Drake didn't think that taking his wife to the movies to cheer her up would backfire so badly. He had hated seeing her cry yesterday and a movie he wanted to see just came out so he figured they should go like it was a real date. He knew she liked movie theater popcorn.
It seemed to be working somewhat until he saw the last two people on earth he wanted her to run into on a shopping spree. He knew this would happen but why did it have to be here?!
Step one of his plan was making them bankrupt themselves with impulsive spending. Just as they were the most stressed about it, he would implement the next step. Public humiliation. After that, making them lose their minds completely would hardly take any effort at all.
They would be completely useless and incapable of taking care of themselves, getting shut up in some mental hospital somewhere for the rest of their lives. It wasn't jail but it would do.