OH I HAD AN IDEA suddenly and randomly and since I read around on the CR meme and saw the whole ~regular teenager~ thing on your plot point list.

Bart is basically the perfect person to drag people into situations they really don't actually want to be in but just say yes to get him to finally shut up. (see: every episode of season 2 Bart's in) And then they normally end up enjoying themselves. It's either a curse or a special superpower.

Also they can bond over coming from horrible realities somewhere down the line.