Rarity and Sassy Saddles are preparing the Canterlot Boutique for the transition from winter to spring (or, as Rarity calls it, "springsition"). While Sassy is a bit frantic, Rarity assures her that everything is under control — she's been working on all of the projects associated with the change. As she cleans, though, she discovers a picture of herself and Sweetie Belle playing together, and realizes that she's been so busy with her three shops that she hasn't spent any quality time with her sister in ages. Sassy soothes her boss's dramatic sobbing by offering to watch the shop while Rarity goes to Ponyville for a visit. Rarity eagerly agrees, and plans to make their day amazing.
Meanwhile, the Cutie Mark Crusaders are busy with their full-time work of helping a confused Pegasus — this time a colt named Chipcutter — find his destiny (it turns out he's a sculptor, given his tendency to make statuary out of his lunch). Back at the clubhose, the three celebrate another successful job and prepare to help Zipporwhill, who has recently lost the attention of her pet puppy, Ripley. Just as Zipporwhill arrives, Rarity busts in, and tells Sweetie Belle she has planned a day of activities for them; as she does, she unknowingly insults her younger sister by insinuating that her work as a Crusader is "cute." Apple Bloom and Scootaloo assure Sweetie Belle they can cover for her, and the two sisters set off.
Rarity and Sweetie Belle set out on a trip through Ponyville, with Rarity taking her sister to do all of her "favorite things." Unfortunately, Rarity seems unable to realize that Sweetie Belle isn't a baby any more, as all of the activities are decidedly childish: a puppet show (Sweetie Belle's more interested in experimental blackbox theatre now), eating (literally) bite-sized sundaes, and waiting in a long line for a balloon animal. Meanwhile, Apple Bloom and Scootaloo discover that Ripley is no longer having any fun playing with Zipporwhill, despite all of her efforts to play with his old toys and praising him as her "puppy." Sweetie Belle gets a chance to check in and notes that Ripley is awfully big for a puppy before Rarity whisks her off. Zipporwhill becomes dejected that she can no longer live up to her cutie mark.
Eventually, while they are taking pictures in funny costumes, Sweetie Belle tells Rarity that she's grown up now, and that she no longer likes doing such juvenile activities; the fight causes the younger pony to run off. Thinking she's being ungrateful, Rarity follows her as Sweetie encounters Zipporwhill by herself. Zipporwhill tells Sweetie Belle that Ripley doesn't even show interest in his favorite toy, a small chew bone, and Sweetie Belle realizes what the problem is. She brings Zipporwhill back to the others and explains that Ripley's a full-grown dog now, not a puppy; as such, he wants to play games appropriate for a dog his age. Rarity, who's been waiting to confront Sweetie Belle, overhears this and realizes that she needs to treat her sister the same way, instead of keeping her stuck in the past. The girls make up while Zipporwhill finds Ripley very interested in playing fetch-the-stick, restoring the bond between the two.
Rarity and Sweetie finish off the day with a new activity: enjoying giant, oversized sundaes that they can't possibly finish. The mare who runs the ice cream parlor takes a picture of the two, which ends up on Rarity's desk as a sign of the sisters' newly mature relationship.
- An Aesop: Time changes everything and everyone. The only way to keep from being left behind is to accept it, and change with them.
- Aesop Amnesia: Sweetie Belle mentions to Rarity that her tastes have changed (Experimental Theatre and Salads instead of Puppet Shows and Tiny Ice Cream Sundaes) but when Rarity reacts with surprise to those revelations, Sweetie Belle backpedals to avoid hurting Rarity's feelings. Apparently, Sweetie Belle still hasn't found her backbone since The Applewood Derby. It could be justified when you consider that Sweetie Belle knows that Rarity isn't acting in her own self-interest this time but is genuinely trying to make her little sister happy, making it harder to call her out without seeming ungrateful.
- Affectionate Gesture to the Head: Rarity tousles Sweetie Belle's mane after hearing her refer to Zipporwhill as the Crusaders' "client". Although Sweetie Belle takes it in stride, it comes off as condescending, as Rarity clearly thinks the CMC are playing pretend instead of legitimately providing a service.
- Age-Stereotypical Food: Rarity takes her little sister Sweetie Belle (who's around preteen aged) to an ice cream parlour that they haven't visited in years. Rarity gives Sweetie Belle the ice cream sundae she used to always have, but Sweetie Belle finds it childish. Perhaps justified because the sundae was very physically small, so it wasn't big enough to satisfy a larger filly.
- Amplified Animal Aptitude: Ripley rejects his puppyhood things because he knows he's an adult dog. In reality, most dogs never outgrow squeak toys, balls, and the joy of being told they're a good puppy.
- Banana Peel: Part of the puppet show Rarity and Sweetie Belle attend has a gag involving the puppets sliding around on a banana peel.
- Break the Cutie: This happens to Zipporwhill when Ripley ignores all her affectionate attempts to get him to play with her, making her think her beloved dog doesn't love her anymore and causing her to doubt her talent with animals. She ultimately starts crying over it.
- The Bus Came Back: Sassy Saddles and Zipporwhill (along with her now adult dog Ripley) reappear.
