This could be pretty interesting, tbh.
I guess they're very similar in role in the game (a bit dodgy, sells you things you probably shouldn't have as a high schooler) and their personalities seem like they would get along well with each other.
It would be really cute, they would probably drop by the other's shops if things were extremely quiet business wise, or on days off just to see each other. I can see them going on relaxing dates to the park or a quiet town.
8/10
(Feel free to comment your own ops, folks)