Chapter Text
I have this thing where I get older but just never wiser.
I wake up screaming from dreaming
One day I'll watch as you're leaving
And life will lose all its meaning.
Anti-Hero: Taylor Swift
The sight of St. Mary’s Island port always induced anxiety within Jack. Although one of the safest places for him and his pirating comrades, Madagascar held more than the feeling of security. It was an island of mixed-up emotions that he insisted on returning to regularly. Jack had never claimed to be the smartest man in the room. Sometimes, he was quite stupid, and this trip was proof of that stupidity.
“Well,” Mr. Gibbs huffed. “How do you reason it'll play out this time?”
Jack gave his first mate the fiercest side-eye he could manage and scoffed as they walked down the gangway together.
“Much like the previous time and the time before the previous time, Gibbs,” he answered, swatting away the inquiry with his animated hands.
“And that bodes well for you, does it? Can you manage the inevitable downward spiral that follows your indecision?”
Stopping in his tracks, Jack turned around to face Gibbs. Who told him to bother everyone this morning?
“Master Gibbs, may I remind you that you are under my employ and therefore not at liberty to discuss my personal life choices whenever you see fit? Leave me be, bugger off,” Jack said, waving his first mate away.
Gibbs shrugged his shoulders and quickly made himself scarce amongst the people at the docks. Jack took a deep breath and continued, fully aware that Gibbs had been right to question him but irritated nonetheless. So, he had a point, but what exactly did he expect? A sudden change of heart on the subject? Codswallop, Jack thought. That would get him nowhere, and longing in silence sounded infinitely better than heartbreak, thanks very much. Yet, as he approached the familiar little tavern below the bustling inn that was his only destination on the island, he thought heartbreak and longing both be damned. Damn it all. He'd return to the Pearl, get hideously drunk, sail away, and never return.
Then again, how did one sail away from feelings? Davy Jones had carved out his heart, so there was some semblance of hope. He grimaced and, begrudgingly, marched into Azure Mary’s tavern just as he knew he would anyway. The sun had only begun to set when the Pearl had glided into port, so the atmosphere felt lively but restrained. Jack simply waltzed up to the bar and sat, eager for a drink.
The bartender had his back turned as he lit a lamp to accommodate the growing darkness in the small space, but when he turned and saw Jack, he gave a half smile.
“Jack. The usual?” the bartender asked, already beginning to fill a mug.
“How did you ever guess, mate?”
The bartender slid the mug, amber liquid sloshing over the sides, to where Jack sat.
“You're a glutton for punishment, hu?”
“Caleb, you say that every time, and every time I’ve no idea as to your intention in saying it,” Jack stated before taking two large gulps of his drink.
“Sure, mate.”
Jack turned his head to scour the crowd of patrons, tapping his fingers against his glass in some disjointed rhythm. Several people milled about, sat and drank, and laughed out loud in the dark corners, but he didn't see who he thought he might. His heart fell. He hated the sensation of it.
“She's here, Jack. She’s just stepped outside,” Caleb commented, and Jack spun to the bar.
“Hmm. Thought so.”
“You make it more and more obvious each time you visit.”
Jack resented this, and he pulled back, visibly offended. The audacity of his friends to call him out. They must have met beforehand and planned it together.
“I beg your pardon, but you've horrible service this evening,” Jack scoffed.
“I do try, just for you.”
They stared each other down in mock defiance until Caleb was forced to back down and help another customer. Jack chuckled and rewarded his win with another swig, hoping to be inebriated enough to act normal when he saw her, but not drunk enough to make a fool of himself.
Jack felt a hand rest on his forearm, and in surprise, he quickly looked at the woman attached to the hand. His mind went blank. His body rushed with adrenaline. Her brown eyes made him forget his name.
“Jack!” she said with a smile. “We weren't expecting you until at least next month.”
Use your fucking words, mate.
“Emma,” he greeted her. “Pray tell, how have you become more beautiful than the last time I saw you, hmm?”
Sure, when in doubt, use your famous charm. Usually works.
