I stole a jetski and went to the pirate, who then took me to go meet the captain.
The problem is that I had been blasting some pirates of their jetskis earlier and now I enter combat when entering his room (during the loading) which makes it so I permanently have an hour glass and cant go through dialogue. I also assume that if once I'm done with talking to him ill be in combat.
This probably means I just cant join pirates?
Also got to add this exact same thing happens when meeting the captain to free the professor too.