Rarity is alone on Hearts and Hooves Day, and she's not happy about it. A friendly afternoon in the park with Applejack promises to turn their friendship to something more – or at least it would, if either of them would simply talk to the other about it.

Between her awkward sort-of romance with Applejack, her desire to help Fluttershy find a special somepony of her very own, family, friends, and the general day-to-day chaos that is life in Ponyville, this fashionista's got her hooves full.

Side story to The Life and Times of a Winning Pony and the rest of the Winningverse. My thanks to Chengar Qordath and Comma-Kazie for their support and pre-reading assistance.

Twilight and Spike return to the Castle of the Two Sisters, only to find that their previous foray into its depths may not be what they remember.