To dream of someone telling you riddles is symbolic of mysteries, Ps. 49:4 Related DreamsRiddle To dream about a riddle, or trying to solve a riddle, signifies that your patience will be tested in some situation or challenge you have chosen to undertake. You can also expect that this task will tie up some of your finances.Riddle 1. Feelings of inadequacy in facing problems, dealing with life. 2. A project will require more careful analysis than originally thought. 3. More obstacles than originally imagined.