Rumpelstiltskin said: "Nina sings: "Now back in high school when it darkened, You'd hang out in Bennett Park and" Benny: "Usnavi would bring his radio", Nina" As I walked home from Senior Studies, I'd see you rapping with your buddies . . . etc. Either the implication is clear and they were in school together, or Nina at 17 (or thereabouts) walked home from school and saw the others in their mid/later-20's, meaning that Usnavi and Benny regularly hung out in the park mid-day as adults which makes no sense in light of their jobs and Benny's career ambitions.
- Does everyone believe that the source of the conflict between Benny and Nina's dad was clear in the stage version? I've been talking about this with friends for years. Some of us recognized the race issue but others felt that he was reacting to Nina choosing someone whose ambitions were no greater than his own. It was never explicitly stated in the script; I assume that was intentional."
My belief, to the point re: their ages, was Benny and Usnavi were early 20s to Nina's late teens. She was walking home after it 'darkened' so significantly later than the school day ends - probably doing extra studying, extra curriculars, etc. So Usnavi and Benny are hanging out after work (or, for Usnavi, probably on dinner break). At least where I live, "senior studies" could be read as AP courses, which include extra instruction/studying time (often done after school).
I always interpreted Kevin not liking Benny as
- racism, as he makes clear ("not Latino"
- Being protective of his daughter, in a "no one is good enough for my girl" sort of way. He wants the very very best for her, and it's hard for any human to measure up.
- Knowing Benny from a young age. Normally if Nina would bring a boyfriend home, her dad is meeting him for the first time, he's on his best behaviour and delicately throwing out some accomplishments to show he's 'worthy' and get that parental approval. Kevin's known Benny for well over a decade, and in a cut song (Hear me out) it's implied he wasn't the most presentable kid - dressing in what Benny now considers to be not great clothes, breaking open fire hydrants, etc. Kevin has had a front row seat to Benny being human - messing up, making bad calls, falling down. It requires a bit of a knock on the head and laying it out to show him that, yeah, Benny's a great guy.
Benny's plans per 96,000 seem to be quite ambitious. He wants to go to business school and get an MBA (compared to Kevin's own lack of education) and he explicitly wants to be richer than Kevin, and to participate at least somewhat in investing. Unless there's some lines from book scenes I'm not remembering, I don't think it's at all implied that Benny's ambitions are not greater than Kevin's.