By the by, know full well I'm going to kick my own booty for putting my 2 cents worth in--it just seems like a good idea at this time.
Jack=pirate
AnnaMarie=pirate, now fisherperson
Elisabeth=high born lady, now pirate
Will=blood, pirate, blacksmith, now pirate
Jack + Will=loyalty for whatever DadWilliam Bootstrap Bill, did for a much younger Jack. They had history prior to and begin of Jack's captainacy of the Pearl. Bootstrap did something to stand by Jack, maybe he feels debt owed.
Jack + Annamarie=sailed together prior to Jack losing the Pearl--and yeah, if they didn't they certainly should've--goes without saying she probably had more than a passing fancy for Jack and maybe Gibbs. She's too young to have been around much more than that. I get the feeling she's younger barely than Elisabeth, got a lot more miles.
Jack stole her boat--he didn't distract her with clever card tricks.
Sweet mary michael--Miz Kateloves got it--rock and roll never dies, (yes, old hippie&proud, well, another story) availability and inclination of pirate partners. Jack's the trickster--he does love and care for others, and he is that larger than life 'coyote'.
I think, for my part in the telling, men gotta get there first...women, we don't care until we are the last and only--any man of that time, that occupation, would have had partners--Jack's saving grace in all this is his ability to romance the pants, not plunder the panties.
And whatever ship, well, darlin's, we all know that if'n we'd a been there and he showed up to ask us to 'dance', well, we'd be making the effort to kick up our heels. Love to say I'm not a victum of flesh, however affordable decadence has always been a good thang.
I strongly believe there was a very interesting relationship between the two and that he did a few ladies of Tortuga--he's a man, such is life then and mostly now. Again, sorry, seemed okay at the time.