“You must have left it somewhere,” said Winnie-the-Pooh.
“Somebody must have taken it,” said Eeyore. “How Like Them,” he added, after a long silence.
Pooh felt that he ought to say something helpful about it, but didn’t quite know what. So he decided to do something helpful instead.
“Eeyore,” he said solemnly, “I, Winnie-the-Pooh, will find your tail for you.”
“Thank you, Pooh,” answered Eeyore. “You're a real friend,” said he. “Not like Some,” he said.
Pooh felt that he ought to say something helpful about it, but didn't quite know what. So he decided to do something helpful instead.
Pooh may be "silly" but he's got all the emotional intelligence in the cast of characters.
Sure, being grumpy is part of Eeyore's personality, but Pooh recognizes that he also has an actual problem that he needs help with. He also recognizes that he can't help by just saying things. At no point does he tell Eeyore to cheer up or look on the bright side or anything like that.