DISCLAIMER: I unfortunately do not own Pirates of the Caribbean.
Also, a little history lesson. Upon watching the fourth installment of the franchise, I realized how much alike Angelica Teach and William Turner are, in aspects that will become more apparent as the story unfurls. So I wondered what might happen if they were to meet, and there you have it, the backbone of the story.

The title of the story is taken from the Nirvana song of the same name.
The title of the first chapter is taken from the Neil Young song, 'The Losing End (When You're On).'

CHAPTER ONE:

When You're on the Losing End

"Elizabeth," he started tentatively, "it'd taste a lie to say that things feel the same between us. You've been acting strangely all day; is there something… wrong?"

It had been ten years since William Turner had last seen his wife. He had been out on the untamable waters, controlling the Flying Dutchman and all of the duties that were synonymous with it, and he was bound by his obligations to usher those deceased at sea to the other side. Will was granted one day per decade to walk upon the shores to see his beloved Elizabeth Swann, and the previous visit had led to the conception of their son… whom both parents had seen fitting to dub as Jack. Elizabeth had sent Jack to a boys' boarding school in London, determined to see him an erudite and successful man, and she had quickly grown weary of the tedium and loneliness that surrounded the wretched island on which she resided.

"Will…" she shifted uncomfortably, tugging on the fluffed white sleeves of the loose-fitting blouse she wore. "It's… it's just so difficult… being held captive by this piece of land."

Will smiled in his warm, charming manner and asked, "Is that all? You have the Empress; you don't have to stay here. Only a day every ten years, the same as for me."

Elizabeth didn't return the gesture of cordiality. Her dark eyes locked his in a solemn grip. "It isn't a matter of having a ship… it is a matter of having no place to go. I find myself on deck, on the waters, and yet I don't feel the rush and the freedom I used to… because the freedom no longer has a purpose. Don't you see? There is no more excitement in it. My father is long gone, Norrington along with him, and I see my husband but once a decade. Our Jack is off at school, which is best for him, but I have nothing of substance with me any longer. I feel useless, Will, and I'm losing my mind."

"What are you saying, Elizabeth?"

"I'm saying that… ever since… it happened… this has felt more like a burden than a marriage."

Will's face blanched, and if he had had a heart, he was sure it would've temporarily stopped beating. His eyes darted around all areas of her face, trying to fully comprehend what he had just been told. "Of course it has, but we love each other, and that is what shall get us through the years. One day with you is worth more than eternity with anyone else! That is… you do still… love me… do you not?" William finally asked, exasperatedly.

Elizabeth sighed and looked off into the distance before returning her gaze upon her husband. "Of course I do… I always will. But I am not the same woman I was in the days of Port Royal. I can no longer pretend that these saccharine emotions and these quixotic expectations of ladylike behavior are what attract me. The Black Pearl taught me the importance of freedom, of independence… and I've been torn from what is now most important to me."

"Are… are you saying that… you want this to end?" Will inquired tearfully, struggling to form the words he could never accept. His life had revolved around Elizabeth Swann since he had first met her; since they were both twelve years old. He understood that waiting for him had taken its toll on her- how could it not? -but he could not understand how she could give up on what they had. Had she expected the transition into this unconventional lifestyle to be seamless?

Elizabeth looked down at the grains of sand, unable to look at the emotional damage she was inflicting upon the man she loved. "Yes. Will, it has to. You're immortal. I am not. At one point you will be without me, and it will hurt less when my time comes if we separate now, anyway."

"When your time comes, you will be sent to the Dutchman, and we will be together every day for as long as this earth lasts. Please… you can't do this, Elizabeth," he pleaded expressively.

Against her will, Elizabeth, too, began to gently cry. "Look at me, with my culminating depression tying me down to land. When my time comes, I will not be at sea. I'll be here, and that means we will not be together."

"Then… this is really it, isn't it? After all we've been through, this is what ends it?"

"Yes." What more could she really bear to say?

A bitter flash danced across Will's dark eyes. "Is this about Sparrow?"

Elizabeth paused, thinking of Captain Jack Sparrow, the complete antithesis of her husband. There had been a time when she wanted to have nothing more than the captain to herself, in her arms, for they were very much alike: craving freedom, adventure and spontaneity. But those feelings of desire had been so deeply repressed that she could no longer admit them to herself. "No. This is about us."

The couple allowed a few minutes of silence to wash over them, until Will asked, "Is… is there anything I could've done- or could still do!- to have prevented these feelings of oppression?"

"I'm afraid not," replied Elizabeth, looking apologetically into his eyes. "We both did all we could in this dreadful situation. Neither of us asked for it, and I cannot tell you how sorry I am to only be adding to the hell you are forced to deal with."

"I understand…" he said sorrowfully. He did understand, and a large part of him had been expecting this. Their letters of correspondence had long lost their ardor; Elizabeth's eyes hadn't shined upon his arrival, nor had her beautiful smile showed the genuineness it had in the years gone by. Will was not surprised- but still unbearably wounded- and asked, "As for the chest? My heart still belongs to you, even if you do not wish to possess it."

Elizabeth's own heart shattered as the words left his lips. "I think you should have it. It shall only serve to remind me of the ways that I have abandoned you."

Will nodded somberly. "Then… then I'll beckon my father to raise the Dutchman as soon as possible."

"That may be for the best."

"I love you, Elizabeth. I'm so sorry for-"

"Don't apologize," she interrupted. "It was Jones's doing. But I love you too… Captain Turner. Always have and I always will."

With one last kiss, the couple bade each other farewell, neither of them quite believing what had just transpired.