Harboring hard feelings about her exes is so yesterday for Hilary Duff.

Still, remaining friends 20 years after a romantic relationship ended isn't for everybody, but it has worked out for her and Joel Madden. So much so, he and brother Benji Madden showed up for a surprise performance of their tune "The Anthem" during Duff's Lucky Me Tour stop Aug. 5 at Madison Square Garden.

"I brought two of my dearest friends to New York City tonight," she told the crowd in announcing the Good Charlotte rockers. "Talk about some day oners."

In fact, they go all the way back to the '00s, the now-38-year-old Lizzie Maguire alum having dated Madden when she was a teenager. But even though their young love fizzled in 2006—and Madden coupled up with his eventual wife Nicole Richie that same year—Duff insisted at the time there was no big drama behind the scenes.

"There was nothing, no fight, no, ‘He did this, I did that,'" she told Ryan Seacrest on his radio show in February 2007. "It was just time for people to move on and do different things."

In fact, she continued, “I had a really great relationship with him, and we still have a great relationship, which is really good and unusual. He’s a good person, and I always will care about him.”

Declaring herself ready to "like a guy," Duff, then 19, continued, “Dating is fun. I kind of feel like a guy! It’s, like, I can do it now. But I feel kind of wrong at the same time. I’ve never gotten to date before, so it’s kind of exciting. I’ve always just had a boyfriend, you know? I’m young!”

She later admitted, however, that falling for Madden when she was 16 had been "all-encompassing."

"It was so intense," Duff—then newly divorced from first husband Mike Comrie after six years of marriage—recalled in 2016 on Younger costar Nico Tortorella's The Love Bomb Podcast. "It was my life. It was like every minute of my day. It was pretty major."

More major? Meeting Matthew Koma. She and the musician have now been married since 2019 and share daughters Banks, 7, and Mae, 5, and son Townes, 2, plus she's mom to son Luca, 14, with Comrie.

Somewhere along the way, their family moved into the same neighborhood as Madden and Richie, who share daughter Harlow Kate, 18, and son Sparrow, 16, and now...

They're enjoying "family night at MSG," as Benji captioned an Instagram Story photo of himself with his brother, Richie, Duff and Koma after the show.

But it came as a pleasant surprise when it was revealed in 2022 that Duff and Madden did, in fact, socialize.

"I think the whole world's mind was blown for a second," Duff said on Watch What Happens Live with Andy Cohen in January 2023 of the reaction to the photographic proof that she and Koma were on a group date with Madden, Richie and other couples. But, she added, "I have a good relationship with their whole family. People are like, 'What?' We're neighbors. We actually hang out all the time."

Yet while it was "lovely" to have them in her life, she had admitted to Vanity Fair the previous year that her friendship with Madden was "very situational," as she didn't feel the need to stay in touch with all of her exes.

Of course, it also wouldn't work if Koma and Richie weren't on board with this arrangement, but they all get along famously.

When Koma paid Instagram tribute to his friendship with Madden for the "Boys & Girls" singer's birthday in 2023, he proved the comfort level was high by including a throwback pic of Madden and Duff, captioned, "It's not even that weird that you dated my wife...It just makes me feel closer to you."

And when Koma and Duff spent Halloween the following year with Richie and Madden, they came dressed for the occasion—as the Madden brothers. 

Still, theories abounded in November that Duff's 2025 song "Mature"—described by the singer as "a little conversation that my present self is having with my younger self"—was a nod to Madden, 47, who was in his 20s when they dated. Seemingly in an effort to quiet the noise, Richie posted a photo of herself hanging out with Duff, captioned, "'Mature' is not the word I would use to describe us, but regardless, this song is a BOP."

The House of Harlow founder has since shared how much Duff meant to her even before fate brought them together.

“Hilary Duff has been my friend for about seven years,” Richie wrote for TIME in April when Duff was named one of the publication's 100 Most Influential People of 2026, “but in the minds of millennials everywhere, she’s been our friend for most of our lives.”

The 44-year-old continued, "She is the girl we danced with in our bedrooms then and the woman we all want to have dinner with now...Somehow mothering four children, leading a massive pop resurgence, and still making time for a fun night with her girlfriends for a glass of wine (or seven)."

That's another plus to living within walking distance.

And now it's time to raise a glass to more celebrity exes who stayed friends:

No, they are never, ever, ever getting back together. But at this point—between the birthday parties, the friendly embraces and even freaking acting out a sexual fantasy in a star-studded virtual reading of Fast Times at Ridgemont High—it feels like the former Hollywood golden couple is just taunting us. 

You know you're cool when you can pop into your ex's talk show and give him a hard time. Such was the case when Sarah turned up on Jimmy's stage to chat about her new show, I Love You, America and his "cute," "bright," "funny" wife Molly Kimmel. "It's not fair!" she cracked. "She gets, like, new woke Jimmy. I had Man Show Jimmy."

