Before Jane became Henry's mistress she had engaged in other love affairs at the English court. Her countryman, Louis I d'Orlèans (Duke of Longueville), had been a prisoner ever since the Battle of the Spurs in 1513 - but he still functioned as an ambassador. One of his main tasks was to secure the marriage between Princess Mary and Louis XII in which he succeeded. But the romance with the French Duke seriously damaged Jane's reputation - it has been speculated that she was always in the middle of her twenties and still unmarried. However, the Duke returned to France and Jane stayed behind. With a tarnished reputation, it would seem that Jane was not very popular with the English courtiers. Apparently even the French court had heard of Jane's "adventures". When she was appointed to accompany Princess Mary to France, Louis XII refused to have her serve his new wife - allegedly he thought her behaviour too immoral!
It was at this time that her affair with Henry VIII began. The affair itself was very short-lived but not due to the ever-changing moods of the King (as could be expected). Jane decided to return to France in 1516 and it is likely that she continued her affair with the Duke of Longueville.