She rolled her eyes and gave him a playful shove, and he knew at least he'd gotten past the greetings.
“Beauty is relative, and I know a few women whom you've deemed beautiful in desperate times. By your standards, I should fear I'm quite the opposite of beautiful. And, lest you forget, you were here eight months ago, Jack Sparrow. I can't have changed much.”
“By my count, I last visited seven and a half months ago.”
“I actually don't care,” she whispered.
A tendril of brown hair had fallen from her pins and swayed against her neck. Jack nearly dug his fingers into his thigh to keep his eyes from lingering.
“Rude,” he retorted.
“Finish your drink, and then come find me. I’ll take a break. Maybe my brother will be so kind as to allow me a drink during that break,” Emma said, looking expectantly at Caleb.
“You do own half the place, Em. Do as you like.”
Emma smiled again before removing Jack's hat, placing it on her head, and giving him a slight curtsy. Jack didn't fight and allowed her to walk away with his property, knowing he'd fetch it later.
She can have anything she wants.
His gaze returned to his drink, and he tossed his head back to swallow the rest in two gulps, slamming the mug onto the bar when he finished. Caleb stood before him, cleaning a plate and shaking his head in true disapproval.
“Oh, you're so bloody smug tonight, man. Lay off me for once, will you?” Jack hissed.
“Look, Jack,” Caleb said as he leaned across the bar. “I've been privy to your feelings for Emma for some nine years now, and I'm tired of wondering what you’ll do about it.”
Jack did not like the way Caleb was looking at him. His velvet brown eyes, the same as his sister's, peered into his soul in a violating way. It gave him chills.
“Stop that,” Jack said, shifting in his seat.
“Are you going to tell her you're in love with her? Or not?”
Caleb had always been mum on the particulars of Jack and his feelings. After nearly a decade of friendship, the man had never blatantly spoken the word love regarding Emma, but they both knew that's what it was. Now, Jack felt scolded and irritated.
“How about not ?” He asked.
This only garnered a sigh from Caleb.
“Jack, one day Emma is going to settle with some man who waltzes in here and makes her a deal on a good life she would be stupid to refuse. She may be my wild younger sister, but she's a woman, and that's what women must do. She's nearly in her next decade of life, and her prospects are dwindling, but she's already had several would-be suitors knocking at our door.”
“What? Several what?” Jack asked, suddenly very interested in what Caleb had to say.
“You heard me well enough. If you don't pluck up some of your infamous courage and tell my sister how you feel soon , you'll lose her.”
The question Jack needed to ask chased the rum out of his system and made him sick with worry.
“Does Emma have a particular gentleman in her sights? Is she interested in any of these would-be suitors?”
The shrug Caleb offered only made his stomach lurch. What if I waited all these years out of some pathetic fear of rejection, and she's gone and fallen in love?
“I don't know. She doesn't tell me everything. You know her, Jack, she's quick to laugh and keeps her secrets close most times. I haven't seen her with anyone if that makes a difference.”
“It bloody doesn't, but thanks all the same.”
“Take her back to the Pearl, offer her a drink in your cabin, and talk to her. Tell her . I swear I will not allow you back in this establishment if you leave this island without letting her know. I’ll tell her myself if it comes to it. As your friend, I cannot watch you come in here and love her from a distance any longer.”
Jack sighed and lightly banged his forehead against the wood of the bar. If he had known that Caleb would hound him to death about Emma, he would have skipped the visit and gone to Tortuga instead.
“Fuck’s sake. I'm not prepared for that at all.”
“Why not? Hell, nine years should have given you ample time to dwell on how to tell her you love her.”
Jack looked up from his self-pitying state and shook his head at his friend.
“No, no. I never said I hadn't dwelt. I said I'm not prepared. I've dwelt plenty, Caleb. You seem to be under the delusion that I have given little thought about my feelings for Emma. I know what I would say to her, down to every last syllable.”
Caleb pointed to the back of the tavern and smiled.
“Then go do it. I've got a tavern to run, mate. Best of luck.”
