[The question is harder to answer than it sounds, at least for Ezra. He's only known Obi-Wan for a few weeks. That's not much time to figure out what might cheer someone up. Still, Ezra's had time to give this some thought.]

He needs something that will make him stop thinking about whatever he's worried about. [That part's said with a firm nod.] So it can't just be something to make him smile. It's gotta be something to keep him thinking about something else.

Does he like going on missions? You were his master. Maybe going on a mission with you would help.