Chancing Fate - Jack Sparrow x OC

Interlude - Chapter 1

A/N: Welcome to the updated Interlude. This was previously just journal entries to account for the passage of time. Which has now been massively expanded. Enjoy!
Updated 7/22/26

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Breakfast had become one of the few parts of ship life Caroline genuinely enjoyed. During the last month she'd fallen into the habit of sitting beside Anamaria, neither woman possessing much patience for the louder conversations farther down the table. Easy conversation filled most mornings while one or the other mended clothing or sorted through whatever small tasks had accumulated, and today proved no different as Caroline worked another careful stitch through the sleeve of her dark blue jacket.

Anamaria noticed almost immediately. Her eyes drifted from her tea to the fabric beneath Caroline's fingers, amusement slowly creeping into her expression. "Still say he stole it," she remarked with obvious satisfaction, earning a soft laugh from Caroline, who barely glanced up from her work as she guided the needle carefully through the seam.

"He said he won it. Or bartered for it. Something along those lines." Caroline smiled despite herself, though Anamaria only snorted quietly into her cup and shook her head in open disbelief before dismissing the distinction entirely.

"That's pirate for stole it," she informed Caroline with complete confidence, drawing another quiet laugh as her fingers continued turning the sleeve over with obvious approval. Eventually Caroline surrendered with a smile and a quiet, "Mostly," which immediately earned a satisfied grin from Anamaria as though she'd won some private argument and expected nothing less. The woman rubbed the fabric lightly between her fingers before nodding with approval.

"Thought so. Pretty thing, though." Her attention lingered on the jacket while she reached for her tea again, and Caroline instinctively smoothed the sleeve beneath her palm with quiet satisfaction.

It really was. A matching ribbon held part of her hair back now, while the boots resting beneath the bench had long since replaced the pair that had nearly ruined her feet during the first miserable week aboard. Even the comb tucked safely into her pocket had been one of Jack's strange acquisitions. None of the things had been expensive and few of them matched, but they simply kept appearing. Trousers after she'd torn the only decent pair climbing rigging. Blouses because Jack had declared two shirts a tragic state of affairs. A ridiculous assortment of ribbons because he'd somehow decided she owned none.

And then there had been the dress.

Her needle slipped. Not enough to prick her finger, though the smile threatening at the corners of her mouth nearly made her miss the stitch entirely.

Unfortunately, Anamaria noticed. Pausing with her cup halfway to her mouth, the woman regarded her over the rim with entirely too much amusement before finally asking, "What was that?"

"Nothing," Caroline answered far too quickly, lowering her eyes again as she returned her attention to the sleeve.

The response earned nothing more than a thoughtful hum from Anamaria.

Caroline narrowed her eyes, abandoning the sleeve in her lap as she finally looked up again. "There was definitely something."

"Course there wasn't," she assured her with complete innocence, though the smile tugging at the corners of her mouth ruined the effect entirely as she continued watching Caroline over the rim of her cup.

Caroline only shook her head, her attention already drifting back to the dress despite herself.

"Funny thing," Anamaria remarked after a moment, drawing her attention back. Lowering her cup again, she studied Caroline with amusement dancing in her eyes. "Man wears the same shirt until it's near fallin' apart, but somehow notices when you've no proper boots."