Though the problem I'd ask is not quiet related to haskell, I hope talent people here could provide some suggestions. The problem is not just solve the Hangman problem but solve it in sort of AI way. General idea is : 1. Randomly pick words, e.g. 20 from a predefined word list file. ( http://www.word-list.com/) 2. The application play hangman with each word till either WON or FAIL. NO human being interactive. 3. The expect result is the application be able to win the game at most of time before a certain max wrong guess, e.g. 5 Please let me where is a better place to ask such question and thank you so much in advance. -Simon