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.