It started out as an ordinary day for Fluttershy – waking up in her house in Cloudsdale and going to work managing the weather for Ponyville alongside her best friend Cloud Kicker. However, she finds herself troubled by feelings she can't explain, feelings that something serious is wrong. When she starts having visions of a strange life with strange ponies, she's determined to find them and find out what's going on. But how can such a timid pony convince others of what she isn't sure of herself?

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.