Friendly Celebrity Exes: Hollywood’s Ex-Lovers Who Have Stayed Close

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Friendly Celebrity Exes: Hollywood's Ex-Lovers Who Have Stayed Close

Love lost doesn’t mean friendship lost for all famous exes! Several former celebrity couples have proven that pumping the brakes on their romance doesn’t mean that they can’t become friends afterward. Bruce Willis and Demi Moore’s post-breakup bond has become the golden standard for cordial former lovers. The A-listers got married in 1987 and finalized their divorce in 2000 after having three children: Rumer, Scout and Tallulah. Two decades after their split, the pair spent part of the coronavirus pandemic together in early 2020 while quarantining alongside their daughters in Idaho. (Willis’ wife, Emma Heming, later joined the exes and brought daughters Mabel and Evelyn.) “We have three children whom we will continue to raise together, and we’re probably as close now as we ever were,” the Die Hard star told Rolling Stone in 2000. “We realize we have a lifelong commitment to our kids. Our friendship continues. The institution has been set aside.” [jwplayer LTp6UKJK-zhNYySv2] Cameron Diaz and Justin Timberlake, meanwhile, began dating in 2003 but split in 2007. After calling it quits, the former flames costarred in 2011’s raunchy comedy Bad Teacher — a film that saw the pair’s characters hook up on screen. At the time of Bad Teacher’s release, the “Can’t Stop the Feeling” crooner said that he didn’t feel awkward filming the intimate scene with Diaz. “I didn’t look at it like that,” he previously told Access Hollywood. “We obviously know each other, but I looked at it as a really funny, funny scene that I’ve never seen done before.” Timberlake continued, “What I actually remember was, you know, they got to my closeup for that scene, so I was just kind of by myself — which is hard to imitate in real life. Jake [Kasdan], the director, kept yelling out, ‘OK, more contorted! Uglier face! Flare your nostrils! Curl your lip up … more!’ And I’m trying not to laugh.” Kourtney Kardashian and Scott Disick were also able to come out on the other side after their rocky romantic relationship, which lasted from 2006 and 2015. The exes have established a good friendship and strong coparenting dynamic for their three children, Mason, Penelope and Reign. After splitting from Sofia Richie in late 2020, Disick has spent more time with the Poosh founder, including at her sister Kim Kardashian’s 40th birthday bash that October 2029. A source told Us in November 2020 that Kardashian and Disick’s dynamic has changed. “Kourtney and Scott’s relationship has taken a bit of shift recently — spending more time together and being more kind with each other,” the insider revealed. “Scott has always loved Kourtney, and the door is open on his side in case she ever wants to take their relationship back to a romantic place.” Take a look at more famous ex-lovers, such as Hilary Duff and Mike Comrie, have maintained close relationships after splitting up. [podcast_block]

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Gwyneth Paltrow and Brad Pitt

While the Goop founder told Entertainment Tonight in October 2022 that she and Pitt "weren't friends for a while" following their 1996 split, the pair "found our way back [to one another], probably about 18 or 19 years ago, something like that, and then just kind of stayed in touch over the years."

Paltrow continued: "I adore him. He's an amazing person, and he's a great entrepreneur, and such a creative, and such a good person. I really love him. I'm a big fan."

She added that her husband, Brad Falchuck, is also supportive of her friendly relationship with her former fiancé. "My husband is probably like the least judgmental, most secure man in our relationship, so I think he totally respects [the friendship]," the Oscar winner explained. Probably one of the things that he likes about me is that I believe in conscious uncoupling ... So even though sometimes it can be uncomfortable, I think it's nice to work through it and reconnect with the value that that person brought to your life."

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Chelsea Handler and Jo Koy

Handler announced in July 2022 that she and the stand-up comedian had split after less than one year of dating, but the exes still root for each other. "We're great friends and that's how it will always be," Koy told Entertainment Tonight one month after the breakup announcement.

The Easter Sunday star added, "I'll always champion for her and she'll always champion for me — and we're gonna win, everyone wins."

In September 2022, Koy echoed those sentiments, explaining that it's "not that hard" for him to stay friends with Handler. "It’s healthy," he said during an appearance on The Kelly Clarkson Show at the time. "It’s so healthy and it can work. You guys were friends before, you can be friends after."