His friend left him sitting alone at the end of the bar, infuriatingly sober and panicked. He knew this day would come and yet hoped it wouldn't. Was he going to have to tell her?
Absolutely not.
Why?
She is entirely too interesting and good for the likes of you.
Don't know what that means, but I'm offended.
You're insane and arguing with yourself once again, and she'd do well to stay away from you.
She'd do well to stay close to me. Very close. Close enough to touch.
See, thoughts like that will inevitably bring you trouble.
I was in trouble the second we realized we loved her, mate.
We?
Aye. You. Me. We. Us. Same person. Same feelings.
Bugger.
Jack didn't know if he had successfully fought his doubts or if he had confused himself further, but he pushed away from the bar and resolved to at least find Emma. He had finished his drink, and she had instructed him to find her. He had a historically rotten record of doing everything she asked of him.
He scanned the crowded space again, and although he saw many attractive women, he did not see her. That was until he looked up towards the balcony that led to the inn. His hat was the giveaway. She and another woman were leaning in close to each other, laughing and attempting to hide that fact behind their hands. Emma's companion whispered into her ear, and whatever she had said caused Emma to laugh loudly, no longer worried about keeping it secret. Her laugh had always done a number on him, made him feel as if every horrible thing in the world could someday be righted.
Jack knew when he had caught her eye because she quieted, looked at him, and whispered to her friend again. Then, she rushed down the stairs to meet him, parting the crowd with ease as if everyone knew she owned the place. And she did.
“I've decided I'm off for the evening,” she said once she reached him. “Caleb and everyone else can hold down the fort, as it were.”
“Meaning I have you all to myself for hours?”
“Scandalous! I'll allow it. What's our plan, then?” She asked, looping her arm through his.
“Tis entirely dependent on what you'd like, luv.”
“Well, I would not complain if a drink were presented to me, but not here. I'm always here.”
It was as if the plot Caleb had suggested was writing itself. Jack, uncomfortable, nervous, and desperate, thought he may start with the easiest part of it all. It was just a drink, and that did not mean he was confessing anything to her. Clearing his throat, he leaned closer to ensure she heard him through the noise.
“Might I suggest we have a drink aboard the Pearl?”
He watched as her eyes lit up at his proposal.
“Oh, can we?”
“Aye.”
Emma kept her arm looped through Jack's as they walked from the tavern toward the docks in the dark. He couldn't tell if she led him or if he led her down the path, but he wasn’t complaining either way because he was happy just to be there.
No one would have believed Captain Jack Sparrow had fallen in love, least of all himself. He often pondered how he ended up in the mess of it all, particularly on nights when sleep evaded him, and all he had were his thoughts and maps. Jack could always pinpoint the moment he lost his goddamn mind over Emma but had never been able to reconcile his flighty nature and his want to hold onto her forever.
A decade ago, he had found himself at St. Mary's Island, searching for a place to lie low during a time when his wanted posters were plastered from England to the Caribbean. He needed to garner little to no attention. He liked the notoriety but needed to stay out of sight for as long as possible. Jack had found the combined tavern and inn tucked away from the docks and had been welcomed by Caleb and Emma Page without incident. They allowed him to stay on, paying weekly, for an entire year to ensure his safety from the East India Trading Company, the Royal Navy, and personal enemies. It took very little for the three of them to become acquainted and friendly, and Jack found that he and Emma meshed well without any work. It was entirely natural between them. He considered the siblings his close friends, which meant much more to him than they may have realized.
There had never been some grand awakening about Emma’s attractiveness- she was, in the simplest terms, very pretty. He had thought about seducing her and having his fun early on but found that when he envisioned doing so, it never quite felt right. Of course, it appealed to his urges, but he liked and cared about her. That should have served as his first sign. They had fun, spent hours talking while she tended the bar, and laughed at each other's jokes. His favorite moment with her included a belligerent drunk who’d made quite the scene one night. Emma threatened the man, and the threat came at the end of a blade that Jack had no idea she knew how to use or where she kept it. She only used it for show, she claimed, once the man retreated into the street, but she knew full well how to handle it.
