Hi Lottie! So, you may have talked about this before and I just haven't seen it, but I have a biased interest, so could you tell me about Jack's relationship with Tia Dalma? I haven't read TPOF (yet), so I don't know if it goes into that more, but I'm curious and I always like reading your metas. :>
ahhh of course fae!! i haven’t talked about them in a while but Jack’s relationship with Tia Dalma is one of my absolute favourites in the entire franchise because of how similar they are at their core, so i will happily ramble about them for a little while! I’m also gonna refer to her in this predominantly as Tia Dalma rather than Calypso because that is how Jack knows her for the majority of their relationship ( Jack doesn’t find out for sure that she’s Calypso until he overhears hers and Barbossa’s conversation in AWE before the Brethren meeting, but he absolutely has his suspicions about her before then )
TPOF doesn’t actually add a huge amount regarding their relationship ( Tia Dalma doesn’t appear in it but Jack mentions her several times and seems to have this fascination with/crush on her at this point in his life ), but along with the young Jack Sparrow books it confirms that Jack has known her since he was a teenager. he also has his compass in the Shipwreck chapters ( set when he’s 20 years old ), so we know that Tia Dalma gave it to him sometime before that. regardless of my own headcanons concerning Jack’s mother, we also know that Jack has no maternal influence either in TPOF or any other media since she was effectively banned from being mentioned by the House of Mouse themselves, which is why I think Tia Dalma in some part fulfils that role for him. so the easiest way to define the relationship that Jack has with her in my opinion is as this slightly unorthodox mix of maternal and intimate
they are absolutely intimate and have slept together at least once before AWE ( more than likely pre-CotBP but post-mutiny, if I had to pin it down in his timeline ), which is indicated not just by the flirting but by the throwaway line in AWE about Tia Dalma being one of the four people that Jack accuses of trying to kill him in the past ( the other three are Barbossa, Elizabeth, who succeeded, and Will ). when Jack addresses her directly, she says:
“Don’t tell me you didn’t enjoy it at the time.”
“Fair enough, all right, you’re in.”
the innuendo of this whole exchange implies that the occasion Tia Dalma tried to kill him was during sex and likely kinky af lmao. it’s also safe to assume that after this particular incident, Jack gives her a wide berth for some time seeing as, in DMC, he’s very reluctant to seek her out and, when Gibbs says that he’ll watch Jack’s back, Jack’s response is ‘It’s me front I’m worried about.’ again, innuendo that implies these two were sexually intimate until a point where Jack was subsequently scared off. but I don’t think this is a simple friends-with-benefits sort of relationship, at least not for Jack ( you can debate Tia Dalma’s attachment to Jack but I truly do think she is fond of him in a way that she is fond of very few humans, even in spite of his connection to the Brethren Court, considering her petname for him and the way she acts around him ). it’s not love either, at least not in the traditional sense of the word in a romantic context, but this is where Jack’s feelings get complicated because of that maternal aspect to their relationship
I think Tia Dalma’s influence in Jack’s early, teenage life is very formative for him. you only have to look at TPOF to see how he references her a fair bit in relation to not just the situations he finds himself in ( anything faintly supernatural = oh yeah like tia dalma lmao ), but also in how Jack approaches relationships and I think this is the big one. for someone who grew up on Shipwreck Cove where the main exposure to women Jack would have had would likely be the sex workers operating in the island’s brothels, and the only exposure to relationships would be that between the sex workers and the sailor clientele ( plus the sailors he’d know who had wives and children in some port somewhere ), knowing a woman like Tia Dalma, who is powerful, untameable, takes multiple lovers and desires freedom above all else would be very important in shaping who Jack ultimately becomes in his adult life. he talks about this in TPOF too:
“Tia Dalma isn’t ‘mine,’ love,” he corrected her. “She’s her own woman, make no mistake. No man will ever possess her. She’s…” he groped for words to express something indefinable he’d always sensed about the hoodoo sorceress. “She’s…she…sometimes it seems like she wears her woman’s body…the way you would wear a gown.” He shivered. “She has power,” he said. “Real power. She’s no one I’d want to cross.”
also -- and i know these headcanons are kinda shot down by Teague’s presence in AWE and canon established in TPOF but -- it was always my personal theory that it was Tia Dalma who first fashioned Jack’s hair into dreads and introduced him to kohl, plus that she was the one Jack brought the liberated slaves to when he went rogue from the EITC --- and I really wish TPOF had gone that route rather than ignoring that obvious scene at the very end of DMC where the remainder of the Pearl’s crew return to Tia Dalma’s shack and the river is full of what look like ex-slaves/maroons who are holding candles in vigil to Jack ( it also adds a whole other dimension to the scene when Jack first arrives at Tia Dalma’s shack and is looking rather on edge at the faces staring at them in the rowboat from behind the trees, but i digress ).
then there’s the compass ( we’re ignoring how he got it in DMTNT ), and even if we don’t take into account the weird powers that DMTNT’s script gifted it with, it’s established in TPOF to be a very powerful magical object. Tia Dalma gives this to Jack when he is a teenager. it’s clear that either she knows Jack well enough to know the real him very well, or that she sees enough of his destiny to trust him with something like that and agree to trade it.