Five years ago, The Cutie Mark Crusaders helped Diamond Tiara find her purpose in life. Ever since then she's known that she was meant to be a leader. Now, she's trying to find out how she can help ponies with her talent and passion.

After much searching, she finds The Hollow Shades, a deserted city just Northeast of Foal Mountain. She plans to use her extensive funds to make the city a home to ponies that have no other.

Will her friendships with two of the most legendary villains in Equestrian history destroy her attempts at trying to tame the Hollow Shades? And even if they don't, would her parents take her allowance away if they found out that her heart was already taken by a stallion of whom they would never approve?