She was a Maid of Honour to Queen Elizabeth, and took part in the Harefield Entertainment in 1602. In 1602 Sir John Holles tried without success to arrange a marriage for her with Robert Bertie, Lord Willoughby. Willoughby, who was in Siena, was clearly surprised by Holles's approach, and thought he was misinformed about his acquaintaince with Dorothy, who he only knew at court where it was usual "to spend some hours with the ladies" and they had no "extraordinary liking". Holles was acting at the insistence of Dorothy's mother, who urged him to try again six months later when Willoughby returned to London. In 1605 there was a rumour that Willoughy would marry the queen's Maid of Honour, Mary Gargrave, but he married Elizabeth Montagu instead. She described herself as a servant of Anne of Denmark, but was not a member of the household. She,, had travelled to Scotland in 1603 in the hope of finding favour with Anne of Denmark. Her party met the queen ahead of an official group sent to welcome the queen at Berwick upon Tweed. Hastings's party consisted of members of the Harington family, including Anne, Lady Harington, her daughter Lucy Russell, Countess of Bedford, Theodosia Noel, Lady Cecil, with Elizabeth Cecil, Lady Hatton.
Hastings married James Stewart, a Scottish servant in the king's household and a son of Walter Stewart, 1st Lord Blantyre. He died in a duel at Islington on 8 November 1609, fought with Sir George Wharton, who also died. A ballad was printed A lamentable ballat of a Combate lately fought near London between Sir James Stewart and Sir George Wharton, Knights who were both slaine at that time. The dispute started over a game of cards in the Earl of Essex's chamber in Whitehall, A newsletter described Stewart as "a great minion of the king". John Dunbar wrote a Neo-Latin epigam, about the tragedy stressing their equality, published in his .
Begging letters
Sir John Holles, who had become Comptroller of the Household of Prince Henry, recorded in his letter book attempts to secure royal favour and money for Dorothy, and he helped her draft letters to the king, queen, and prince. One letter accompanied an emblem that Anne of Denmark might wear, of an Indian herb that grows although severed from the earth, her mother's milk, so representing her and Stewart's devoted service. In another, Dorothy presumed "in this my cloudy dark misfortune to creep to the warmth of your sacred beams", to the extent that the queen would urge the king to pay Stewart's debts. Her third letter to the queen for money concluded, "I am most loth to be tedious to your majesty, words being a disease which usually accompanies misery". A letter to the king acknowledged a recent gift, and her presumption in begging for the queen's intercession as mediator, asking only for an annuity and £1,300 to clear Stewart's debts which otherwise may traduce the honour of Scotland and his friends. She asked Prince Henry for a place for her husband's servant John Semery. In July 1613 Dorothy Hastings alias Stewart married Robert Dillon, later 2nd Earl of Roscommon, at St Andrew, Holborn. They had a son, Henry Dillon.
