Tha's a friend a' yours, right? You gotta tell me 'bout him next time.

[He does want to know more about her after all. Not just her life here but even back home. Back in her Shibuya. His smile persists as she tries to answer him. He can see she's trying too. Neither of them seemed to have much experience with sort of thing, and his way of going about it was, apparently, just throwing out ideas and seeing what sticks.

When she starts to struggle though, he shakes his head, hoping to reassure her.]

Look, yo. I'm aight with whatever ya wanna do. I mean, as long as I'm hangin' out with ya, you know? If you wanna do something you like, I'm down. But I'mma pick the next one after!

[Ah. That last part seemed to come out without him realizing it.]