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Jack is terrible at keeping people. It's easy to pull someone in, to steal a heart or spark a dream, and Jack loves them for a time before he leaves. He moves with the tide and any who fail to move with him are left behind. He will welcome those who catch up, but most fade into fond memories.
He isn't expecting anything different with Will and Elizabeth. They're young and bright and burning - a slightly doomed love story for the ages. The kind of story that he can share over a drink to entertain, but never be believed.
Which is why, when all is said and done, the visits surprise him. Not the fact that Elizabeth has decided to reinterpret the rules of the curse as a simple inconvenience - she's learned how to take what she wants. If her husband cannot meet her on land, she will meet him on the sea. Not the fact that Will is willing to indulge his wife as she spits in the face of what should separate them and that, so far, they haven't seemed to trigger any tentacle-y reprisals.
But the fact that somehow, he's managed to keep them. That it's easier for them to meet on the Pearl than anywhere else, and it's as much about seeing each other as it is about seeing him.
(Elizabeth had explained at some point, something about the Pearl being pulled from Davy Jones' locker twice, but Jack is hard pressed to remember the rest of it, given that she'd been sitting on his lap and Will had been dragging kisses down the back of his neck, all three of them naked as they day they were born. He'd had other things on his mind than outwitting curses.)
Jack is too old to have his heart flutter like a young maiden in love, but he can't deny he feels something when Will smiles at him crookedly, or Elizabeth sighs his name. He looks forward to their visits but it never aches when they leave, because he knows they'll be back, drifting in and out like the tide.
They've become a part of him the way that the ocean is, a guiding current that pushes him deeper in a way that should be dangerous, but only manages to feel like freedom.