I assume that it is due to the writers not wanting any of the characters to have NEW long-term relationships, the only exception being Patty who has been with someone for a while now and even have a child.
It isn't just Bart, it has happened to Ned, Lisa, Nelson, Edna and Skinner, Comic Book Guy, Agnes and even Ralph haha, I guess the show doesn't want to create relationships but instead focuses on the whole adventure of dating and turning it into ideas for episodes. This is my theory LOL hope it helps hahaha :)
posted over a year ago
thanks, that's actually a pretty good theory lol ;)