OnlyFans Star Annie Knight and Henry Brayshaw’s Relationship Timeline

Adult content creator Annie Knight and her fiancé, Henry Brayshaw, first crossed paths a decade before their engagement.

The OnlyFans star and Brayshaw initially met working at a pub, building a friendship outside of work. A few years later, the pair tried to date — but Knight noted that it “just wasn’t really the right time.”

“We’ve just grown closer and closer and been best friends the past few years,” she exclusively told Us Weekly in May. “It wasn’t really till the end of last year where we kind of like, ‘Hmm, I wonder if there’s something else here.’ We both were sort of feeling it. But we were like, ‘No, it’s not time yet, I’ve got my job and I’ve got my work.’ We had different goals.”

Fast forward to March 2025 and Brayshaw popped the question to Knight after confessing his feelings for her. The pair are eyeing an October 2026 wedding, with Knight’s dog Billy serving as the ring bearer.

“I’ve got my wedding spreadsheet going,” Knight quipped to Us in August, noting that she and Brayshaw are “not sparing any expense.”

Scroll down to see their love story from the beginning:

March 2025

While Knight and Brayshaw traveled to Cancun with adult content creator Bonnie Blue, he admitted that he was “in love.” One week later, the couple got engaged.

“I’ve known him forever, and we just were so perfect for each other in an unconventional way. A lot of people are like, ‘I don’t understand how this works.’ But we do and that’s what’s important and that’s why it is so perfect, because we understand it,” she told Us in May. “I just immediately knew it was a yes. I’m really excited to marry him.”

May 2025

When Knight slept with 583 men in six hours, Brayshaw supported her from afar.

“He was actually at work the day of the event, but he called me in the morning, wished me luck, said, ‘Make us proud. Have fun. Be safe,’” Knight told Us at the time. “And then called me the night of and was like, ‘How was it?’ And I told him all about it.”

Knight shared that Brayshaw was “just really stoked” that she “went above and beyond” her goal of 200 men showing up to the event.

“He was proud of me for completing it, because I think he was a bit worried that I wouldn’t be able to and that I’d be upset that I couldn’t do it,” she told Us. “He was just really happy for me.”

August 2025

While reflecting on sleeping with 583 men in six hours, Knight told Us in August that the challenge made her feel “closer” to Brayshaw.

“I think it has really made Henry and I just have amazing communication,” Knight explained. “I think we have the best communication of anyone ever in the history of the world. In order for it to work the way that it does, that’s all we need is communication.”

December 2025

Brayshaw showed a glimpse of the messages he receives about his relationship with Knight — and how he handles them — when a user questioned why he would “let [her] do that,” referring to the OnlyFans star’s career.

“She’s saved my life more times than I care to admit,” Brayshaw replied, in part. “I’m her rock — we are an amazing team. We have made a beautiful life for each other and couldn’t be happier. That’s all you chase in life isn’t it? I respect your opinion Ben. Thanks for reaching out.”

To learn more about the serious potential risks and harms of “competitive sex” and other explicit OnlyFans content — read what doctors, mental health professionals and other experts told Us Weekly here.