You've been kind to me too. You're my friend. Whatever you need, if I can help you with something I'd like to.

[He gave her hand a light, affectionate squeeze back.]

Whenever you're ready, that is. Okay?

[He'd let her off the hook after this, he just wanted to be absolutely sure she didn't want to talk about whatever was bothering her. Maybe she just needed some extra encouragement? Either way, the stuff he wanted to talk about wouldn't be an easy subject so this would be the best time to share if she was going to do it.]