Luna tries to find the guts to ask out Shackles, one of her royal guards and the love of her life, but can't seem to. Celestia helps by being her wing pony and going out with his annoying friend, Thorn. When Luna asks him out he says no, leaving her heart broken. As her older sister lends a hoof to help get her confidence back up, Thorn annoys the crap out of her, making it even harder for her to help Luna. Will Luna ever get her date? And will Thorn get to go out with Celestia?