Jack wasn't exactly sure what it was that he was getting into, only that he had a lovely bottle of rum tucked into his pocket and he planned on making the Miss Delphine at least try a lick, considering her avoidance on the subject as it were. He'd kindly left a note for Rinoa explaining he had gone out for tea...or coffee...or something with a new friend (and yes, it read that way on the slip of paper), and that he would return shortly after.
While he had come into the ownership of more "normal" clothes, he still felt that first introductions should be done in his full pirate regalia, as that was who he was. It was every bit a part of his as his hat, as his ship, as hit rum. And the various treasure, trinket, and trophies that adorned his person upon his belt and within his hair were stories withing themselves.
Jack waited outside, earning just as many looks as he had while waiting at the Diary Queen before for Sora and Rinoa, but minding just as little. He pulled out his compass and watched the direction it was pointing, assuming that Delphine was none too far from its reach.