In "The Chaperone", Pearl is revealed to be in high school when SpongeBob accompanies her to her prom.
In "Employee of the Month", SpongeBob says he won Employee of the Month 26 times in a row, meaning he has been at the Krusty Krab for at least two years and two months after "Help Wanted" when he was hired.
In "Employee of the Month", the scene where Squidward falls into a hole is a reference to a scene in the PB&J Otter short "Making Cupcakes" where Wanda Raccoon falls into the water while trying to deliver the cupcakes to PB&J. It is also similar to a scene in the short "Test for the Best" where Peanut Otter falls into a trapdoor that Jelly Otter set up.
"The Chaperone" is the first appearance of Pearl Krabs.
In 2021, storyboard artist Sherm Cohen shared a storyboard of the wide panning shot in "The Chaperone" after Spongebob's attempt to "Do the Sponge" lays waste to the prom; there were some notable gags that were removed from this initial version, one of which only partially survived. In the episode, a fish suddenly appears close-up to say something directly to the camera but remains unvoiced. The storyboard features them saying the line, "Has anybody seen my arms?" While the line is absent, the mouth movements match the line, so presumably this was removed late into production.