he could absolutely have given her a push to steal the cat after having one too many drinks. he'd definitely support her art and maybe displays a few in his shop? haha he'd probably understand a bit about why she'd be uncomfortable about it but would just shrug and say no one is killing cows just for the hide so if he wasn't using leather that part of the animal would just go to waste. he'd be all for swapping stories and making dumb bets back in the day even if he'd say she has an inherent advantage because guys would give up their numbers way faster than girls will hah. he'd also flirt with her a lot i'm sure since jc's ad specifically said " kind of guy that would flirt with his sister (and half the town)" so she sadly won't be immune lmao. i think if they hung out a lot as kids though he might've started flirting with her after he came back from college