Mary Boleyn is often remembered as “the other Boleyn girl” – the sister overshadowed by Anne’s dramatic rise and fall. However, she had her own connection to Henry VIII, one that remains incredibly unclear. Unlike Anne, Mary never became queen, nor did she hold significant influence over the king. But what do we actually know about her relationship with Henry, and how much of her story is speculation?

When Did Their Affair Begin?

The exact timeline of Mary Boleyn’s affair with Henry VIII is uncertain. Historians estimate it likely took place between 1519 and 1522, while Mary was married to courtier William Carey. Some believe their relationship may have started when she served as a maid of honour to Queen Katherine of Aragon, possibly even during Henry’s diplomatic visit to France in 1519.

However, there is no surviving evidence to confirm when the affair began or ended. The first real acknowledgment of it came later, in the 1520s, when Henry sought to annul his marriage to Katherine and marry Anne. His past relationship with Mary became a political issue, as the church argued that having been with one sister made it improper to wed the other.

How Serious Was It?

Unlike some of Henry’s mistresses, Mary Boleyn does not appear to have gained much from her relationship with the king. There is no record of Henry bestowing her with titles, land, or significant wealth – something he did for other women in his life. This has led many historians to believe that the affair was brief and relatively unimportant to him.

Still, Mary’s lack of political ambition may have played a role in her quiet exit from Henry’s life. Some suggest she was never interested in leveraging the affair for personal gain, while others argue she was simply dismissed once Henry’s attention moved elsewhere.

Were Mary’s Children Fathered By Henry?

One of the most debated aspects of Mary’s affair with Henry is whether he fathered her children. Mary had two known surviving children:

• Catherine Carey (born c. 1524)
• Henry Carey (born c. 1526)

Henry VIII never publicly acknowledged the children, unlike his known illegitimate son, Henry FitzRoy. Some argue that Henry’s refusal to recognise the Careys as his own children suggests they were not his, while others believe it was a matter of discretion, especially given his later pursuit of Anne.

The Impact on Anne Boleyn

Mary’s past with Henry became an obstacle when the king sought to marry Anne. Henry had to send for a dispensation to get permission to bypass the biblical prohibition against marrying one’s brother’s wife – a rule Henry himself had previously invoked to justify divorcing Katherine of Aragon.

Did this cause tension between the Boleyn sisters? It’s impossible to say for sure, but there’s little evidence that Mary and Anne were particularly close. While Anne climbed to power, Mary remained in the background, and after marrying a commoner, she was banished from court altogether. You can read more about Mary and Anne’s relationship here.

Final Thoughts

Mary Boleyn’s affair with Henry VIII remains one of the more elusive Tudor scandals. While history remembers Anne as the sister who changed England’s fate, Mary’s own story is filled with unanswered questions. Was she merely a passing fling for the king, or did their relationship hold more significance than we’ll ever know?

What do you think? Could Mary’s children have been Henry’s, or was she just another brief courtly romance? Let me know in the comments!