Many legends and conjectures have grown up around the notion that the young, unhappily married Wyatt fell in love with the young Anne Boleyn in the early-to-mid 1520s. Their acquaintance is certain, but whether or not the two shared a romantic relationship remains unknown. Nineteenth-century critic Rev. George Gilfillan implies that Wyatt and Boleyn were romantically connected. To quote a modern historian "that they did look into each others eyes, and felt that to each other they were all too lovely.." is a quite possible scenario. In his poetry, Thomas calls his mistress Anna, and often embeds pieces of information that correspond with her life into his poetry.
"And now I follow the coals that be quent, From Dover to Calais against my mind..." These lines could refer to Anne's trip to France in 1532 right before her marriage to Henry VIII. This could imply that Thomas followed her to France to try and persuade her otherwise or merely to be with her. Later in his life, Thomas writes, while referring to a woman, "Graven in diamonds with letters plain, There is written her fair neck round about, Noli me tangere, Caesar's, I am;"
This shows Wyatt's obvious attraction to a royal lady. According to his grandson George Wyatt, who wrote a biography of Anne Boleyn many years after her death, the moment Thomas Wyatt had seen "this new beauty" on her return from France in winter 1522 he had fallen in love with her. However, soon after Anne's arrival in England, she was in a relationship with Henry Percy. When she attracted King Henry VIII's attentions sometime around 1524, Wyatt was the last of Anne's other suitors to be ousted by the king. According to Wyatt's grandson, after an argument over her during a game of bowls with the King, Wyatt was sent on, or himself requested, a diplomatic mission to Italy.