That's a tough question. Let's review the facts. We all know that Christopher Robin is Winnie-the-Pooh's first and best friend. We also know Christopher Robin is not an animal. The first "animal" Winnie-the-Pooh encounters in the book Winnie-the-Pooh (Chapter One) are bees. While bees are really insects, and not really "friends", we'll count them out.



In Chapter Two of the book Winnie-the-Pooh, the first animal friend he sees is Rabbit. (This is the story where he eats too much hunny and gets stuck in Rabbit's hole).



His closet animal friend is considered to be Piglet. Readers do not meet Piglet until Chapter Three, although it's clear Pooh has known Piglet for some time. He has also known Rabbit, Owl and Eeyore for a long time as well.



To complicate matters more, we could take a different approach to answering your question. It has to do with the original stuffed animals given to Christopher Robin Milne. The stuffed bear "Winnie the Pooh" was given to Christopher Robin Milne on August 21, 1921. "Eeyore" was given to Christopher Robin Milne on December 25, 1921. Eeyore was therfore the first stuffed "friend" for a stuffed Pooh to play with. Owl and Rabbit never were stuffed. They were based on real animals. Check out Question 57 for more details on the stuffed animals.



I would go with "Rabbit" as the most "technically correct answer" to your question.