In a dramatic turn of events notable in the world of celebrity relationships, Annie Knight, described as "Australia's most sexually active woman," announced her engagement to Henry Brayshaw on March 24, 2025. The surprise proposal occurred during a romantic dinner in Los Angeles, where Henry, 27, the son of renowned sports commentator James Brayshaw, presented Annie with a stunning diamond engagement ring.
The proposal was as unique as their relationship, with Henry asking the question through a dessert that read, "Will you marry me?" Annie accepted with enthusiasm, showcasing her massive oval-shaped diamond sparkler and captioning the moment with heartfelt messages on social media.
"All bets are off, I’m the winner… I love you," Henry shared on Instagram, publicly declaring his affection for the adult performer. The couple has maintained a relatively private romance, although they have been seen together in various social settings over the years, including Annie’s birthday lunch last December.
However, Henry Brayshaw's past is not without controversy. In 2019, he pleaded guilty to charges related to a violent incident during a New Year’s Eve party, where he was found guilty of assaulting a man while under the influence of drugs, primarily magic mushrooms and cocaine. The incident took place at Jeremy Fox's mansion in Portsea, where Henry harassed guests at the party and subsequently faced significant legal consequences, including a 12-month good behavior bond and a $750 fine.
Henry's lawyer emphasized that he had a previously clean record and had subsequently sought help for a drug addiction, entering rehabilitation shortly after the New Year’s Eve events. Since then, he has focused on his recovery and the pursuit of a more stable life.
On the other hand, Annie Knight's journey has been one marked by ambitious personal challenges and a unique approach to her career. Recently, she expressed her intention to sleep with 1,000 men in 2025, a goal she has promoted across numerous social platforms. In February, she openly sought a boyfriend who could support her unconventional lifestyle, indicating that potential partners must be ‘super secure’ to engage with her world, filled with adult content creation and sexual challenges.
"I want a boyfriend, I'm ready to find love, there I said it," she stated on TikTok, emphasizing her desire for a supportive partner who understands her career choices. Despite her risqué public persona, Annie potrayed herself as kind and generous off camera, stating that her sexual ventures do not define her entire personality.
Throughout 2024, she aimed to surpass her previous year’s record, where she admitted to sleeping with 600 partners. In December of that year, she made headlines by announcing a desire to take 500 virginities over the course of the new year, triggering debates around her lifestyle.
While Annie Knight's goals may seem outrageous to many, she views her escapades as personal challenges and fun endeavors rather than mere publicity stunts. "It's just become a challenge for myself more than anything, and it's just a bit of fun," she remarked in a recent interview.
Annie's bold approach to romance and intimacy has sparked various public reactions, ranging from admiration to disdain. Earlier, she experimented with dating apps such as Hinge, where she received numerous inquiries from men hoping to be her 1,000th partner. This response illustrated the complex dynamics of her public image versus private life, as she attempts to navigate dating amid her controversial career.
However, she stated her intention to maintain some boundaries, noting she would try not to sleep with any of her dates until they had met at least three times. “I shouldn’t have said that on the internet because they’ll stick through to the third date and probably leave me,” she joked, highlighting her sense of humor despite the intense scrutiny that follows her.
In the midst of her pursuing love, Knight remains undeterred by her reputation and is eager to balance her personal aspirations with her public persona. Her relationship with Henry Brayshaw, though steeped in notoriety, is transforming as she prepares to embrace a new chapter in her life.
The couple's decision to share their engagement on social media reflects not just their connection, but also an evolving narrative that intertwines love with the complexities of modern relationships influenced by past actions and reputations. Animated by the vibrant world of OnlyFans and the ever-watchful eye of journalism, Knight and Brayshaw are determined to carve their own path.
As they turn this page in their lives, both Annie Knight and Henry Brayshaw continue to challenge societal norms while sharing their journey with their followers. While their union faces scrutiny and speculation, their commitment to one another stands at the forefront as they step into this new phase together.