Emma looked after his room maintenance, slid him free drinks in the middle of busy evenings, and frequently toured the markets with him. Jack found himself enamored with her eccentric disposition, the silly and unabashed personality that lured customers in but seemed to confuse the men who may have shown her interest. People said Emma obviously could not be beautiful, intelligent, and funny. Women had to choose one and stick to it. But Jack knew Emma and knew she was beautiful, intelligent, funny, kind, and too good for those who would look down on her for being a well-rounded human being. Emma had the unique position of freedom in her choices. She had her flaws, of course. She never gave away information that may hurt her and was cheery to a fault.
After nine months, Caleb pulled Jack aside and pointedly asked him if he had feelings for Emma. The question had shaken him. He had no feelings, he insisted, none whatsoever outside of friendship and mutual respect. He kept the fact that he was insanely attracted to Emma out of his explanation. Caleb, however, told Jack that no one believed him, and to sort himself out or leave. For days, their interaction lingered with him. It haunted him. What exactly was he supposed to sort out? More importantly, was there any merit to Caleb suggesting feelings were involved?
As Jack soon found out, there was merit, much merit indeed. He had always thought of “feelings” as a confusing term; contrived and ubiquitous. It meant nothing. On the other hand, he also thought romantic love was always realized after a cosmic happening between two people. As if a bolt of lightning had to strike at the perfect time, in a dramatic flair. Jack Sparrow had been wrong on both accounts.
All it had taken for Jack to effectively lose it all was the touch of Emma’s hand. It was uncomplicated; Jack's hand rested on the bar, and as Emma passed him to serve another patron, she gently reached out and touched him. It had been just her fingertips on the back of his hand, a tiny stroke of her skin against his. It had been more than enough; it had been everything. By the time Jack dared to peel his eyes away from their point of contact, she had moved on, but he knew he never could. He knew he was in love with her, that he had been falling for her for months, and that meant he had to get the hell out of Madagascar.
Yet, he never stayed away too long, but by God did he try. He would get out, have his fun, face danger, make a profit, and sleep with strangers, but he inevitably turned back up to see her. Each time, seeing her did nothing but make him love and want her more. With his feelings so encompassing, he knew there was no coherent way to tell her how he felt. And, he resolved after a few years, he was a fucking coward.
So there he was, older but not wiser regarding her, wondering if he would confess it all, make a mess of it, or deal with Caleb’s ultimatum. All choices were his least favorite.
“You've said nothing about your hat still gracing my head,” Emma said.
“Mmh, I'll need that returned to me. But have your fun,” he chuckled as they reached the docks.
“I may return it. I may not.”
They swerved around crates and barrels, watching their step as they approached the Pearl . Emma looked up at the massive ship and smiled, and Jack saw the change in her features, something close to admiration, he reckoned. They stepped up the gangway, and once they came to the deck, Emma immediately set her hands along the railing and sighed loudly.
“She’s such a beautiful ship, Jack. You're lucky to call this place home. I've always envied that.”
“She's done me well. Sheltered me too many times to count.”
Gripping his hands to the railing as well, he felt his fingers close to Emma's as he breathed deeply. He loved the reactions of others when they boarded his ship. No one ever found themselves disappointed, least of all Emma. Even if she had, she would have never made it known. Every time he brought her, she marveled at something new.
“About that drink,” she said, tapping her fingers against the dark wood.
“Aye. In my cabin, I should think. Privacy from all the movement of the crew as they mill about.”
No ulterior motives here, luv. Certainly not so I can have you alone for at least a short time.
“Lead the way, Captain.”
“I believe you know the way, dear.”
Jack stretched his arm out and motioned her to his cabin, slightly bowing. The ceremony, the production of it all, made it easier for him to bite his tongue when he knew what he wanted to say was not in his best interest. Dear was comfortable, an endearment a friend would use. What he wanted to call her was darling , as he found the term far more intimate and sensual. Stupid really, that he shouldn't have just called her what he wanted. It had never stopped him from doing so with other women. It was just a silly word.
