Sweetie Belle and Scootaloo hang out in a gin joint where Sweetie sings jazz. She has a good thing going for her. Until she overhears a conversation that makes her question everything.
Scootaloo and her friends are now in High School and have started to grow up more. Scootaloo has a coltfriend, and everything is fine, until one day she feels sick, and things go from there.
A first kiss is supposed to be magical. In this case, it is, but Scootaloo has no idea why. Turns out nopony has had that talk with her yet, and she certainly hasn't figured it out for herself.
Scootaloo is alone. She's failed her family, her friends, her destiny - everything. Running away from her problems, Scootaloo lost herself in the sprawling city of Las Pegasus. Now, her life is meaningless... until a letter arrives from Ponyvill
Sweetie Belle is falling, and there's nopony around that can save her. Can she find a ray of light in her life as she reflects on her one largest regret?