wordfile = open('/usr/share/dict/words', 'r') words = wordfile.readlines() wordfile.close() length = int(raw_input("How many letters is it? ")) words = [word.strip() for word in words if len(word.strip()) == length] print str(len(words)) + ' possibilities' firstletter = raw_input("What is the first letter? ") words = [word for word in words if word.upper().startswith(firstletter.upper())] print str(len(words)) + ' possibilities' lastletter = raw_input("What is the last letter? ") words = [word for word in words if word.upper().endswith(lastletter.upper())] print str(len(words)) + ' possibilities' beaten = False for i in range(10): answer = raw_input( 'is the word ' + words[i] + '? ') if answer.lower().strip().startswith("y"): print "You win!" beaten = True break if not beaten: print "HA! Told you I was smart!"