debuted in 2003 as a commercially successful film despite low expectations. The adventurous and exciting swashbuckling plot combined with eccentric characters vastly contributed to the franchise’s victory at the box office. One of its major ensemble characters is the antihero, Jack Sparrow.

While ’s unconventional personality is the main attraction, fans could also notice how he does not fit the Prince Charming category. Throughout the movies, he has been romancing different female characters who ended up becoming his old flame or newfound enemy. There might have been more, but here’s a list of the captain’s known love interests:

Giselle And Scarlett

These were the two ladies that Jack Sparrow met in Tortuga who both ended up having an affair with him. Jack proposed to Giselle by giving her a ring with red gemstone, and upon realizing that the man was serious about his proposal, she immediately dressed up for their wedding.

As she went to the dressing room, she saw Scarlett with the same ring. Furious and dumbfounded, and realizing that they were two-timed, both of them confronted Jack. The pirate received a resounding slap in the face.

Anamaria

Although Zoe Saldana did not make any recurring appearance after this, she made certain that it is something Jack Sparrow will never forget. Anamaria greeted Jack with a hard smack on the face, suggesting that they had a not-so-good history.

Anamaria was a great sailor, and her attempting to join aboard the Motley crew in the Interceptor was to remind Jack of what he stole and never returned. To pacify the enraged woman, he promised to give her the Interceptor as a replacement for the stolen boat.

Elizabeth Swann

It was clear from the beginning that Elizabeth Swann and Jack Sparrow have this strange chemistry. She tried to lure him into thinking that she fancies the pirate, which turned out to be just a part of her cunning plan.

Their relationship is indeed platonic (more like chaotic) even after she let him kiss her. After all the adventures that they have been through, both of them are still willing to sacrifice one another to save themselves. A classic example would be Elizabeth cuffing Jack Sparrow to the ship as a sacrifice to the Kraken.

Tia Dalma

Tia Dalma, or Calypso, is the sea goddess that sailors both loved and feared. It was implied that she and Jack Sparrow shared a romantic history due to her willingness to help out seafarers.

Although they did not totally brush through their short-lived past, Tia Dalma and Jack have no plans of rekindling their long-extinguished lovers’ flame. She, however, still show quite the amicable affection by accepting favors from the rogue pirate.

Angelica

Despite all the aforementioned characters being Jack’s old flames, Angelica is the only one that particularly received the status of a true love interest. The daughter of Blackbeard was introduced in as a relentless pirate. Her only one goal in life is to save her father’s soul from eternal damnation.

She mastered the art of the con from when she and Jack engaged in both love and piracy affairs. While together, they both lie or double-cross each other. What a fascinating couple they were!