Shit, you don't even have to go that far back. Look at that weird discord slime roleplay game thing he played in. Didn't he start having a panic attack doing shit like trying to run non-existent commands like "goddess revival" or something?
I can't even imagine him playing Chess. There's nothing there for him to grab on to. No characters, no lore, nothing to self-insert with. It's a game of logic and strategy in it's purest form without distraction or fluff. Chris wouldn't understand anything about it, and he hates not understanding things, only second to being labeled a social outcast. It's where his magical thinking comes from, he doesn't need to learn anything about science if he just assumes the world works with magic.
Of course I'm probably reading way too far into this and it's equally as likely that he was just bored and wanted to try Chess because he's a pseudo-intellectual and maybe he didn't have a tantrum because he was taking his meds and/or that dude let him win a few rounds first as to not scare him off.