Discalimer: i dont own anything to do with pirates of the caribbean.

A/N hey! another one shot... enjoy...

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Should of, could of, would of...

Jack rubbed his temples, screwed up his eyes, and growled in frustration. There was nothing that he could do as far as he could see. What was done was done... wasn't it? He couldn't change what had already happened. Sighing Jack leaned back in the chair he was sat in, and put his feet up on his desk, with a bottle of rum in his hand. Closing his eyes again he started to think trough a series of events that led to the utlmite loss for him... and he hadn't even know what had been happening until it was to late.

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Should of...

I should have told her. Why couldn't I have just spilled it? I thought I had made it obvious without actually saying the words. Didn't think I needed to. I thought women were supposed to pick up signals. I was sending them out wasn't I? I should of made it more obvious to her, show more. Made my actions a bit more... I don't know.

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Jack heaved a heavy sigh as he began to remember parts of their last conversation.

"Ana, I should have told you."

"Yeah you should of." Jack closed his eyes, he hated it when she was angry, but it never lasted long... usually.

"Don't." Jacks eyes scanned her face, trying to get eye contact but she wasn't having any of it.

"Don't what Luv? I'm not doin' anything."

"That! Trying to made me look at you and forgive you, its not going to work, not this time." Jack brought his hand up to her cheek but she slapped it away.

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Jack swallowed hard, as his face showed signs of regret.

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Could of...

I could of told her. I might of thought I made it obvious, but I didn't did i. Not enough anyway. All the time I was alone with her, I could of told her. I think she was even waiting for me to, wishing I would. Why was I so stupid... that's Will's job not mine. But I seem to have made a better job of it then him...

Jack put his hand over his eyes as he remembered the next part of the conversation they had...

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"I thought I made it obvious... I thought I shouldn't have to say it." Ana looked up at him, scowling.

"Well you didn't."

"I suppose I could of made it a little more..."

"No you should have just told me." Jack looked down at the ground.

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Jack got up from his chair and walked outside, looking at the sunset that was painted across the sky.

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Would of...

I would of told her. I kept telling myself... 'Wait for the opportune moment.' But when I came I did nothing. The opportune moment... sitting looking through the logbooks, maps and all the other papers, first mate and captain were supposed to deal with, I'd just wanted to lean over and kiss her. But why didn't I? Oh yeah, she aught my eye and I looked away.

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Jack looked at the orange, red and yellow swirls that were dotted on the dark blue sky.

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"I would of..."

"What when the opportune moment came? Get real Captain Sparrow." Jack winced as she refused to call him by his name. She only ever did that when they were mucking about or she was mad with him.

"Yes. But I didn't when that came. I let it pass. I'm sorry Ana, but you know now. Can't we jest forget about it? Move on?" Ana laughed.

"I don't think so. Jack you let me fall for someone else, then you let him kill himself, all because you were jealous. I... I can't forgive you for letting that happen. Sparrow you owe me a ship and I want it now."

"Ana..."

"If you meant, what you said, you'd do this for me. I don't want to go, but I cant stay either. Just let me go..." Ana had tears in her eyes as she pleaded with him to give her, the ship he had owed her for over 6 years.

"First thing we'll get ye your ship Savvy." Ana nodded, turned and left the room leaving a hurt captain behind.

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Jack sighed, and looked up to see Gibbs coming on deck, looking away again he looked back to the sky.

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Why?

Why did I buy her that ships this mourning? Why did I let her go? I'm more of a fool then she thought... then I thought. I shouldn't of, couldn't of... wouldn't of... if she hadn't of looked so sad here and so happy looking at her new ship. Sacrifices made to keep her happy... jest a shame I wont be anymore. Since when did my life get so... un-simple?

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"Alright Captain?"

"Aye."

"What's wrong?"

"Too much thinkin'. A'int good fer me." Jack walked back towards his cabin, picking up another bottle of rum on the way.

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A/N what do you think? Please review. if people review I might add another story to go with it, 'cause I have an idea that clicks into this one... but only if peeps review. :-) Suzy xxx