Well well well, we're finally getting the boss's true motives.
As it turns out, our smoking mature lady isn't all that mature. She seems like the kind of person who thinks that doing things on your own and not relying on anyone makes you mature, but even the boss knew that she would've most likely went back with her ex when he came back if it wasn't for our dumb MC being...well, dumb. If anything, he knows that she's kind of stuck in between how she wants to live and how she thinks she should live.
Him sending our poor MC to go help her whenever he can is helping her break down her barriers and getting her to open up a bit more, as well as having an honest yet immature guy by her side.