STOP SHIPPING SIDESHOW BOB WITH A FUCKING KID, AND START SHIPPING HIM WITH ONE OF THESE GUYS INSTEAD (ranked from most obvious to least obvious):
This one's a no-brainer. Krusty's the person Bob wants to kill the most, besides Bart. They give off divorced couple energy. The perfect example of toxic yoai and enemies to lovers.
Mel's basically the non-evil version of Bob. They'd bond over their intrests, and Krusty driving them crazy.
They're both criminals and they were cell mates, but they also contrast eachother nicely. Plus if you yurifi them, they give off massive butch/femme energy.
Homer and Bob are honestly an underrated duo, and I'm a sucker for goofy idiot x smart snob dynamics. I kinda started shipping them to spite the Bob/Bart shippers (I'd much rather see people shipping Bob with Bart's dad).
Okay, this is mostly because Bob and Skinner are two of my favorite Simpsons characters, but they did have some nice interactions in "Day of the Jackanapes". And there is one thing they do have in common; they both don't like Bart Simpson.