Hilary Duff Performed With Her Ex-Boyfriend Joel Madden On Tour

Hilary Duff is currently on the road for the first time in nearly two decades on her whirlwind Lucky Me Tour, but at Madison Square Garden, her fans were the lucky ones. On Aug. 5, during her first of two nights at the iconic New York City arena, the singer brought out none other than Good Charlotte, aka her ex-boyfriend Joel Madden and his brother Benji.

After performing her reflective new track “Adult Size Medium,” Duff seemed like she was about to go into her hit “Come Clean,” but then swerved. “New York, you know I would never come here and not have a surprise for you,” she said to the crowd, as seen in footage posted on her Instagram fan account. “Can you please give the warmest welcome to my friends Good Charlotte?”

Together, the brothers and Duff’s band kicked into their 2002 hit “The Anthem,” with Duff taking over the second verse in a very unexpected moment of nostalgia.

While the appearance was a shock to fans, she actually teased her surprise guests with her outfit. Every night on tour, Duff has been wearing an oversized vintage T-shirt featuring a different artist, ranging from Britney Spears to Hannah Montana. Naturally, on Aug. 5, she repped Good Charlotte, which was clearly more than just a nod to her ex-boyfriend and now-close friend.

Duff and Joel were an item for over two years, dating from 2004 to 2006. During that time, their relationship also became professional, with the two and Benji collaborating on Duff’s 2005 singles “Wake Up” and “Beat Of My Heart,” both of which happened to earn spots on her 2026 tour setlist.

Since their relationship ended, Duff has stayed friendly with Joel, and their families have become close. In fact, Joel’s wife Nicole Richie was even in attendance at the show, posing backstage with the brothers, Duff and her husband Matthew Koma, as seen on Benji’s Instagram Story.

“I have a good relationship with their whole family," Duff said on Watch What Happens Live with Andy Cohen in January 2023. “People are like, ‘What?’ We’re neighbors. We actually hang out all the time. I was just in their driveway honking for [Nicole] to come drink wine with us the other day. I think the whole world's mind was blown for a second. It’s lovely.”