Disclaimer: Sadly, I do not own anything related to Pirates of the Caribbean. Well, except a Jack Sparrow poster, but that's pretty much it. Only original creations (characters, places, etc) are mine.

AN: Here's my new story, starring our beloved Captain Jack! Please note that, in this universe, Pirates 2 and 3 never happened, which makes it easier on me to obey the funny voices directing this story in my head (wink). Enjoy, and please review!

Chapter 1: What's a Pirate To Do?

"Face it, Jack," Gibbs said, handing him a cold damp cloth. "You've lost your touch."

Pressing the rag to his cheek, Jack glared at him. "If you value your pay, Gibbs, you'll not say that again."

Given the circumstances, however, Jack had to somewhat agree with his first mate (though he'd never admit it aloud).

As it was, Gibbs chuckled and fetched a bottle of rum, which he pressed into his captain's other palm. Jack winced as he removed the cloth and took a deep drink, hoping the alcohol would soon numb the sting that still lingered in his cheek. He was lucky the fellow had been thoroughly drunk and only managed to clip his face, otherwise he'd be missing a few teeth rather than bearing a bruised cheek (and matching ego).

"You should have known the lass had a man somewhere," Gibbs proceeded to lecture him. "A girl that pretty in a town like Tortuga always has a man or two up her sleeve, whether you see her with them or not."

Jack took one last gulp of rum and set the bottle down onto the table. "Aye, but I'd have thought that the man would be entertaining himself elsewhere. Besides, she was willing enough, wasn't she?"

Gibbs shook his head. "You've never had good sense when it came to women, Jack, especially when it came to your nightly acquaintances." He eyed his friend carefully as he turned to leave. "Perhaps it's time for you to finally settle down with one woman –at least that way you'll be able to have company with you every night for sure."

As the cabin door shut behind his first mate, Jack's eyes narrowed in thought. Settle down? Captain Jack Sparrow? What a ridiculous idea! After all, he had a certain reputation to maintain, and how could he do that as a married man? And even if he did wed a woman who didn't care about him finding pleasure elsewhere, he would no doubt get another reputation, one that was far more unpleasant.

Though the women in Tortuga were known for their low moralities, some refused to bed men who were already married. There was the small bit of guilt the wenches would feel about being with another woman's man, but that was soon gotten over. No, what the wenches really worried about was jealous wives searching for revenge, and in most cases, the wives usually won. Besides, fights caused wounds, and wounds left scars, which tended to hurt a wench's business, hence their caution.

Sighing, Jack took another drink from the bottle and stared at the wall. Lately, his efforts in wooing the ladies of the night had been rather unsuccessful, and he couldn't understand why. Was he, Jack Sparrow, losing his touch in these matters?

He shuddered in horror. If this was so, it could bode very badly for him. A pirate had needs, after all, and without the ability to fulfill those needs, Jack knew he was going to spend the rest of his days being very lonely indeed.

"I'm thinking that marriage might not be so bad," he muttered, looking into the depths of his rum bottle.

However, there was one small problem: Jack wasn't the sort to settle with one woman.

As a pirate, he wanted variety, adventure, and freedom. Marriage meant having only a single woman in his life, and he'd no doubts that she would forever be telling him what to do, where to go, and what he should be spending his hard-earned plunder on.

'Even worse is the screaming and the throwing of objects when she's upset,' he thought, cringing. Women were known to throw things when angry, and some of them had very good aim.

There was the option of leaving his wife in a fine house on an island somewhere, but that would be inconvenient for a man in 'need,' particularly when he traveled around the world, not just the Caribbean. It could be months or even years between visits to his wife, and that was not an option.

No, Jack knew that he would have to keep his wife onboard the Pearl, and even then he wasn't sure if it would be worth it.

Taking another swig from his rum bottle, Jack decided to head to bed. There was a lot to consider, and that was best done after a good night's rest.

Unfortunately for Jack, his problems didn't dissipate with the arrival of the sun. He'd thought that waking up would make it all go away, but the idea of marriage lingered in the back of his mind as he rose, washed up, dressed, and went out to see how his beloved Pearl was doing.

The bright light of dawn promised a beautiful day. Stepping onto the empty deck, Jack took a deep breath, the scent of the sea almost causing him to forget his problem.

'Almost' being the key word.

If they had been at sea, he would put himself to work at doing his duties as captain. As they were presently in port and most of the men were still in town, there was nothing to distract him. And Jack was in desperate need of a distraction.

The sound of someone humming was a welcome one, and the sight of Gibbs emerging from the lower decks with a full bottle of rum was even better. Jack practically ran across the deck, snatching the bottle out of Gibbs' hand and popping the cork to take a swig.

Gibbs let off a curse, then sighed, knowing that he wasn't going to get his rum back. "Didn't have an easy night, did you, Jack?" he asked, giving his friend a concerned look. "Anything you'd like to talk about?"

Jack muttered a negative under his breath, but Gibbs merely sighed again and rolled his eyes. "Then let's head for breakfast at the Faithful Bride, aye?"

