I’m working on a campaign that has the player meet a creature pretending to be a sphynx and ask riddles of the players.
The trick is that that creature is both not that smart and thinks he’s very clever. They way past him is to praise him for being so smart that he agrees to let the adventurers go
What are some good ‘bad’ riddles to ask ?
The best worst riddle ever written:
“What’s in my pocket?”
Honestly it sounds like the riddles may be clever, but the creature simply thinks the correct answer is wrong. Like “what has four legs in the morning, 2 legs in the afternoon, and 3 at night?” The answer is a person, but maybe the creature says it is another creature that operates literally on this premise. Or it presents the riddle about the head that lies and the head that speaks truth, and has a totally different idea on how the riddle is actually solved, much to the chagrin of your players who are, hopefully, smarter.