[She pauses, trying to put her phrase together carefully. Despite the angst he's feeling now, she can't help feeling envious that he's had so many happy memories with others.]

...I'm sorry. I pray that your memories of those people will help you through this.

[There's another, shorter pause, trying to shake the awkwardness that she feels at the next question.]

...Do you need some company? I have a lot more free time now that I'm no longer a deputy...