Has a “ruff” night?

As a detective trying to solve the mystery of the crossword clue ‘Has a “ruff” night?’ , I would start by breaking down the clue into its parts. The word “ruff” is a pun on the rough fur around a dog’s neck, which immediately suggests that the answer might have something to do with dogs. Thinking further, the word “night” adds a sense of time to the clue, which implies an activity that might take place at night.

Putting these thoughts together, I would consider the possibility of a dog sitter or dog walker having a “ruff” night taking care of multiple dogs. This would lead me to the answer “DOGSITS”, a word that perfectly fits the pun and the activity that might take place at night. This thought process shows how focusing on specific word choices and incorporating contextual clues can lead to a satisfying solution to a crossword clue.