Disclaimer – Disney owns the entire franchise of Pirates of the Caribbean.

Wee Jackie's first crush, and rejection.

First Valentine

Jack Sparrow could not help but grin when he saw that look on the face of the hapless young man as he gazed upon the lovely form of Elizabeth Swann. No doubt the young man felt well out of his depth given the humble bearing he had. Most likely he was a mere apprentice or servant, with no hope of paying court to the lady, who happened to be paired with the new commodore, so he heard. Poor pup. Jack Sparrow should know he had been there once.

"Methinks the laddie is in lurve…" Granny Grace nudged her captain. Edward Teague took a gulp of his rum and glanced across to where his young son was perched on a barrel. Jack Sparrow was staring across the floor of only tavern on Shipwreck. He was looking at a golden-haired girl perched on a bar stool beside another pirate captain. No, not just any other pirate captain but "Goldie" Marquis Rocheforte. The man was a legendary privateer in his youth, a noble of French blood before he turned his back on his king for the lure of piracy. Rocheforte was also the meanest pirate on this side of the Atlantic, even Granny Grace was not going to stick her neck out that far should he take offence to the ten-year-old cabin boy drooling at his precious princess.

The oblivious princess was about Jackie boy's age, with the spun gold hair of her father's. She was dressed in a lacy shirt of finest silk and silver-studded velvet breeches match her father's garments. Her name was Celeste-marie. They had heard the father call out to her earlier. She was a sweet-faced angel with a cupid-bow mouth and her golden tresses tied back with a single velvet bow. No wonder poor Jackie was smitten. The boy shyly ventured forward towards the father and daughter. The girl laughed at some joke her father made. Jackie thought it was pure music, enough to rival the songs of the angels themselves.

Someone called out to Captain Rocheforte. Dropping a kiss on his daughter's curly head, he left the bar to attend to some business outside. No one was suicidal enough to harm the man's daughter when he's within screaming distance. The little princess was perfectly safe and could not be safer had she been cloistered in a fort guarded by a battalion. Mustering up his courage, Jackie haltingly greeted Celeste-marie.

"H-hi…" he gave a weak smile.

"Bon jour…" the girl replied with a radiant smile.

Granny Grace and Captain Teague watched on with growing interest as their young cabin boy made his first clumsy attempt at picking up a girl.

"Rum?" Jack enquired and offered her his own tankard, which he had yet to touch.

"Merci," with a smile, she took the tankard from his hand and took the daintiest of sips. He thought that in that instant, her innocent baby-blue eyes took on a contemptuous cast. It made him shudder involuntarily.

That was all Jack understood before someone seized him by the back of his shirt and hurled him bodily out of the nearest window into a muddy pig sty.

"Stay away from Celeste-marie, dirty rat," the words were delivered in a deathly quiet tone. Captain Rocheforte had returned.

Jack staggered up from the mud. He could make out the pair leaving the tavern. Rocheforte storming out while his girl trotted at his side. She did not even spare her unfortunate suitor a glance. Jack understood even more when he saw her run towards an older boy, throw her arms about his neck and shower him with kisses and terms of endearment under her father's watchful eye. Clearly approving of this particular suitor, the French pirate smiled and gave the youth a warm hug. The trio then strolled off in the direction of their ship.

"Let me kill that fop!" Teague hissed as his cook held him back.

"Not worth yer time, Eddie," Grace shook her head.

"No one throws my Jackie boy outta a window!"

"Boy's gotta learn," Granny Grace replied. "First lessin in dealing with lassies. Trust em not."

"I'm fine, da…" Jackie sniffed and blinked away his tears. He wiped some blood off his brow where he had hit a rock in the sty. Some curious piglets were nuzzling his bare feet and it tickled. He ploughed his way through the sludge and over to his granny and da. "Guess she's outta me depth, eh?" Jack tried to smile but it hurt too much.

"Come on, Jackie boy. Lemme git ye some rum," Teague shrugged.

Jack Sparrow was tough. He would get over it. In fact, the golden-haired angel was soon replaced in his affections by a saucy barmaid in Aruba. Then later a feisty senorita in Spanish convent… Celeste-marie? Rumour had it she went down with her papa's ship when they ran into a British man-of-war outside Portsmouth.

Jack Sparrow watched on as Elizabeth Swann glanced at the young apprentice. That look was free of any contempt. It was almost overflowing with tenderness. Sensing her eyes on him, Will Turner blushed and hastily glanced away. Go for it, whelp. I'll be rooting for you. Jack Sparrow silently toasted the young couple.

Author's Notes:

Things did not work out well for Jackie boy, did they? Actually, it is so much more fun to have our favourite captain single and available.