Ross found work as a journalist and critic, but he did not escape scandal. He is believed to have become Oscar Wilde's first male lover in 1886, even before he went to Cambridge. In 1893, a few years before Wilde's imprisonment, Ross had a sexual relationship with a boy of sixteen, the son of friends. The boy confessed to his parents that he had engaged in sexual activity with Ross and also admitted to a sexual encounter with Lord Alfred Douglas while he was a guest at Ross's house. After a good deal of panic and frantic meetings with solicitors, the parents were persuaded not to go to the police, since at that time their son might be seen as equally guilty and face the possibility of going to prison.