[Oh...You. How little she knows of her, but Isabela catches the sadness and guilt in her voice and feels a little bad herself hearing it out of her bright and sunny little captain. The girl had asked true, but she hated seeing her past affect the girl in such a way. She smiles then, a small but genuine one as she walks over to ruffle her hair with a little laugh. This night in the past had been rough, but now maybe she can see it for the open door it truly was.]

Come now, no need to look so lost sweet thing. The past is the past, no need to look so sad over things I've put behind me. [...Mostly, considering the bitterness she holds.] You take what you can from it and move on, and I became a fine captain with a good crew after I got out of here.

[But it's almost funny how she mentions the potential of piracy, because she's almost got it right if not the wrong person.]

He was just a wealthy merchant, he wouldn't have lasted a day living the life of a pirate. [A pause as she considers, then figures might as well while they're here.] I did just fine in that position myself for years though.