a dilly of a pickle

old-fashioned slang An especially tricky, difficult, or troublesome situation. A pun on "dilly" (a remarkable or extraordinary person or thing), "pickle" (a predicament), and "dill pickle" (literally, a pickled cucumber flavored with dill). This is a dilly of a pickle we're in, Stuart. Just how are we going to explain this to the boss without getting fired? Boy, am I in a dilly of a pickle—I accidentally made plans with two different men tonight! We're in a dilly of a pickle now because the hotel gave our room away!