Season 1, Episode 6:
Dr. Whale: No.
Mary Margaret Blanchard: How do you do that?
Dr. Whale: By never doing what's expected. It keeps life interesting.
Emma learns about Sheriff Graham's affair with Regina and David is forced to choose between staying with Kathryn and leaving her to start a relationship with Mary Margaret. In the fairy tale land that was, the back story of Prince Charming is revealed along with a life-changing event that forever altered his destiny and a secret deal made between his "father", King George, and Rumplestiltskin.
- Actually Pretty Funny: When James (the original, not David impersonating him) asks Midas's forgiveness for not shaking his gold-cursed hand, the king stares at him emotionlessly—then bursts out laughing.
- Ambiguous Situation: Just as he's leaving the pawn shop, David discovers the old windmill from his and Kathryn's yard...and as he watches its blades spin, says it was his and he remembers. Gold, watching very intently, asks him if he's sure. Next thing we know, he's deciding to stay with Kathryn. It's unclear what exactly happened, but between Gold's small smile and Regina having sent David there in the first place, it wouldn't be surprising if there was some kind of spell on the windmill (placed there by her) to make him "remember" enough memories to want to go back to Kathryn and try again, and Gold (now aware of who he is) could sense this and was testing David, perhaps to try and undercut Regina.
- Bait-and-Switch: David is stopped from studying the mobile (which he and Snow White had had over baby Emma's crib) by Gold interrupting with, "Charming", his Enchanted Forest nickname. Then, when David asks what he means, he explains he was talking about the mobile.
- In "The Price of Gold" Rumpelstiltskin was tricked into signing a deal that traded twin babies for monetary gain. Here in this episode we find out he actually made such a deal with Charming's mother.
- We also find out why in that same episode he was able to simply appear and take the Fairy Godmother's wand—because she was associated with King George's family in some way, and the king gave Rumple permission to do so in return for replacing the slain Prince James with his twin.
- Caught With His Pants Down: Graham is caught sneaking out of Regina's house by Emma, while half-dressed.
- Changeling Fantasy: Inverted. Prince James was actually born a farmer's son and sold to the king to pass off as an heir. The same happens to his twin brother David.
- Characterisation Marches On: One of the soldiers says of Prince James "he was the bravest man I ever knew". The episode "Tiny" shows that James was an amoral womanising scoundrel. Either this or a Retcon, although it's also possible the soldier was lying, didn't know James' true nature, or had a very different view of what bravery was.
- Chekhov's Skill: Prince Charming's skill in shepherding animals comes in handy when he lures the dragon into a trap.
- Composite Character: Due to both his background and the Twin Switch Rumple arranges to replace the suddenly-deceased James, Charming turns out to also be The Prince and the Pauper—except it's done to save his mother's farm and the kingdom rather than to see how the other half lives (that ends up being enforced by George).
- Cryptic Background Reference: When Midas demonstrates his curse as a show of good faith for King George, he gives a warning to his soldier who is not being careful enough with his gauntlet: "Remember what happened to Frederick." This isn't explained until much later, in the episode of the same name.
- Decapitation Presentation: The dragon's gilded head is presented to Midas.
- Donut Mess with a Cop: Invoked when Sheriff Graham offers Emma (who has just become his deputy) a box of donuts to persuade her to work a late shift. As he presents them, he quips that some cliches are true.
- Drowning My Sorrows: Mary Margaret in Granny's after David tells her he's staying with Kathryn.
- Even Evil Has Standards: Rumple says that magic cannot bring back the dead. In Wonderland, Cora lists this as one of the main rules - you can't make someone love you, can't change the past, can't bring back the dead - but Zelena breaks the Time Travel "law", implying that bringing someone back from the dead can be done, which is then confirmed by the absolute disaster that Frankenstein's attempt creates. Thus, Rumplestiltskin is smart enough to know that meddling with dead people is not a good idea.
