Maybe if I suddenly got a cool idea on her story.
Well if im not mistaken, there is a picture of Madelyn in the MCs house. Maybe just like the Mad Hatter she can guide the MC towards something. A new hat perhaps for him to get for her with his spare money? Or she just messes with him around his house. Placing her hat on the table, moving things around to where they aren't supposed to be? It would be a hell of ton of work, but it's an idea. Counting that your willing of course. Madelyn is one of my favorites too