A noble earth-pony family, fallen somewhat on hard times, is killed in a mining accident. They leave behind a single male heir, who is in sore need of a guardian, and of protection. Celestia takes the young pony under her wing and delivers him not to ponies - not earth, unicorn or pegasus - but to a dragon, an ambassador, an old friend of hers.

Playing a game which may just be deadly to the uninformed, the dragon decides that the one path open to him to ensure the safety of his charge and to carry out his sworn duty, is to adopt.

Twilight Sparkle is the smartest student in Princess Celestia's school, but her awkwardness and poor social skills have ruined her chances of having any sort of dating life. Can she overcome her problems and find the perfect stallion? Will her older brother Shining Armor help or hurt her chances for love, as she goes on her first date ever?

This story takes place in Canterlot, about six months before the first episode of Friendship is Magic.