- Five-Second Foreshadowing: At the end of his fight with the Behemoth, James sits up from being seemingly slain on the ground, impales the Behemoth, and smugly tells him "make sure I'm actually dead next time." A few minutes later, when James is giving a Rousing Speech to his men in preparation for facing the dragon, the not-dead Behemoth sits up and impales him.
- Hidden Backup Prince: Prince James has a twin brother, raised as a shepherd.
- Identical Twin ID Tag: The only way to tell James from David was the hair - James had his short while David's was longer - and the clothes - James of course was royalty while David was a farmer.
- Irony: George tells David after the betrothal is set and he's about to go to Midas's palace with Abigail that he's on the road to true love—not knowing that this is literally true, since Ruth had said her ring would lead him to true love as it did her and the road they take through the forest is the one where bandit Snow robs him of the ring.
- Manipulative Bitch: After she finds out David has left Kathryn and plans to be with Mary Margaret, Regina deliberately gives him wrong directions to the toll bridge—which not only keeps him from getting there in time to meet her but takes him past Gold's pawn shop, where she knows the windmill he and Kathryn once had in their yard can be found.
- Marry for Love: David wants this, despite Ruth urging him to find the money from an Arranged Marriage to save their farm. By irony, when he is given An Offer You Can't Refuse from King George, Ruth urges him to stick to his principles but thanks to the threat to the kingdom (and to him and her), David goes along with it. Meanwhile in Storybrooke the amnesiac David also wants to be with someone he loves (and his missing memories mean he doesn't love Kathryn), which is why he chooses to go to Mary Margaret...until he gets his memories back, and then feels he must honor the love he once had for Kathryn.
- Match Cut: Indirect, but the scene where Charming looks at the golden sword he just used to slay the dragon cuts to a scene of him in Mary Margaret's schoolroom, where she's cutting into an envelope with a golden letter opener.
- Meal Ticket: King George wants his son to marry Midas's daughter in the hopes that Midas will use his power to restore his kingdom's wealth. Things work out pretty good until George's son dies, forcing him to get help from an evil sorcerer to get someone identical to take his place.
- Meaningful Echo: "You can't have everything" and "Didn't see that coming, did you?"
- Meaningful Name: David, who is revealed in this episode to have been a shepherd in the Enchanted Forest before taking his twin brother's place as the prince.*
- An Offer You Can't Refuse: With his kingdom on the line, this was King George's method of forcing David to play the part of James for the rest of his days. He threatened to destroy David's mother and anything else David held dear if he did not comply.
- Playing Possum: The "Brute" at the beginning pretends to be dead for several minutes before stabbing James in the back.
- Plot-Triggering Death: Prince James killed in a duel.
- Sex for Solace: After David changes his mind because of his returned memories and goes back to Kathryn, Mary Margaret is comforted at Granny's diner by Dr. Whale, and ends up having a one-night stand with him.
- Small Role, Big Impact: The Behemoth only appears on screen for a few minutes in one episode and nothing of importance is revealed about him; however if he hadn't killed Prince James then Charming would never have taken his dead brother's place and a large majority of the plot would never have happened.
- Shown Their Work: In a rather obscure reference, Midas tells his men to put the dragon's golden trophy head between "the chimaera and the mapinguari", the latter being a legendary Bigfoot-like beast from the Amazon.
- Standard Hero Reward: Played for Drama and nastily Deconstructed. The shepherd boy brought in as a last-minute swap for the deceased prince slays the dragon and saves his widowed mom's farm. Unfortunately, the kingdom is flat broke, meaning he's being forced to marry some Royal Brat in order to secure a fat dowry for the land's empty coffers. Otherwise, the king is going to destroy his mother and is willing to murder him to see it through.
- There Is Another: Rumplestiltskin says this verbatim when saying to King George that James had a twin brother who could replace him.
- True Blue Femininity: Princess Abigail has her pale blue dress.