The entire walk into town was silent, but the minute they took a seat in the furthest corner of the Bride, mugs of rum in their hands, Jack let his frustrations out.

"I don't understand how this could have happened, Gibbs!" Jack snapped as a wench brought them eggs, bread, and some freshly cooked meat.

He waited until the girl was gone before going on. "I admit to having troubles before, but lately it seems to have gotten worse. What's a pirate supposed to do when he can't even win over a wench for a single night?"

His first mate took a bit of eggs, followed by some meat and a swig of his drink. When he'd swallowed his mouthful, Gibbs shook his head. "Why not do what I told you? Take a wife."

Jack almost gagged on his eggs. "Gibbs, I know that you know that I'm not the marrying kind. Variety is the spice of life, and being tied to one woman is the sort of thing that gets dull very quickly, especially for a pirate."

"Not if you found the right one," Gibbs hinted as he worked his way through his meal. "Besides, you aren't the only one who's in want of female company."

His fork hanging in midair, Jack looked long and hard at his first mate. "Explain," he ordered, putting down the eating utensil.

Gibbs polished off the last remains of his eggs, then settled back with his mug of rum. "Seems that a good number of the crew want more than what they can get with the local wenches. Some of the younger lads are dreaming of bonny young brides, and the older men want good wives to 'go home to' every once and a while. Most want to start families somewhere."

He took a swig from his cup. "Seems you've got more than just your own worries to take care of."

"Bloody hell," Jack huffed as he fell back in his seat. "So I have to find wives for crewmen now? How can I help my crew find women when I can't find my own?"

"You could always look to a matchmaker," Gibbs hesitatingly suggested before taking another drink.

Jack snorted. "Please, Gibbs. If they are so skilled at finding mates for others, why can't they find a husband or wife for themselves?"

The other man nodded in acknowledgement of that fact, and went back to his rum. However, neither man quite put the idea aside.

After leaving Jack to drown his worries in rum, Gibbs headed into the depths of Tortuga on his own. He had a feeling that a very skilled matchmaker could be the answer to not only Jack's problem, but to the bout of loneliness that had lately consumed the crew of the Black Pearl.

As fate would have it, Gibbs had met a man named Joseph Nelson. He was a rather young fellow, and he'd just arrived in Tortuga to open his own medicine shop. He was 'testing the waters,' he said, to see if his business venture would be a success or not. To his surprise, it had.

After being in the pirate haven for less than a month, the lad had already made quite a name for himself, particularly because his headache, nausea and stomach draughts were so effective. There were other brews and herbs he sold, but in a town like Tortuga, anything that could cure a head or stomach ailment was sure to make good business.

In fact, that was how Gibbs had met Joseph. After a questionable, off-tasting meal at a conveniently placed tavern, Gibbs had come down with a stomachache, and had stopped here for help. Joseph himself had concocted a medicine for the problem, and Gibbs had been perfectly fine by lunch the next morning.

Today, however, Gibbs needed something else entirely. He'd heard that Joseph had wed a rather plain girl named Hannah before coming to Tortuga, a girl whom he'd met through the hired skills of a matchmaker. Hopefully, Joseph would be able to provide a little help with the current situation on the Pearl.

Taking a deep breath, Gibbs entered the faintly lit shop.

"Mr. Gibbs!" Joseph greeted him from behind the counter. "Here for another remedy?"

"No, not today," the pirate replied. "I was wondering if you could help me with another kind of…situation."

Joseph looked puzzled, but nodded. "What can I do for you?"

"Well, it's not for me, exactly," Gibbs slowly drawled out. "It's for my Captain and some of my fellow crewmen. They're in sore need of wives, and I figured it was best done through the dealings of a matchmaker."

The shopkeeper laughed and shook his head. "Well, even if that's not my area of expertise, I can at least help you with that."

"You did what?" Jack yelled, angry and horrified.

Gibbs sighed. "It's not such a bad idea, Captain. The matchmaker Joseph went through is Miss Evianna Watkins, and she's from the English town of Port Thomas, here in the Caribbean. That's not more than a few days away from here, so what's the harm?"

What was the harm? Was the man joking? How would it look for Captain Jack Sparrow to hire a matchmaker? His reputation would be in tatters, and no woman would want to be seen with him again! That was the harm.

"This is a nightmare," Jack muttered with a groan.

His first mate sighed again. "Jack, you know that it's time and past for some of the men to find lasses of their own. The older ones aren't getting any younger, and the young ones have thoughts of love in their heads. Let's go and find this matchmaker, if only for their sakes, and you can see if this Miss Watkins is as good as Joseph says she is. Who knows –she might even find a woman for you."

Jack felt himself give way. Thus far, he hadn't found a wife on his own, so why not let someone else do it for him? If she failed, he'd pay her fairly for her time; if she succeeded, Jack would give the woman half of his treasure, and owe her a lot more.

He sighed. "Alright, Gibbs. When the men are finished with their leave, we'll set sail."

AN: Short chapter, but the next one will be longer. Thanks for reading, and please review!