In this scene of The Pirates of the Caribbean: Dead Man's Chess, Elizabeth finds Jack boarding up his ship in the lovely port of Tortuga. Elizabeth, who is disguised in men's clothing, sneaks up on him. Jack, realizing that it's her, quickly hides all his alcohol, remembering that last time they drank together, Elizabeth burned all the wonderful rum.
Then of course, he has to hit on her, as she's looking for her fiance.
Pretty Elizabeth vs. Manly Elizabeth...
Well, clearly Jack prefers pretty Elizabeth or inappropriate Elizabeth, and doesn't have a problem with showing it. Of course, he learns better later in the movie when Elizabeth tries to kill him while kissing him.
I don't think anyone in this scene really appreciates how amazing it is to be in Captain Jack Sparrow's presence.