In 1895, Lewis Carroll, the author of the iconic novel Alice in Wonderland and a renowned logician, composed a collection of mathematical problems while he was suffering from sleeplessness. However, Carroll seemed to have overlooked a crucial paradoxical error in his presentation of one of these problems, which is analysed in this book, along with questions such as: Do men have more sisters than women? Why do people find their own coincidences more surprising than those encountered by others? How are life and death expectancies treated probabilistically? Statistics, probability, coincidences, randomness and infinity are explored in this book – a collection of essays written over years of research – through a variety of everyday anecdotes and situations, aimed at students, teachers and readers interested in enriching their knowledge of these subjects.