Hannah & Jake - Part way through the night.
"Liberating." He said with a small chuckle. "I'll admit I was floundering there for a bit, but things seemed to have worked out a bit. How is it being free?" Jake asked, knowing her situation was a bit forced. "I mean beyond the obvious." He nodded to the club as he took a drink.
Making connections with those who had been on the island was a sub part of his assignment, so long as it didn't jeopardize the larger picture. So, finding out what she'd been up to, while a completely normal thing to ask, was also him filing away info for a report later.