Boswell met O'Grady at Dessau on September 25, 1764, noting that

"[a]t supper this night he talked a vast deal of bawdy concerning a Mademoiselle Stenix, who sat near me. I looked grave and seemed to give no attention to his discourse, by way of reproving him. At last, he said that "she would go like a pair of lobster's claws". This ludicrous idea struck me so much that I burst out into a fit of laughter, and Master O'Grady was heartily pleased."

Boswell met O'Grady a few days after having left Dessau, on October 4, 1764, in Leipzig, where O'Grady was to sell some [horses] of his own having apparently freighted a ship from Ireland. On that same day, Boswell noted O'Grady's great facility for speaking and swearing in German. They dined together with Neitschütz on October 5.