It is extremely difficult to write games with flirtation interaction that involves the player.
The tonal shift from 'Player's character doesn't want to be at work' into a 'Player's character is vulnerable to be flirted with' came across a little disjointed.
Without the setup of character building, it feels like the player is meant to personally be won over with how the text is written rather than putting ourselves into the shoes of Kate and how she sees the world.
As a suggestion, it might be possible to lay out a little groundwork on the life of this Player Character (Kate) beforehand. Perhaps having us play through a few bar shifts? Understanding what it's like to be in the role, revealing bits of exposition, setting up plot hooks for Kate to have curiosity about the intimate nature of people; the player is then aware of the intended premise when the main antagonist arrives.
Final note: At the 'always playing it safe' dialogue, I really wanted to yell at the computer about how it's a choice based on defining ourselves in a chaotic world. Even the overly simplified good person / bad person narrative for how the world is, is part of this choice of defining self. heh. Ah well.
Thanks for making this game :)