Henley waves him off, and while she starts to say something in response, some snarky answer on her lips to continue the banter, it dies as she catches at least a part of that, despite Jack's best efforts. Her expression dims a measure at a time as she tries to find some way of reassuring him, somehow, without beating him over the head with his own embarrassment or upset or whatever that he's never been on a real vacation.

"We're going to have to find you a pair of swim trunks or something," she decides, finally. It's subtle enough, she thinks.