The episode is framed as Spike, Discord, the Cutie Mark Crusaders, Granny Smith, and Mrs. Cake explain to an unseen speaker that they were all trying their best to help with Big Mac and Sugar Belle's wedding.
From the perspective of flashbacks from Spike and Discord, Big Mac reveals his plan to them to propose to Sugar Belle by having a number of apples placed carefully around town, each with a riddle that would lead to the next, and eventually to a hill in Sweet Apple Acres, where he will build a bench like the shelves he build for Sugar Belle's shop and propose there. Spike, and reluctantly, Discord, offer to help; Spike will get a pie made by Mrs. Cake while Discord is responsible for planting the apples. In town, Discord finds Big Mac's little riddles rather sappy but goes and starts placing them. Sugar Belle, racing out from Sugarcube Corner, appears to miss the obvious apple Discord placed there, and finds that she keeps missing these as well.
Spike, meanwhile, finds that Mrs. Cake needs to bake twenty-one pies of various flavors and needs to place a small message in each, and can't get to Big Mac's request. Spike offers to help by using his fire breath to transfer the messages into the pies, but this ends up burning all the pies to a crisp. Meanwhile, a frustrated Discord transforms the apples into sentient beings and instructs them to deliver their messages correctly. However, his instructions are poor, and they start rampaging across the town. Discord teleports the apples all back to Sweet Apple Acres and goes to take Sugar Belle directly to the hilltop, but finds Big Mac no longer there. Teleporting Sugar Belle back to town, they run into Big Mac, Spike, and Mrs. Cake, while the Crusaders and Granny Smith are running away from a giant monster fused from the apples.
From Mrs. Cake and the Crusaders, Sugar Belle herself was planning to surprise Big Mac with her own proposal, by having Mrs. Cake bake the several pies so that each would have part of her proposal to Big Mac in them. Mrs. Cake agrees to do it but starts to get confused as to which flavor is which. As part of her plan, Sugar Belle has already had a special pie baked that she wants the Crusaders to deliver to Big Mac, as like the one he tried to bake her on Hearts and Hooves day, this pie has a message to bring Big Mac to Sugarcube Corner. The Crusaders go to Sweet Apple Acres, but can't find Big Mac, only that they are missing him by moments, though find his plans to make a bench and figure he is looking for help. The Crusaders try to check around town to find him, but have no luck. Eventually they return to the farm and ask a sleeping Granny about Big Mac, at which time the enchanted apples are teleported into the farm by Discord, and morph into a giant apple creature, intent on delivering their message to Sugar Belle. The Crusaders and Granny run from the creature back into town, running into the others.
Discord eventually disenchants the apples as the others all start to blame each other for ruining Big Mac and Sugar Belle's day. Big Mac, disappointed, goes back to Sweet Apple Acres, with Sugar Belle following him. He tells her he wanted to make this a special day, and he feels he keeps messing things up when it comes to their relationship. However, Sugar Belle encourages him to remember that his parents had a much harder time in getting to their marriage, and shows him Bright Mac and Pear Butter's rock and the intertwined apple-and-pear trees around it that they planted, a sign that their relations stood over that test of time. Sugar Belle is not upset that things didn't work out since their relationship is still strong, helping to raise Big Mac's spirits. In the shadow of the intertwined trees, both Big Mac and Sugar Belle propose to each other. Discord teleports the others to the spot with a celebratory meal as a way to make up for their failures earlier in the day.
Spike, Discord, the Crusaders, Mrs. Cake and Granny Smith finish up their stories to Applejack, minutes before the wedding ceremony, taking place on the same spot as Bright Mac and Pear Butter's ceremony.
- Actor Allusion: As Granny Smith describes her Star Trek-like dream, she mentions Grand Pear and Discord being there. Their voice actors (William Shatner and John de Lancie, respectively) played roles in said franchise.
- An Aesop: You don't need to make a Grand Romantic Gesture to prove your love for another. Sometimes, the simpler ways are best.
