While taking a recent lie detector test for the magazine's YouTube series, the 34-year-old actress looked back at her "It's Totally Raining Teens" cover with Amanda Bynes, Mary-Kate Olsen, Ashley Olsen, Mandy Moore, Alexis Bledel, Raven Symone, Evan Rachel Wood and Lindsay Lohan in the early aughts.
When asked if the moment was a career high, Duff replied, "Like explain career high? Like personal high or just like a big achievement? Like I remember being like, 'This is cool I was included in this.' But no, this was a very high-stress, anxiety-inducing day. Also, Mandy and I are great friends now. So, this is very funny."
Duff didn't elaborate but fellow cover star Wood has also discussed the shoot. In a series of since-deleted 2014 tweets, the Westworld star recalled, "I was almost in tears after this shoot. They tried that dress on me, I wasn't comfortable but they told me there was no time…cause everyone else took up too much time with their fittings. Then I was given a choice on whether I…wanted to wear flats or heels. I chose flats and was immediately handed heels and told they looked better. Then we were…all lined up, stared at and approved."
She continued, "I was 15 and felt for the first time my identity being erased and the pressure…to shut up and do what you are told. I felt like meat. Since then, I have found my voice. Never again."
Wood also noted that she'd "shot the cover of 'Vanity Fair' since and had a much different experience. It was quite lovely." Wood is no longer on Twitter but her messages were captured in screenshots by the Daily Mail.
The shoot wasn't the only subject Duff covered during her lie detector test. She also spoke about the recent group date she and her husband Matthew Koma went on with her ex Joel Madden and his wife Nicole Richie. The group—which also included Fall Out Boy's Pete Wentz and his girlfriend Meagan Camper—dined at Scratch|Bar & Kitchen in Los Angeles last month.
Though she enjoys her friendship with Madden, Duff said it's not important to her to be close with all her exes. "This is very situational," she said.
But would she ever consider going on a group date with her spouse's ex? "Which one?" she asked Vanity Fair, being told any of them. "With him there? Sure, why not?"
Are you now singing "Why Not?" Same.
Watch the video to see Duff tackle other topics, including whether she misses her Lizzie McGuire wardrobe and if she likes all the music that she's released.
E! News reached out to Vanity Fair and Wood's rep for comment but hasn't heard back.