge of Sherwood Forest, that can help overcome his fear. On arrival to the location, Prince Charming digs up night root, but climbs up a tower when he hears a woman's plea for help. Inside, a princess, Rapunzel, relates how she became trapped after being chased up the tower by a cloaked witch. She, like him, sought out the night root to conquer her fear, but it hasn't worked. He tries to free her, but the cloaked witch intervenes and is unmasked as a manifestation of Rapunzel herself due to the princess consuming the night root. As the witch uses the princess' lengthy hair as rope to climb up, Prince Charming encourages Rapunzel to fight back, to which she cuts off the tresses and destroys her false twin. They journey to the palace, where Rapunzel reunites with her parents, and Prince Charming admits his worries to Snow White, who reassures him they will face the unknown together. ("The Tower")
Just as Snow White intends to make a public announcement to the kingdom's citizens of her pregnancy, Belle returns to tell everyone about how Neal sacrificed his own life to resurrect Rumplestiltskin, who is now controlled by the Wicked Witch, Zelena. While everyone ponders what the witch wants from them, Aurora and Prince Phillip admit Zelena desires Snow White's unborn child and that they were forced to keep quiet or their own child would be harmed. After this revelation, Zelena arrives to turn the two into flying monkeys and then immobilizes Snow White. Prince Charming steps up to defend her, but he, too, is frozen in place. Zelena approaches to touch Snow White's belly; claiming the baby will be hers, and she departs soon after. Later, Prince Charming, Belle, Grumpy, Snow White, Regina and Robin Hood discuss counterattacking Zelena. They break into the Dark One's castle; gaining information from Rumplestiltskin about Glinda, the Good Witch of the South, who can help them. With his wife and Regina, they find a door leading to Glinda, but it can only be entered by the pure of heart. Prince Charming and Snow White pass into it to speak to Glinda about Zelena's weakness—light magic—a criteria Emma fits. Though the only way to reach Emma is with another Dark Curse, Regina refuses since it would mean taking Henry's heart. Prince Charming urges his wife to sacrifice his heart, which she inevitably accepts. As they say goodbye, Prince Charming remarks that their hearts have always been as one. Snow White crushes his heart; resulting in his death. Suddenly, Zelena swoops down to add a potion into the curse mixture, which will erase everyone's memories of their year in the Enchanted Forest. Before the curse spreads, Snow White, recalling her husband words, allows her heart to be torn out and divided; giving each half to herself and Prince Charming. From this leap of faith, Prince Charming is revived just as the curse closes in. ("A Curious Thing")
The name "James", which is a variant of Jacob, can mean "follower" or "supplanter". A supplanter is someone who takes the place of another person, place, or thing. This is fitting, as Prince Charming supplanted his twin James.
The name "David" is of Hebrew origin derived from the word "dwd" that means "beloved".
He is the first character to appear in the series. The opening scene of the pilot features him rushing to meet Snow White. ("Pilot")
Prince Charming was originally supposed to die in the first episode in the first season.
His flower crest is exactly the same as Emma's wrist tattoo.
Prince Charming's real name is David. He shares his name with another former shepherd, King David of the Bible. Ruth was the name of King David's great-grandmother, and also the name of Charming's mother. Prince Charming was betrothed to Princess Abigail. King David's third wife was also named Abigail.
Prince Charming appears in Henry's storybook in "Pilot", "The Thing You Love Most", "Snow Falls", "What Happened to Frederick", "Queen of Hearts", "Selfless, Brave and True", "Lacey", "The New Neverland", "Going Home", "Snow Drifts", "There's No Place Like Home", "The Snow Queen" and "Darkness on the Edge of Town".
Prince Charming's name appears on the list Tamara has in "The Evil Queen".
Henry's drawing of Prince Charming appears in "Fruit of the Poisonous Tree".