ok wait there's gold in here... i actually really like the idea of syo being a hateful troll that he just can't seem to shake regardless of platform, to the point that he knows her handle just at a glance...

playing on a couple things you mentioned, what if they dated in like......... middle school after she asked him to go out with her, and it was kinda cute actually—but they broke up messily (loudly, in the school hallway) triggered by him offhandedly implying her poetry she keeps giving him sucks

now working in the coffee shop he just kind of lets her have her little space to write because he still feels kind of bad about what he said all these years later, but it doesn't stop him from acting annoyed about it.