On the cute side, they could just have a convo getting to know one another better, with Somber not being able to say much because he doesn't remember anything about himself especially that early on. I don't think he realized he could sing until he was helping Alfira out with her lyrics. So there'd be hints of things like that, like he clearly has a thing for music so they can chat more about that. He had a flute with him most of the time, so maybe he can learn that he can play the lute too by playing hers?

Dude is an open book with pages written in invisible ink. I always had this idea that his "companion quest" would involve him finding music sheets and playing them, and having some memories (good and bad) associated with the song.

On the very much less cute side, I am all for writing out the uhhh evening session, chase sequence and all. 8) It can take place the same night as whenever the cute convo happened. I'm very much open to anything. I'm happy that you've reached out!