Hilary Duff and Husband Matthew Koma Enjoy 'Date Night' with Her Ex Joel Madden and Nicole Richie

Hilary Duff and Matthew Koma went out to dinner with Nicole Richie and Joel Madden, as well as Pete Wentz and his girlfriend, Meagan Camper

Nicole Richie, Joel Madden, Hilary Duff
Photo: Josh Abraham/Instagram

Hilary Duff stays friendly with her exes!

The How I Met Your Father star, 34, enjoyed a couple's night out this past weekend with her husband, Matthew Koma, as well as her ex-boyfriend Joel Madden and his wife, Nicole Richie. The group was also joined by Fall Out Boy's Pete Wentz and his girlfriend, Meagan Camper.

Pulse Music Group founder Josh Abraham captured the "date night" in a photo posted to his Instagram Story. In the image, Duff is embraced by Koma, 34, while they stand next to Richie, 40, and Madden, 42.

In a second photo posted to his Story and shared by Entertainment Tonight, Abraham posed with Koma, Madden and Wentz, 42 — all of whom are musicians — and joked in the caption, "New band alert."

Matthew Koma and Hilary Duff, Nicole Richie and Joel Madden
Matt Winkelmeyer/Getty; Stefanie Keenan/Getty

While Duff and Madden have since found love with their respective spouses, the former couple dated over a decade ago. The pair first struck up a romance in 2004, when Duff was 16 years old.

After over two years of dating, the couple called it quits in 2006, and Madden began dating his now-wife Richie.

"Every girl I've ever dated I have respect for, and I always try to leave them on good terms," Madden told PEOPLE at the time of his split from Duff. "I don't see the necessity to be friends with anyone you've dated but definitely out of respect of the time, you have to be kind of respectful and that's what I try to do."

At the time, Duff told PEOPLE that she and her ex-boyfriend remained in touch and had a "great relationship" after ending their partnership.

Hilary Duff, Joel Madden
Marc Andrew Deley/FilmMagic

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The Younger actress later reflected on her years dating Madden during a 2016 appearance on The Love Bomb podcast, describing their relationship as "so all-encompassing" and "so intense."

"It was my life," Duff said on the podcast. "It was like every minute of my day. It was pretty major."

Duff and Koma began dating in 2017 and later wed in 2019. The couple shares two children — Banks, 3, and Mae, 10 months. Duff also has a 9-year-old son, Luca, from her previous marriage to Mike Comrie.

Madden and Richie wed in 2010, four years after they began dating. They share two children: Sparrow, 12, and Harlow, 14.

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