I second what Fujisan said. Clark's is as good a place as any on that strip of Belmont. I just can't see someone who is that young caring about what the food is like, as long as it is somewhat familiar to them. That's what you'll get at Clark's. Hamburgers and sandwiches will work perfectly.
I think a lot of the suggestions regarding what is "hip" are geared more towards what is hip for a much older demographic. Not to harp on the suggestion, but I think Sushi Samba is about the last place you'd want to take someone that young, and from Springfield. I doubt the poor guy has ever even had sushi. You'd pretty much be buying top of the line fancy food for someone who won't appreciate it.
Lula is also not the best place to bring this guy. He's young and probably eats at Applebee's, so he's not gonna dig chilled peanut satay noodles with gomae and marinated tofu.
~ The username is a long story