Emma smiled coyly, fighting a laugh as she headed for his quarters. Jack followed behind, watching the slight sway of her hair beneath his hat and wondering how women kept it all pinned in place so masterfully. It seemed torturous and uncomfortable, but damn if it wasn't pretty. Emma reached his cabin doors and politely stood with her hands behind her back, waiting for Jack to open them.
“Afraid of something in there?” He asked teasingly.
“I didn't wish to enter without your permission.”
He swung one door open and leaned to whisper to her before stepping inside.
“You always have my permission, luv.”
Her footsteps echoed behind him as he opened his second set of doors. Once inside, he held the door open for her. The lamps were lit, and he knew Gibbs must have just been there going over logs. Less work for him.
“Welcome, my lady, to Le château amusant de Jack,” he said with satisfaction.
“Well, I thank thee, sir. However, I believe grotte may be the correct term.”
“Cave of fun does not sound fun. That sounds debaucherous, which I have just now realized… may indeed be fun,” he mused, closing the door.
Stepping around her, he walked to a small liquor cabinet built into the cabin wall.
“What’ll it be, Em?” He asked.
“I would love some mead if you have any.”
Jack looked over his shoulder, bewildered.
“Course I do! You think I'm uncultured?”
“Most likely. Half uncultured at the most, though.”
Chuckling, he turned back to his collection, thumbing through his options, the clinking glass grating on his nerves, until he found what he was looking for.
“Ah, just the thing,” he exclaimed, pulling the mead and two glasses from the cabinet.
He showed his objects to Emma, and she smiled widely, accepting a glass. He pulled the cork out theatrically with his teeth and filled her glass with amber liquid.
“Thank you,” she said, and he nodded.
Jack poured himself a drink before setting the open bottle on his desk with a thud and raising his glass to her.
“What do you propose we toast to?” He asked.
Emma contemplated before raising her glass and declaring, “To subverting the expectations put upon us by weak men in power!”
Jack laughed, caught off guard by her choice.
“Hear, hear! Well said, my dear.”
They tapped their glasses together, and Emma was quick to take a drink. Jack, however, took a few seconds to watch her, appreciating the moments he could blatantly stare without risk of being caught. He didn't draw it out and took a small sip of the mead as he looked away. He had yet to decide what would take place in his cabin between them, but for now, he only worried about making her happy and comfortable.
“That's delightful,” Emma said as she removed his hat and set it aside. “I don't think we serve this. It's so hard to import now.”
“No, you wouldn't. It's an old bottle made especially for me.”
She raised her brows and took another sip.
“Well, thank you for sharing.”
He waved her comment off as if to say, ‘ No thanks needed’ and leaned against the wall.
Emma stepped around the desk and rooted herself in Jack's chair with a sigh.
“I like the stillness in here. The tavern can become so loud, I sometimes think I'll go deaf.”
Jack liked the optics of her at his desk. She looked authoritative like she belonged there.
She belongs in many places in this cabin. The bed, against the wall, perhaps right in that chair with me on my knees.
“Hmm. Aye. Built to be as quiet as possible, I'd imagine.”
“Yes, I suppose.”
They both took drinks in unison, and Jack wondered if he'd even have an opportunity to say anything about his feelings given the dry conversation. Not that he had decided either way. Emma leaned her head back and closed her eyes, her balletic fingers reaching to blindly pull at the collar of her shirt that had folded over the incorrect way. Jack swallowed his desire away and decided to speak to keep himself busy.
“Caleb told me you'll be in your thirtieth year in the next few months. Can't have known you that long, can I?”
She opened her eyes and groaned.
“That was quite rude of him, giving away a woman's age so carelessly. Particularly his sister's.”
Jack knew she was joking, but he had also seen the slightly embarrassed look on her face.
“Is my age shocking to you?” She asked.
“No. The passage of time is shocking, luv.”
“Hmm, yes. Well, it is a thief, time.”
She took a long drink and drained her glass. Jack quickly reached over and refilled it with the open mead bottle.
