Kelly Osbourne, the outspoken daughter of rock legend Ozzy Osbourne and TV personality Sharon Osbourne, has lived much of her life in the public eye, including her romantic relationships. From her early days on reality television to her current status as a mother and fiancée, her love life has often been a subject of media interest, marked by high-profile engagements, rockstar romances, and a journey toward finding lasting happiness.
One of Kelly's earliest public relationships was with Bert McCracken, the lead singer of the band The Used. Their romance unfolded during the second season of her family's hit MTV reality show, The Osbournes, in 2002-2003. The relationship, though brief, was a significant part of her early public persona, showcasing the challenges of dating under constant media scrutiny. According to reports, the couple eventually split due to McCracken's reluctance to be in a serious relationship in the public eye.
In 2006, Osbourne was linked to musician Matty Derham of the band Fields. Their relationship gained attention when they reportedly held a wedding ceremony at the Electric Picnic festival in Ireland. However, her representative later clarified that the ceremony was not legally binding, as it did not meet Irish legal requirements for an outdoor venue, leading to much speculation and a strong reaction from her parents.
A more serious engagement followed in 2008 when Kelly began dating model Luke Worrall. The couple became engaged in 2009, a significant step that brought their relationship further into the spotlight. Their engagement lasted for a little over a year before they ultimately separated in 2010. The split was widely reported, with sources citing various reasons, including Worrall's alleged infidelity, which Kelly addressed publicly.
Following her breakup with Worrall, Kelly had a few brief relationships. In early 2011, she reportedly dated musician Rob Damiani, with intentions to keep their romance private as they got to know each other. Later that same year, she was also briefly linked to her longtime friend Anton Lombardi. These periods reflected a time of transition in her personal life as she navigated post-engagement singlehood.
Her next significant relationship was with chef Matthew Mosshart, whom she began dating in 2012. Their connection seemed strong, and they announced their engagement in July 2013. Mosshart had moved from New York to Los Angeles to be with Osbourne, and they often spoke positively about their future together. However, their engagement was called off in January 2014, with reports indicating an amicable split despite the disappointment.
After her engagement to Mosshart ended, Kelly had a series of short-lived romances. In 2014, she was linked to Quincy Brown and later that year, briefly dated model Ricki Hall. These relationships were often the subject of tabloid speculation but did not lead to long-term commitments. In 2016, she also briefly dated film director Kez Glozier for a few months, further indicating a period of exploring different connections.
More recently, in 2020-2021, Kelly dated cinematographer Erik Bragg. Their relationship lasted for approximately a year, and while they eventually broke up, reports suggested they remained on good terms. This relationship was more private compared to some of her earlier high-profile romances, reflecting a potential shift in her approach to public dating.
Kelly's current and most significant relationship is with Slipknot DJ Sid Wilson. Their connection is unique, as they first met in 1999 when Slipknot toured with Ozzfest, the music festival founded by her parents. They maintained a friendship for 23 years before their relationship turned romantic. In January 2022, a source confirmed they were dating after Kelly posted a birthday tribute to Wilson on Instagram. She later shared a heartfelt message on Valentine's Day 2022, stating, "After 23 years of friendship I can't believe where we have ended up! You are my best friend, my soulmate and I am so deeply in love with you Sidney George Wilson."
Their relationship progressed rapidly. In May 2022, Kelly announced on Instagram that she and Wilson were expecting their first child together. Their son, Sidney, was born in November 2022, bringing a new chapter of motherhood into Kelly's life. Sharon Osbourne later revealed the baby's name on a talk show, as Kelly chose to keep details private initially.
The couple's journey reached another milestone on July 5, 2025, when Sid Wilson proposed to Kelly backstage at her father Ozzy Osbourne's final Black Sabbath concert in England. The emotional moment was captured on video, showing Kelly's surprise and joy as she accepted. The engagement solidified their commitment, marking a culmination of their long-standing friendship and blossoming romance. Kelly and Sid have since made public appearances together, including their red carpet debut at the Grammys in February 2024, and have been open about raising their son while Wilson tours, with Kelly stating, "I grew up on the road." Their relationship signifies a period of stability and profound personal happiness for Kelly Osbourne, built on decades of friendship and a shared world of music.