It is often tricky when you are asked to estimate some odd quantity, like how many people dressed in panda suits there were at a party. The person asking you to guess is usually hoping to surprise you with the large deviation of your guess ("what you'd expect") and the actual quantity. But you, the guesser, can't help but take into account the fact that they are asking you, which they presumably wouldn't be doing unless the quantity to be guessed were extremely unlikely and otherwise surprising.
So, the supposedly naive guesser is forced to either guess especially high and annoy the asker, or guess low and appease the asker. Guessing high makes you look like a smartass, while guessing low is tedious.
As a young lad, I would never really know how to choose between guessing high and low, and the choice often brought on some anxiety. But now I usually just explain the whole situation, indicating how being asked to guess has instantaneously shifted my probability distribution. Incidentally, I no longer have any friends.
(Inspired by a representative convo with Brittany)