“Thank you,” she laughed. “My thirtieth year. God, I became a spinster long ago, didn't I? May as well join a convent and be a nun. If only I had virginity in my favor, that’s never coming back.”
And hide away your beauty behind a black sheet? Save love for some unfavorable deity? That would be a travesty.
“Why should you? Caleb also informed me that you've had your share of suitors recently. Spinsters do not have suitors.”
“Damn, what did Caleb fail to share with you? I should have a word with him.” She drank again. “I would not call these men suitors. They're all my grandfather's age, widowed, and they do not know me.”
“Surely not all of them.”
“Well. Mostly. The rest are dull.”
“So you've not found a man to your liking?” He asked, refilling his glass.
“I don't quite understand the question. I've found many men to my liking.”
“Don't be obtuse just for the sake of it, dear. Is there a particular man for whom you have feelings?”
He felt his heart drumming so hard against his ribs that it nearly hurt. He tossed his drink back to calm himself down. He'd gone and asked a question he couldn't unhear the answer to, a question that may take him down the path of confessing everything to her. How he would react if she said yes depended on how well he could hold it together.
“Ah. You want to know if I'm in love.”
I don't. Forget I ever asked.
“If that's how you interpreted my question, then yes.”
Emma smiled at him.
“Why are you interrogating me?”
“I'm not,” he scoffed.
“You are! As if I would tell anyone my secrets while sober, Jack Sparrow. At least get me drunk,” she teased, sipping her mead.
She hadn't denied it, which made him want to toss up his mead all over the deck. Surely, she would have denied being in love if she was, in fact, not in love with anyone. Maybe they both needed to drink past their inhibitions to converse honestly.
“Alright. I can make that happen.”
Her eyes narrowed playfully, and her fingers tapped against her thigh.
“Alright. But I will not be the only one asking questions. It would be unfair and not at all advantageous to me.”
Smart girl, don't let me have all that power over you.
“Why should I divulge anything? When have I ever been fair?” he asked with a half smile.
“Oh, don't utilize your tough pirate captain act!” She laughed as she spoke. “You've been fair more times than not, at least with me. A question for a question. Those are the rules.”
“Who put you in charge, luv? I didn't vote for you.”
“It's a monarchy. There is no vote,” Emma said softly before drinking.
“Oh, beg pardon, Your Excellency,” Jack said with a low bow. “Whatever you decree.”
“A question for a question, or questions, whichever happens.”
Jack righted himself and pondered her proposition, biting his nail out of habit. What answers were worth giving to know if she loved some other man? And to what end? Decidedly, he could not risk his biggest secret just to receive the answer to his little question. He would be forced to open up to a heartbreak unlike anything he'd ever experienced if she said yes. If she said no, well, same outcome. Then came the question of who answered first. Would he be forced to tell his secret before she answered his original question? Emma rarely opened up so blatantly, he knew this. This was an opportunity he may never receive again.
“Well?” She asked. “Do you want to play or not?”
“We must have a few more guidelines,” he said, pushing away from the wall to pace. “Who goes first?”
“Well, you asked first. Reasonably, I would answer your question, then ask you a question in return.”
Oh, thank God. There's less risk if she doesn't know what to ask.
“Very well. Then there's the matter of how much information we give per question. I propose we only answer what lies in the question. No long elaborations. Unless we want to.”
“Fair. Then comes the matter of questions we are not willing to answer.”
Jack stopped his pacing and turned to her.
“I would never force you to tell me anything you're unwilling to, Emma.”
“I know, and I would not force you either.”
He cleared his throat, and the bottle of mead caught his attention.
“I have an idea. When we decline to answer, we take a long drink meant to speed up the drunk part.”
Emma’s eyes quickly flashed to the liquor cabinet and then to Jack.
“Perfect. I'll have you know I can hold my drink quite well.”
“I'm well aware. As can I.”
Her smile defined the curvature of her cheek, and she shrugged.
“Good. I agree to the terms.”
“Aye. Same.”
“Well then. Ask your question again.”