TBH, we might still be mourning this relationship harder than either of its participants. Because when Anna—now married to cinematographer Michael Barrett—heard that Pratt was set to wed Katherine Schwarzenegger in 2019, she offered to officiate. She even sent over a gift after the newlyweds welcomed daughter Lyla in August 2020. Thrilled for son Jack to become a big brother, a source told E! News at the time that Anna "is very supportive." 

It would have been super easy for the exes' relationship to become a flop. But more than four years after a messy split, the HGTV stars are still killing it at two projects: parenting kids Taylor and Brayden and turning run-down properties into someone else's dream home.

Literally "best friends" as the rocker put it in a 2013 interview with Oprah Winfrey, the parents to actress Zoe Kravitz still consider themselves kin. "We're one big happy family," Lenny said of his ex, who went on to wed Jason Momoa before their 2020 split. "It's beautiful, and it just shows you what can be done."

After the Dancing With the Stars co-host and former hockey player called in quits in 2020, the pair have continually proved they are on good terms.

When Brooks' announced his engagement to KatrĂ­n Tanja DavĂ­Ă°sdĂłttir in December 2024, Julianne celebrated the news, writing on Instagram, "I'm so happy for you both as you step into this beautiful new chapter together. Wishing you both a lifetime of love, laughter, and endless adventures."

Months later, the dancer and her ex-husband, alongside his pregnant now-fiancĂ©e, spent the day together on the lake, posting a pic herself with them with the caption, "Special day on the lake with these three cuties.”

Since their 2015 breakup, the parents to Violet, Seraphina and Samuel have hit the conscious uncoupling trifecta: Joint vacations, shared holidays and public displays of admiration with Ben dubbing his ex "an amazing mother" during a 2016 interview with E! News. 

Nina and Ian may have called it quits in 2013 after three years of dating, but they've remained close friends since then. In 2014, the Vampire Diaries star started dating Nikki Reed and tied the knot later that year. Naturally, Dobrev befriended the Twilight actress.

The two called it quits in July 2016 after five years together. The singer said on SiriusXM's The Howard Stern Show the following October that she's "very close" to Kinney, adding, "He's been my lover and a friend for so long."

The Office's on-and-off pairing remained so tantalizingly close after the series wrapped in 2013 that even Mindy gets why people are still shipping them. "If I was on the outside looking at it, I would think the same thing," she told Good Housekeeping in 2019 of naming him godparent to her kids. "But the truth is that B.J. is so much more like family now than a platonic friend."

The exes had no trouble coparenting their son, Bronx, after finalizing their divorce back in 2011. The Fall Out Boy singer has even said his former wife is "an awesome mom."

So she's over those "7 Things" then? The JoBro musician has said he's "really friendly" with his ex. "We've got a good relationship."

The Dexter stars first met on set in 2006 before things got romantic in 2008. And although they divorced in 2011, Jennifer assured there was "nothing but love and respect" between the exes a few years later. 

Long the gold standard of copacetic exes, the parents to daughters Rumer, Tallulah and Scout remain so tight that the decision to ride out coronavirus stay-at-home orders together in Idaho was a no-brainer. Quarantine dance party anyone?

Some four years after their 2014 divorce, Lopez was still giving her former spouse, dad to her twins Max and Emme, props. "While I was married to Marc, he really helped me with my confidence and he saw where I suffered," she said on a 2018 episode of Sunday Today. "He was like, 'You're a great singer. Don't ever let anybody tell you you're not a great singer.' And I respected him so much 'cause I consider him one of the best singers of all time."

Even if it hasn't been his day, his week, his month or even his year, the actress will be there for her former husband and Scream costar. "I mean, as divorces go, I would say it's one of the better ones. For sure," she shared on Running Wild With Bear Grylls eight years after their 2010 split. Raising daughter Coco, she continued, "We're good co-parents together."

Their real life romance may have fizzled in 2007. However, that doesn't mean the two couldn't heat up the screen in the 2011 movie Bad Teacher.

Sure, the initial few months of their 2013 split were rough going, but the actors have now reached the group vacation stage of their divorce. "I really like her husband and I think he's a great guy," the Twilight alum told LaPalme Magazine of a 2017 trip to Cancun that included Garth, Dave Abrams, Peter's now-fiancée Lily Anne Harrison and their three daughters Luca, Lola and Fiona. As for his relationship with Jennie, he continued, "People come into your life for a reason and relationships can change," he told LaPalme. "Just because we aren't living together doesn't mean you can't love each other."

Despite a surprise separation in September 2012, the couple decided to put on a united front for their children. "As you know, Will and I are very, very good friends," she explained during a 2014 interview with Howard Stern. "We are doing a really good job. I don't think a 10-year marriage constitutes a failure. I think relationships are really tough."

The Grammy winner and her ex-husband—who finalized their divorce in January 2024—have remained on good terms as they continue to parent their son Hayes. In fact, the songwriters live just five minutes apart from one another, which makes co-parenting a breeze.

“Our stops are really easy,” Maren told The Zoe Report in May 2025, “and we’ll have family dinners.”