 We Really Shouldn't Be Doing This  is a song written by Jim Lauderdale, and recorded by American country music artist George Strait.It was released in September 1998 as the third and final single from his album One Step at a Time. It peaked at number 4 in the United States, and number 2 in Canada.im Lauderdale told Taste of Country that the song came to him when he was living in Nashville. He was living in Buddy and Julie Miller ’s apartment above their house.