- Character Development: The whole point of the episode. Sweetie Belle isn't the same little filly she was back in Season One: her habits, telekinesis, and sense of responsibility have greatly improved with age. Unfortunately, the Genre Blind Rarity can't realize that.
- Characterization Marches On: Zipporwhill is much more down-to-earth, nowhere near the fast-talking hyperactive loon she was in her debut as a bit character. If anything, her movements and speech are actually slow. It could be related to her gloomy mood for most of the episode or, given the episode's theme, that she's simply matured.
- Continuity Cavalcade: The Crusaders' wall of photographs includes Cheerilee and Big Mac, Babs Seed, Pipsqueak, Diamond Tiara, Bulk Biceps, Tender Taps, Rarity, Applejack, and Rainbow Dash and Gabby the Griffon.
- Comically Missing the Point: Sassy Saddles, who's been out of the room while Rarity is reminsicing about her past with Sweetie Belle, reenters with the news that they're out of vermilion satin, just before Rarity breaks down completely. Sassy takes this as Rarity's reaction to the low supply of fabric:Sassy Saddles: I... I can order more!
- Continuity Nod:
- One of the outfits Rarity dons when she and Sweetie Belle are getting their photos taken is Pinkie Pie's chicken costume.
- The butterfly wings that Rarity received for the Best Young Flyers Competition also reappear during the photoshoot.
- Claude the puppeteer returns to put on a show for foals in the park.
- Rarity mentions running three shops while helping #2 through a display transition. Perhaps she's going to Manehatten later.
- Dogged Nice Guy: Twisty Pop (the balloon artist) when he gives Rarity a heart-shaped balloon.
- Double Aesop: Sweetie Belle teaching Zipporwhill to accept that that her dog has grown up and moved on from his old interests causes Rarity to realize her sister has also changed, and that she should stop treating her like a foal.
- Dramatically Missing the Point: After being called out by Sweetie Belle for doing the activities she used to like (but not anymore), Rarity thinks she's being ungrateful. After all, she did take the time to plan out a whole day together with Sweetie Belle. It isn't until she sees Sweetie Belle helping Zipporwhill with the same problem that it finally clicks in Rarity's mind.
- Fainting: Rarity's tendency to faint at dramatic or emotional moments is brought up when she mentions she's so excited at the prospect of spending the day with Sweetie Belle that she could faint, and then asks if the CMC have a fainting couch anywhere.
- Growing Up Sucks: Done in an extremely original way — it's subverted with Sweetie Belle, who's enjoyed growing up and the newfound responsibility her duty as a Cutie Mark Crusader has brought her, and, to a lesser extent, Ripley. But from Rarity and Zipporwhill's perspective, it's played straight: they would prefer that their sister and pet, respectively, remain youthful forever.
- Rarity praises the CMC for having come a long way, not even realizing that this also means that they're not the young fillies as she remembers them anymore.
- Back in "Sisterhooves Social", Rarity tries to make it up to Sweetie Belle by offering to do fancy and mature activities with her which Sweetie Belle doesn't want. Now Rarity is doing young and cute activities with Sweetie Belle that she used to like but doesn't anymore.
- Not Allowed to Grow Up: Averted all around. Zipporwhill is taller than she was in her first appearance, and Ripley has gone from being a puppy to a full-grown dog. Sweetie Belle has also grown more mature than she once was, to the point where the activities she and Rarity used to indulge in no longer appeal to her.
- Nothing Is the Same Anymore: Both as a trope and invoked by the episode. Zipporwhill has grown since her last appearance (as well as her pet dog Ripley), while Rarity realizes that Sweetie Belle is no longer the same filly she was years ago.
- Ocular Gushers: Rarity gets these when she realizes how much she misses spending time with Sweetie Belle.
- Precious Puppy: Zipporwhill treats her dog Ripley like this, even though he has since become an adult dog and isn't interested in his puppy activities anymore, causing Zipporwhill to lose touch with her pet.
- Plot Parallel:
- The plot of Rarity dragging Sweetie Belle through a day full of activities she's too old for is is mirrored by the subplot of Zipporwhill trying to figure out why her puppy isn't playing with her anymore, not realizing her dog isn't a puppy anymore.
- Sassy Saddles's assuring Rarity that she can manage the shop on her own matches (to the point of using nearly the same dialogue) Apple Bloom and Scootaloo's promising Sweetie Belle that they can manage Zipporwhill's problem on their own.
- Reality Ensues: Being responsible for the operation of several fashion stores, particularly if they are far from home, doesn't really leave much room for quality time with your sister.
- Stealth Pun: During the photo shoot, Rarity dresses up like a butterfly, and Sweetie Belle a caterpillar — in other words, the imago and larval stage of a caterpillar's life cycle, which reflects Rarity's belief that her sister is still a baby. Same thing when they dress respectively as a chicken and an egg, a flower and a seed, etc.
- Tears of Joy: Rarity is seen getting misty-eyed as she tells Sweetie Belle that she realized she's not a little filly anymore, and that she misses doing all of the things they used to do together.
- Tuckerization: Zipporwhill's puppy, Ripley, is named for "Big" Jim Miller's dog.
- Violation of Common Sense: The Crusaders' method of moving a giant stone block down a mountain? Using it like a sled!
- Your Makeup Is Running: As usual, whenever Rarity cries, she has this paired with Ocular Gushers.