"The Inferiority Complex of Old Sippy" is a short story by P. G. Wodehouse, and features the young gentleman Bertie Wooster and his valet Jeeves.

[1] In the story, Bertie tries to help his friend, Oliver "Sippy" Sipperley, an editor of a light society magazine who is intimidated by his old school head master into publishing boring essays.

He believes he is spiritually inferior to her because, one year prior, he spent thirty days in jail for punching a policeman on Boat Race night.

Bertie tells Jeeves that Sippy has an inferiority complex and feels subordinate to Waterbury.

However, Bertie comes up with a solution of his own: he will prepare a bag of flour over the door to Sippy's office to fall on Waterbury.

The image of Waterbury covered in flour will embolden Sippy to stand up to him and also confess his feelings to Gwendolen.

Jeeves suggests that it would be better for Sippy to first win Gwendolen's affection by faking an injury and calling out for her, then proposing to her.

To make the story of an accident credible, Jeeves had knocked out Sippy with a golf club.

[3] According to Kristin Thompson, Wodehouse uses cues to suggest offstage manipulations performed by Jeeves that Bertie is not aware of.

Jeeves says he is late because he was dusting Bertie's new vase, but Thompson writes that the reader can infer that Jeeves was actually busy planning Sippy's "accident" with the vase, and adds, "Everything emphasizes this strange five-minute delay, yet there is no reference back to it.

"[4] Similarly, in the story's last scene, it is not explained why Jeeves should have come along with Sippy when he could have waited for Bertie at the flat.

In that way his convoluted explanation could confuse and impress Bertie as much as possible before he revealed the last bit of information–that the vase is broken.