- Attack of the 50-Foot Whatever: As Discord's apple monsters fuse together into one, they eventually become a huge apple creature, stalking through Ponyville to find Sugar Belle.
- Bad Vibrations: Just before the giant apple monster appears, Granny Smith and the CMC see a bucket of water shaking.
- The Big Damn Kiss: After Big Mac and Sugar Belle propose to each other and Big Mac ties Sugar Belle's ring around her neck, the two share a kiss on the lips together. This marks the first true kiss the two have shared on-screen together and one of the only ones seen throughout the series, instead of simply nuzzling or kissing on the forehead.
- Book Ends: A generation ago, Bright Mac and Pear Butter had a simple wedding in the orchard and planted seeds. Now their son Big Mac marries Sugar Belle under the very trees they planted, coming full circle.
- Botanical Abomination: The final result of the living apples fusing with one another is a towering, monstrous amalgam of fruity flesh, bulging with dangling arms and half-formed apple monsters fused into its body and mindlessly reciting Big Mac's attempted marriage proposal as it tramples its way through town.
- Bowel-Breaking Bricks: Almost a Freeze-Frame Bonus, but when Discord suddenly teleports on the marketplace, a hen that was standing atop a goat hatches an egg in surprise.
- Breather Episode: This is the last regular "filler" episode before the big three-part Grand Finale which comes up next.
- The proposal and wedding of Big Mac and Sugar Belle takes place beneath the apple-pear trees of Pear Butter and Bright Mac.
- The events of "Hard to Say Anything" and "The Break-Up Breakdown" are brought up; the CMC wanting to make up for their mistakes in the former (and the new shelf Big Mac made for Sugar Belle being mentioned as well).
- The Cameo:
- Fluttershy and her animal sanctuary are briefly seen during the Crusaders' search for Big Mac.
- Among those attending the wedding include Double Diamond, Party Favor, and Night Glider from Sugar Belle's former village, and Burnt Oak and Grand Pear who had been there for Big Mac's parents' marriage, as well as Granny Smith's Gold Horseshoe Gals.
- Cannot Keep a Secret: Despite his claims to the contrary, Discord reveals several secrets about certain ponies, such as how Fluttershy is afraid of clowns, or how he once found Twilight sleeptrotting through Ponyville.
- Character Development: For most of "The Break-Up Breakdown", Discord had a very low opinion regarding romance, showing barely any interest in Big Mac's romantic woes. Here, he is absolutely ecstatic to learn that Big Mac is planning to propose to Sugar Belle.
- Confession Cam: It seems like Spike, Discord, and the Cutie Mark Crusaders are doing this at first to explain everything that happened in the episode up until the wedding, but it turns out that they're actually explaining the situation to Applejack.
- Continuity Nod:
- Didn't Think This Through:
- Discord's Exact Words — it doesn't occur to him to actually tell his living apples who they're supposed to deliver their messages to, resulting in them running loose through town and shouting their messages at everyone they met.
- Spike attempts to help Mrs. Cake place a bunch of messages into sweets with his fire ability. Unfortunately, the fire from the messages popping into the desserts burns them all to a crisp.
- Dramatic Irony: The audience knows that Big Mac and Sugar Belle are trying to propose to each other at the same time, but the characters don't. It all comes to a head in the third act.
- Exact Words: Discord brings the apples to life with his magic and tells them to go to their designated destinations on their stems and deliver their messages. However, this leads to the apples running wild and telling everypony they see their messages. Discord realizes his goof quickly.
- Expy: Discord being one of Q is lampshaded as a part of Granny Smith's Star Trek Shout-Out dream.Granny Smith: And then Discord showed up and, well, y'know, he was pretty much the same.
- Face Palm: Big Mac facehoofs after the giant apple monster show up and Discord says that at least, the message was delivered to Sugar Belle.
- Fairytale Wedding Dress: Sugar wears one at her wedding with Big Mac.
