It is certain that shortly before Catherine of Aragon ceased to be queen, Jane was attached to Catherine's household in England as lady-in-waiting. She was subsequently placed in the same relations with Catherine's successor, Anne Boleyn (Letters and Papers of Henry VIII, xi. 32). Chapuys, the emperor's ambassador at Henry VIII's court, describes her in 1536 as ‘of middle stature and no great beauty,’ and of pale complexion, a description which her authentic portraits fully justify. But Chapuys, like other observers of the time, commends her intelligence. On 10 Sept. 1535 Henry VIII paid a visit to her father's house, Wolf Hall, and she doubtless helped to entertain him there. From that date he paid her marked attentions, and Queen Anne's miscarriage early in the following year was attributed by the court-gossips to the jealousy excited by the king's treatment of Jane (ib. x. 103). In February 1535–6 it was stated that Henry made her costly presents (ib. x. 201), and Anne's irritation was proportionately increased. In April, while Jane was at Greenwich, Henry sent her a purse full of sovereigns and a letter making dishonourable proposals. Jane returned the letter unopened, together with the purse, discreetly remarking that her honour was her fortune, and that she could only receive money from Henry when she married (ib. x. 245). Meanwhile Anne's enemies found in Henry's avowed attachment to Jane a means of bringing the queen to ruin. Sir Nicholas Carew and others urged Jane in her interviews with Henry to point out to him the invalidity of his marriage with Anne, and to withstand all his dishonourable suggestions unless he was ready to make her his wife. Henry soon agreed to accept her terms. And it was largely owing to his anxiety to set Jane in Anne's place that legal proceedings were taken against the latter on the ground of her adultery and incest. While arrangements for Anne's trial were in progress, Jane, in order to avoid compromising situations, stayed with her brother Edward and his wife in Cromwell's apartments, where the king undertook to see her only in the presence of her friends; and she was subsequently taken to a house belonging to Sir Nicholas Carew, seven miles from London, where she lived in almost regal splendour. Before 15 May—the day of Anne's trial—Jane removed to a house on the Thames within a mile of Whitehall, and there Sir Francis Bryan brought her word of Anne's condemnation a few hours after it was pronounced. Henry himself followed in the afternoon. Four days later Anne was beheaded. As soon as Henry learned the news, he visited Jane, and on the same day Archbishop Cranmer issued a dispensation for the marriage without publication of banns, and in spite of the relationship ‘in the third and third degrees of affinity’ between the parties (ib. x. 384). Early next morning Jane arrived secretly at Hampton Court, and there her betrothal with the king formally took place (Friedmann, Anne Boleyn, ii. 354). The story that the marriage ceremony was performed on the day after Anne Boleyn's execution in a church near the house of Jane's father in Wiltshire, and that a wedding banquet was given in an outbuilding on the estate, is uncorroborated by the evidence of contemporary correspondence (Letters and Papers, x. 411; see drawing of the building in Wilts Archæolog. Mag. xv. 140 sq.) The eight days following the betrothal may, however, have been spent in Wiltshire. The pair arrived in London from Winchester before 29 May, and the marriage was privately celebrated on 30 May in ‘the Queen's Closet at York Place’ (Letters and Papers, x. 413–14). Jane was introduced to the court as queen during the ensuing Whitsuntide festivities. She was well received, and courtiers curried favour with the king by congratulating him on his union to so fair and gentle a lady. Mary of Hungary wrote to Ferdinand, king of the Romans, that she was ‘a good imperialist’ (ib. x. 400), and she showed invariable kindness to the Princess Mary, whom she was successful in reconciling to Henry (cf. Wood, Letters of Illustrious Ladies, ii. 262–3). Miles Coverdale, just before the publication of his Bible, printed the initials of Jane's name at the head of the dedication across the name of Anne, to whom with Henry it was his original intention to inscribe his work. On 8 June Paris Garden was given her. Cromwell described her to Gardiner in July as ‘the most virtuous lady and veriest gentlewoman that liveth’ (Letters and Papers, xi. 17). She paid a visit with the king to the Mercers' Hall (29 June), went with him through Kent in July, was hospitably entertained at the monastery of St. Augustine's, Canterbury, and accompanied her husband on a hunting expedition in August.
Parliament had in July vested the succession to the throne in Jane's issue, to the exclusion of the Princesses Mary and Elizabeth. But it was soon reported that she was not likely to bear children. Her coronation was fixed for Michaelmas, but the ceremony was delayed, and, although her name was introduced by Cranmer's orders into the bidding prayer, rumours went abroad that it would not take place at all unless she became a mother.