her book was only recently published, and that process usually takes almost a year. so likely some time between 2019 or mid 2020 the latest. i think that fits his timeline, right? he could have noticed her doodling in a notebook and watching him a few meetings in a row. then maybe ran into her on purpose before a meeting or getting coffee to ask wtf was up? she’s very protective over her work… i’m sure she spit out a quick lie initially.