The How I Met Your Father star sat down with Andy Cohen on Bravo’s Watch What Happens Live this week, where she was asked by a viewer about a February 2022 photo which featured herself, husband Matthew Koma, Richie and Richie’s spouse, Good Charlotte frontman Joel Madden. Duff dated Madden from 2004 to 2006, before he and Richie tied the knot in 2010.
While Duff acknowledged that the "date night" pic (which also included Fall Out Boy’s Pete Wentz and his longtime girlfriend Meagan Camper, as well as music executive Josh Abraham and his partner Gina Abraham) had surprised many fans, it wasn’t weird at all for the Lizzie McGuire alum to spend time with her former boyfriend. The mom of three told Cohen that she has a “good relationship with their whole family.”
“We’re neighbors and we actually hang out all the time,” Duff explained. “I was just in her driveway honking for [Nicole] to come drink wine with us the other day."
Unfortunately, Duff said Richie wasn’t available, as The Simple Life alum was in “bed by eight.”
Duff recently reflected on changing friendships in a March 2022 interview with Vanity Fair, in which she recalled her participation in the infamous teen-centric 2003 cover of their magazine, titled “It’s Totally Raining Teens.” In addition to Duff, Mandy Moore, Amanda Bynes, Mary-Kate and Ashley Olsen, Alexis Bledel, Evan Rachel Wood, Raven-Symoné and Lindsay Lohan appeared as the featured faces within the youth-focused issue.
“I remember being like, 'This is cool I was included in this,' but no, this was a very high stress, anxiety-inducing day,” the Material Girls star told Vanity Fair. "Also, Mandy [Moore] and I are great friends now, so this is very funny.”
Last year, Duff also revisited her romantic past — albeit for a heartbreaking reason. Following the death of Aaron Carter in November 2022, the “So Yesterday” singer penned an emotional note on Instagram, writing, "I'm deeply sorry that life was so hard for you and that life was so hard for you and that you had to struggle in front of the whole world. You had a charm that was absolutely effervescent ... boy did my teenage self love you deeply."