Hilary Duff surprised fans at her sold-out "The Lucky Me" World Tour stop in New York City on Wednesday when she brought out her ex-boyfriend Joel Madden and his twin brother, Benji, for a performance. The reunion occurred two decades after Duff and Joel Madden ended their relationship.
Duff, 38, changed into a Good Charlotte T-shirt mid-performance at Madison Square Garden before announcing her special guests. "New York, you know I would never come here and not have a surprise for you," she told the cheering audience.
The singer, formerly of Disney Channel fame, then introduced the Madden brothers as "two of my dearest friends." Joel, 47, and Benji, also 47, then joined Duff on stage. The trio performed Good Charlotte's 2002 track "The Anthem," with Benji on guitar. Duff and Joel dated from 2004 to 2006, a period when Duff was 16 and Madden was 25.
Backstage, the former couple posed with their spouses. Duff was photographed with her husband, Matthew Koma, while Joel was with his wife, Nicole Richie. Benji Madden's wife, actress Cameron Diaz, was not pictured.
Duff and Koma, married since 2019, were accompanied by their children Banks, 7, Mae, 5, and Townes, 2, as well as Duff's son Luca, 14, from her previous marriage to Mike Comrie. It is unclear if Joel Madden and Nicole Richie's children, Kate, 18, and Sparrow, 16, were in attendance.
Despite their breakup in 2006, Duff and Joel Madden have maintained an amicable relationship. They have previously attended events together with their respective spouses, including a night out in Los Angeles in 2022. Duff reflected on their past romance in a 2016 podcast appearance, describing it as "so all-encompassing" and "so intense."