Chapter 14 shows how she fights (to MC it was a brain damaging spectacle), chapter 15 has MC tell that she's always sought to get things she thinks would be good, as well as her having no sense of value when it comes to exchanging items (with her always oferring too much compared to what she'd get).
Those points, and her being a hardcore tsundere (and having her own negative opinions about him), were probably why she and OG Shen Shi broke up (since our MC indeed didn't meet with her prior to the froggy event, unless there was a significant time skip at any point?). Neither side saw the relationship working.
To me the biggest point of confusion would be how disguised Shen Shi's telling off reminded her of her ex-boyfriend.
Was there a big time skip, or is this story going with MC having his memories repressed up until a point, but his old life's personality leaking through prior to him 'waking up' as the story's author? Or is it the world course correcting (since that story's MC was supposed to be a dude, but he got a chick instead)?
I feel that had there been a novel of this story in active translation, it'd help clarify things.