- Fourth Wall Psych: Throughout the episode, Spike, Discord, Mrs. Cake, and the CMC appear to talk to the viewer about how the Wacky Marriage Proposals went wrong. Turns out they were all talking to Applejack the entire time.
- Fusion Dance: The living apples Discord creates merge together by touch, eventually becoming one giant apple monster.
- Got Volunteered: Spike recruits Discord to place the riddle apples across Ponyville (to Discord's annoyance).
- Hand Gag: Discord covers up Spike's mouth with his eagle talon to keep him from guessing the next step of Big Mac's proposal (with the talon detaching from his arm to keep Spike quiet).
- Happily Married: Big Mac and Sugar Belle get married by episode's end.
- How We Got Here: The first two acts of the episode are mostly in a flashback format, narrated by Spike, Discord, Mrs. Cake and the Cutie Mark Crusaders.
- Immediate Self-Contradiction: Big Mac didn't want to tell Discord about his upcoming proposal to Sugar Belle because he can't trust Discord to keep it a secret. Discord claims he's great at keeping secrets, then rattles off a few secrets he's been told before. After realizing what he's just done, Discord concedes the point.
- Implausible Deniability: Discord is quick to deny having anything to do with the giant apple monster. He only gives in after it rattles off Big Mac's proposal speech.
- Irony: Despite his own habit of Complexity Addiction, Discord is quick to suggest that Big Mac's proposal to Sugar Belle could be done more simply, via simply handing her the riddle apples.
- Jerkass Ball: Spike insults Mrs. Cake's baking twice.
- Jerkass Has a Point: While he wasn't exactly blameless himself, Discord had a point in calling out Spike for ruining Mrs. Cake's bakery. Spike concedes the point.
- Lampshade Hanging: As Big Mac points out, every one of his previous attempts at a Grand Romantic Gesture have ended in disaster.
- Lower-Deck Episode: None of the main characters appear except for Applejack and Fluttershy briefly, and they don't get speaking lines. This episode revolves purely around the secondary cast for one last outing before the finale.
- Meaningful Background Event: In a "blink-and-you'll-miss-it" moment, Lyra Heartstrings proposes to Bon Bon/Sweetie Drops◊ during the apple rampage. The favor is returned.
- Missed Him by That Much: When the Crusaders are searching for Big Mac they check the Apple Acres barn first and don't see him, before Apple Bloom suggests they try finding him somewhere else instead of waiting. Shortly after they leave, Big Mac arrives, looking for a screwdriver to finish building his table for Sugar Belle.
- Must Make Amends: The Cutie Mark Crusaders are intent on helping Sugar Belle with her proposal, as a way to make up for the mess they made during their attempts to get her and Big Mac together in the first place.
- Never My Fault: When the giant apple monster appears, Big Mac immediately yells "Discord!" Discord protests with "Why is it everypony automatically assumes I had anything to do with this?" He's forced to yield when the apple monster makes Big Mac's marriage proposal for him.
- Nothing Is the Same Anymore: Big Mac and Sugar Belle get married.
- Not Me This Time: When Big Mac and Sugar Belle suddenly vanish mid-conversation, Discord insists that he wasn't the reason for it.Discord: Okay, this time, it really wasn't me!
- O.O.C. Is Serious Business: Mrs. Cake, who is usually a good cook with sweets, rushes so much to get all the desserts ready for Sugar Belle's plan to propose to Big Mac that her desserts end up tasting very bad.
- Overly Narrow Superlative: Spike claims to be the most romantic dragon he knows. Considering that dragons have hardly been depicted as sensitive or romantic, and that the number of dragons Spike knows personally is in the single digits, this isn't saying much.
- Poor Communication Kills: A lot of the conflict in this episode comes from people not talking to each other. Spike and Mrs. Cake don't communicate because they're trying to keep a secret, Big Mac and Sugar Belle are each trying to pull off a Wacky Marriage Proposal, and Discord makes things worse by taking a fast and easy way out of his responsibilities.
