Riddling is an interesting genre which is found in every culture and at all periods. They represent one type of wordplay in which the riddler plays upon the sounds of words in order to produce this literary work. The present study is an attempt to investigate riddles in English. It aims at: revealing the most frequent floated maxims by the riddlers in English; finding out the pragmatic aspects that are found in those texts so that the riddlee will be able to comprehend and understand riddles. It is hypothesized that: the maxim of manner is the most frequent floated maxim by the riddlers in the riddles under study and context with its different types (linguistic, situational, cultural and cognitive) are the pragmatic aspects that are found in riddles, and which enable the hearers to understand and comprehend riddles.