Braeburn's visit to see his relatives in Ponyville doesn't go quite as he expected. After discovering that he doesn't have a Special Somepony, Applejack resolves to fix this problem - by having Braeburn try to date each of her friends, in hopes things will click between one of them and her cousin.

Unfortunately, the road to Tartarus is paved with good intentions, and the poor stallion finds himself being roped into one disaster after another. Bear attacks, wearing a fancy suit, and a near death experience are just a few of the challenges he soon finds himself facing. Will Braeburn succeed in finding a Special Somepony to call his own? Or will Applejack's attempts to help her cousin only make things worse for him? The answer may surprise everypony.