- Queer Establishing Moment: Lyra and Bon Bon are seen proposing to each other in the background, revealing that they're lesbians.
- Relationship Upgrade: Lyra Heartstrings and Bon Bon become an Official Couple with their simultaneous proposal.
- Rocky Roll Call: When the two groups converge:Big Mac: Sugar Belle!
Sugar Belle: Big Mac?
Big Mac: Discord!
Discord: Mrs. Cake!
Mrs. Cake: What did I do?
Discord: Nothing. I thought we were just saying each other's names.
- Sesquipedalian Loquaciousness: In recalling what he did in the past, Discord says he "precipitated liquid cocoa on Equestria and herded long-limbed Leporidae", or making it rain chocolate milk and making long-legged rabbits from "The Return of Harmony".
- Ship Tease: Discord claims that Octavia and Bulk Biceps went on a date together once, but the exact details are unknown.
- In the cold open, Discord reminds Big Mac and Spike that they are pals, friends, and amigos, briefly flashing them into outfits based on ¡Three Amigos!. (This also can double as an Actor Allusion for Discord based on the TNG episode "Deja Q".
- Granny Smith describes going into space with Grand Pear in her dream; specifically, where nopony has gone before. She goes on to describe how Mudbriar was there and as logical as ever, but with pointed ears, and Discord was pretty much the same.
- The Framing Device described in Fourth Wall Psych recalls The Office (US).
- Speak in Unison: Big Mac and Sugar Belle propose to each other at the same time.
- Stealing the Credit: Discord is quick to take the credit for everyone arranging a "do-over" for the proposal.
- Stealth Pun: Discord animates a bunch of apples to deliver the messages to Sugar Belle, in affect, turning them into apples of discord.
- Strolling Through the Chaos: While everypony else is running in terror from Discord's apple monsters, Lyra and Bon Bon are proposing to each other, not seeming to notice what's going on.
- Suddenly Shouting: Twice: both Discord and later Apple Bloom shout out to their friends that Big Mac and Sugar Belle are going to propose, with the yelling so loud as to reverberate into Ponyville and annoy more than a few ponies there.
- Tears of Joy: Applejack gets teary-eyed after Discord, Spike, Mrs. Cake, and the Cutie Mark Crusaders finish their story to her, probably because she's so happy that her brother is finally getting married.
- Tempting Fate: After Big Mac's proposal crashes and burns, Spike says that "at least it can't get any worse". Discord responds with "As the Lord of Chaos, I'd advise against saying things like that." Sure enough, immediately afterwards, a giant apple monster roams into Ponyville.
- They Do: Sugar Belle and Big Macintosh end this episode with their wedding, even doing so in the shade of the apple-pear trees planted by Pear Butter and Bright Mac.
- Trailers Always Spoil: The official summary of the episode states that both Big Mac and Sugar Belle are planning to propose, something that isn't revealed until later in the episode.
- Unfazed Everyman: Lyra and Bon Bon don't seem very worried about the apple monster rampage going on, and instead use the opportunity to propose to each other.
- Unreliable Expositor: During the Cold Open, Spike claims that Discord "insisted" on being involved in the proposal. But in the actual course of events, Spike invokes Got Volunteered on an annoyed Discord.
- Wacky Marriage Proposal:
- Both Sugar Belle and Big Mac try to do this to one another. Big Mac tries to get Sugar Belle to see apples with notes, and Sugar Belle tries to get various desserts made with her proposal in them. However, things get increasingly out of control as Discord's powers and miscommunication keep occurring.
- Lyra and Bon Bon avert this. It's in a Meaningful Background Event, but it's a simple "kneel down and present the ring" kind of proposal. Admittedly, it's while apple creatures are scaring everypony else half to death, but even so...
- Wedding Episode: Big Mac and Sugar Belle get married at the episode's end.