Which was exactly right. Jack would continue to ask, almost to the point of badgering, until she finally gave in and told him what was wrong. While Jack may keep secrets wrapped around himself as a protective sheet (as securely as he wore his greatcoat), he wanted others to confide in him. Do as I say, not as I do -- that was Jack's motto.
Jack could see the stress painted on her face like makeup. He watched her closely, eyes searching for any little motion or expression that would clue him into what was going on. He knew it had something to do with his future and her past, but what that thing was, Jack couldn't say. Couldn't tell just from her expression.
"Leaving Rhys behind?" Jack guessed, figuring that was as good a guess as any.