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. The nineteenth-century critic George Gilfillan implies that Wyatt and Boleyn were romantically connected. In his verse Wyatt calls his mistress Anna and allegedly alludes to events in her life:
And now I follow the coals that be quent, From Dover to Calais against my mind . . . .
Gilfillan argues that these lines could refer to Anne's trip to France in 1532 immediately prior to her marriage to Henry VIII, and could imply that Wyatt was present, although his name is not included among those who accompanied the royal party to France. Wyatt's sonnet "Whoso List To Hunt" may also allude to Anne's relationship with the King:
Graven in diamonds with letters plain, There is written her fair neck round about, 'Noli me tangere [Do not touch me], Caesar's, I am'.
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. When she attracted King Henry VIII's attentions sometime around 1525, 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.