Acquaintances
Bertie has several friends who keep popping into his life, mostly for Jeeves' help. A list of those who play major roles are:
- Hildebrand "Tuppy" Glossop, who once challenged Bertie to swing across the pool in the Drones club and "looped back the last ring, thus rendering it necessary for me to drop into the deep end in formal evening costume". He is the cousin of Bertie's sometime fiancée, Honoria Glossop, and is usually engaged to Bertie's cousin Angela.
- Augustus "Gussie" Fink-Nottle, who keeps newts and has a face like a fish.
- Oofy Prosser, the Drones Club Millionaire with a pimply face. His wealth apparently exceeds Bertie's, though it can't be by much.
- Richard "Bingo" Little, who had a penchant for falling in love with every girl he met before finally marrying Rosie M. Banks.
- Rev. Harold P. "Stinker" Pinker, Curate of Totleigh-in-the-Wold. Pinker is consistently clumsy except when playing rugby as a prop forward.
- Freddie Widgeon
- Harold Winship, Stands for Parliament as the Conservative candidate in Market Snodsbury.
- Beefy Bingham, Parson in the East End
- Marmaduke "Chuffy" Chuffnel, the young landowner of Chuffnell Regis, an estate he tries to sell.
- George "Sippy" Sipperly, an author who is arrested for assaulting the police on boat race night.
- Claude "Catsmeat" Potter-Pirbright, an old school friend of Bertie's.
- Charles "Biffy" Biffen
- Cyril "Barmy" Fotheringay-Phipps
Bertie is known for being loyal to his friends, willing to do whatever he can to solve their problems, saying "when it comes to helping a pal we Woosters have no thought of self." This has led to problems as he is regularly volunteered for troublesome tasks — he muses in Jeeves in the Offing that "whenever there is dirty work to be undertaken at the crossroads, the cry that goes around my little circle is always 'Let Wooster do it.'"
Bertie belongs to the Drones Club, and many of these characters are fellow members and appear in the separate Wodehouse "Drones Club" series of stories. Bertie is also acquainted with Lord Emsworth, another of Wodehouse's best-known characters, and mentions having visited Blandings Castle.
Bertie also has several adversaries who are constantly suspicious of him and on occasion, threaten him.
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