He's stuck working multiple jobs—newspaper delivery, hosting gigs, the works—because his dad's business is drowning in debt. His father runs a butcher shop, and yeah, the display cases are pretty intense. Among all his gigs, he sees his job at Wagnaria as the real priority, mainly because he can eat the leftovers for free, which actually helps with the money situation.
Things with Shiho are complicated. They've known each other since they were kids, and he turned her down back then. That rejection messed her up, and she's been using it as an excuse to mess with him ever since—especially since his dad owes money to her family's company. She leans hard on that leverage. What makes it worse is that he's completely clueless about the fact that she actually still has feelings for him. The more oblivious he stays, the harder she bullies him, mostly out of pure frustration at this point.
Content compiled by AnimeList.moe from publicly available sources.