Hook and Regina aren't exactly keen confidants, but it's obvious that something is bothering her. And they all need to work together to find a way out of this place, and that means yes, he does care. He just isn't likely to be able to help, considering his luck at being helpful in the hotel.

He frowns at her wording, watching her with a slightly reluctant expression. He wished he could feign ignorance, yet the glimmer of a shadow makes it difficult.

"Stings a bit more when it's personal, doesn't it?" He doesn't need to say who he's seeing to relate.