Sora is staring at Kairi's lucky charm while Donald and Goofy sleep around a bonfire. He is interrupted by Jiminy Cricket, who is updating his "Jiminy Memo", a record about their adventure. Sora wonders out loud how different his life would be if he, Riku, and Kairi had gone on the raft, and worries if he would ever see them again. Jiminy cheers him up by stating that he is destined to return to Destiny Islands with his friends just as Donald and Goofy are destined to return the King to Disney Castle. Sora awakens after falling asleep to see a man in a black coat telling him "ahead lies something you need, but to claim it, you must lose something dear." Before Sora could question him, he is interrupted by Goofy, who is ordering fast food in his sleep.
The group eventually find themselves in front of a huge castle known as Castle Oblivion and agree to enter in the hopes of finding Riku and the King. However, once inside, Sora gets the feeling that he dropped something and the man in the black coat appears to tell him that the dropped item was his memory. Donald shouts at Sora for falling into his trap and accuses him of being a Heartless. The duck then tries to attack him, but learns he has forgotten all of his spells. The man tells the three that they started losing their memory the minute they stepped into the castle prompting Goofy to reassure himself he hasn't forgotten the alphabet. The man tells them that they'll find people they know and people they miss before passing through Sora, causing memories of his previous journey to appear rapidly. He informs Sora that he sampled his memories and turned into cards, before giving one to the Keyblade wielder. He instructs him to hold the card to a door at the end of the hall and beyond it, another world would appear before vanishing. Jiminy frantically tells Sora that he doesn't trust the man and starts pondering his cryptic words, but Sora reassures him that he felt they will find something in the castle, a feeling Donald, Goofy, and Jiminy also got.
Sora opens the door and the friends start to walk through as the man reappears behind them stating the more they advance, the more they'll figure out the meaning of his cryptic words: "to find is to lose and to lose is to find." As Sora passes through the door, he is shocked to see a familiar world.