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Yellowauthor said:
I believe he could fall truly head over heels for a woman, but she has to be perfect for him. Not Elizabeth: she's with Will and he never really loved her. Not Angelica: she's much too serious in piratey matters, and is all for getting what she wants for herself. Though he admires that in her, I believe he would instead come to appreciate a woman who would completely devote herself to him rather than herself. Jack needs someone spunky, quirky and eccentric who has a way with words, her own unique personality, and a caring, loving, devoted heart. He would want someone with who he can be his goofy self, and who would be fun and exciting and tolerable when he's in a drunken stupor, but also a good listener for when he wants to tell one of his "tales" of adventure on the seas. A kindhearted, sweet woman, quirky and silly, intelligent, cunning for his benefit (would take his side in arguments against Barbossa, especially in matters concerning ownership of the Pearl), and one who has a rather large vocabulary. I also believe he would find ocean blue eyes attractive, for they would remind him of the sea and thus of his beloved freedom.
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