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To “dig” someone or something means that you approve or like that person or thing. Saying “I dig you” to someone means they “like” the person. It can also mean “to understand” which was first recorded in 1934.
“Dig.” Online Etymology Dictionary , Douglas Harper, idioms.thefreedictionary.com/dig you. dig you. (n.d.) Farlex Dictionary of Idioms. (2015). Retrieved July 31 2020 from https://idioms.thefreedictionary.com/dig+you