Jack Sparrow first meets Esmeralda Maria Consuela Anna de Sevilla when he is just a boy, the age of nine, living in Shipwreck City. Lady Esmeralda is fifteen, sailing on her grandfather's ship, the Venganza. Originally, her grandfather sent her to a convent school in Barcelona, Spain, but she quickly gets bored of it and dreams to be a pirate like him. Esmeralda: "After my parents died, he decided I must become a fine lady, perhaps serve at court, so he put me in a convent school in Barcelona. I missed him-and the sea-so much." Love for the sea? Sounds like Jack. So grandfather takes her to Shipwreck Cove, in hopes that all the craziness will scare her from being a pirate. That's when Jack first lays his eyes on her, but not the last. You see, her grandfather, Don Rafael, is the pirate lord of the Caribbean Sea so his boat tends to drop by Shipwreck Cove every so often. So Jack, being a mischievous little boy, yanks her braid (not uncommon for children to do to the people they like), and she beats him up! Pretty intense. Jack describes her being "a short, chubby brat". So after that great introduction, they don't meet again for years.
But at the age 20, Jack again in Shipwreck City, as he is in the crew of Captain Teagues ship, the Troubadour. Don Rafael has given in to her becoming a pirate and is in town for a meeting with Teague and some of the other Pirate Lords concerning the rogue pirates. However, after eleven years the meet again. She's still petite for her age, but is no longer chubby, but you can bet she was pretty. Of course, Jack takes a liking to her very quickly. After trying to make himself look the most attractive (doesn't take much), he joins her, Don Rafael, Teague, and some of the other pirate lords for dinner on board Teague's ship. And afterwards he escorts her back to ther grand father's ship. It's not very surprising at all that he charms her pretty quickly. They spend time together while her grandfather and Teague are at meetings. They take food and wine and in a dory to different coves. They swam, fenced, ate, laughed, and talked. Jack says "they talked as though they'd been deaf and mute until they'd met each other." How touching <3 But they keep all this secret, because Teague warned Jack to stay clear of her.
Teague: "Don Rafael's quick with his blade. Even at his age, he'd spit you like a suckling pig, and I wouldn't lift my little finger to stop him." Kinda harsh. But there is another problem in their relationship: Christophe, the secret rogue pirate. Being a very attractive young woman, Jack's not the only pirate with an eye on her. After two weeks of it just being the two of them, Christophe asks to join them. Jack hasn't revealed his true feelings to Esmeralda yet but Christophe showed no such self restraint.
He never misses a chance to hold her hand to help her up, or touch her arm when showing her new fencing moves. It's pretty clear where Christophe is going with this, and Jack's afraid that he'll loose her to this older and apparently more handsome captain. But of course, no one could resist Jack Sparrow, could they? So one early morning she decides to move the dory. But this confuses Jack because she thinks she doesn't want to hang out with him any more. But really, it's just the opposite. Esmeralda: "I . . . I didn't want Christophe coming along." Point for Jack! But it gets better: "He's too forward. And, while the three of us were together, I never got a chance to talk to you. Jack, I've missed you." So they share their first kiss together,while rowing in the about in the dory. Jack always wins!