Karen's pirate? Did Kare tell him before that she had a pirate? Jack could only recall vaguely that there was mention of a pirate at some point, but it wasn't on the forefront of his mind. That Jack did, at least, smell good as Karen said. His mannerisms were a bit... off, but he was still clean and relatively attractive for a straighty.
At least Jack assumed that Pirate Jack was straight.
"This City is more than strange, Kare. It makes New York look normal." More than normal. It made New York look almost peaceful on the weirdo front. Unless there were people who ran around dressed like insects in NYC too, but if that was the case, Jack had never seen them. All the better.
"So..." He waved his hands at her, expecting Karen to share her recent happenings. Whatever turn of events had befallen Karen Walker.