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Natasha Lyonne and Fred Armisen

The Russian Doll star confirmed in an April 2022 The Hollywood Reporter profile that she split from the comedian, though they remained on good terms. Armisen even made a surprise cameo during Lyonne’s Saturday Night Live hosting debut one month later.

“You know, Freddie and I, we dated for seven years," Lyonne said in her May 2022 monologue during the season 47 finale. She joked, “We were the only couple with a sex tape that nobody wanted to buy.”

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Clark Gregg and Jennifer Grey

The actors, who tied the knot in July 2001, announced in July 2020 they were calling it quits after nearly 20 years of marriage. Still, Gregg happily promoted his ex's memoir in February 2022.

“4 words u never want to hear [from] ur ex: ‘I’m writing a memoir,’” the Agents of S.H.I.E.L.D. alum jokingly tweeted in February 2022 after Grey announced her book would come out the following May. “So believe me when I say this book is great. It is (like J) wise fearless & funny af & [doesn’t] pull punches.”

The following month, he wished the Dirty Dancing star a happy birthday via his Instagram Story. "You still make beverages come out of my nose. #BestExEver," he captioned a photo of Grey, with whom he shares daughter Stella, born in December 2001.

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Ryan Seacrest and Julianne Hough

The Live With Ryan and Kelly cohost was first linked to Hough in 2010, but he and the Dancing With the Stars alum split in 2013. Nearly a decade later, the two said they remained in touch.

“Jules, just to start, [my cohosts] Sisanie and Tanya have been asking me if this is awkward for me,” the American Idol host said while interviewing his ex-girlfriend and her brother, Derek Hough, during a March 2022 episode of On-Air With Ryan Seacrest. “And I said, ‘Not at all because we’re friends’.”

Seacrest added, “There is nothing uncomfortable about it, because we’ve remained friends.”

Hough agreed, noting, “We’re friends! We chat [a lot].”

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Joe Jonas and Taylor Swift

The teen singing sensations dated from July to October 2008 before he broke up with her over the phone, but the exes eventually managed to become friends with Swift even revealing in 2016 that she regretted calling him out on the Ellen DeGeneres Show right after their breakup.

"That was too much... We laugh about it now but that was some mouthy — yeah, just some teenage stuff there," she told DeGeneres at the time.

The two have been spotted hanging out several times over the years. Jonas and wife Sophie Turner even attended Swift's November 2021 Saturday Night Live performance of "All Too Well." Hours before the performance, the Game of Thrones actress, who has declared herself a massive Swiftie, wore both the scarf and ring from the singer's merchandise line for the Red album and said she was "not fine at all" while listening to the new music.

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Joe Jonas and Demi Lovato

The former Disney Channel stars, who previously dated for four months in 2010, reunited in October 2021 at a Halloween celebration. Jonas shared a selfie of the exes via Instagram Story, alongside a purple heart sticker and even tagged his former flame. Lovato later reshared the snap on their Story.

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Drew Barrymore and Tom Green

Not only did the former couple, who were married from 2001 to 2002, tearfully reunite in a September 2020 episode of The Drew Barrymore Show, but the exes chatted via Instagram Live the following year. “Will you give [your parents] my love?” Barrymore asked in the September 2021 exchange, which Green said that he would “of course” do.

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Kristin Cavallari and Jay Cutler

The twosome announced their split in April 2020 after 10 years together, and although their separation got off to a rocky start, they've worked to put on "a united front" for their three children: Camden, Jaxon and Saylor. "He's their father. That's important and they need to see that from me," Cavallari told Mr. Warburton in May 2021, four months after the former couple posed side by side for a friendly Instagram pic.

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Alex Rodriguez and Cynthia Scurtis

Despite their "very messy" history, the exes became "good friends" in the wake of the retired athlete's split from Jennifer Lopez in April 2021, a source told Us. "He has a lot of respect for her husband and they’ve gotten closer as friends," the insider noted. The duo, who share daughters Natasha and Ella, reunited in June 2021 for a joint workout.

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Miley Cyrus and Cody Simpson

After Cyrus’ 2019 split from now-ex-husband Liam Hemsworth and a brief fling with Kaitlynn Carter, the “Mother’s Daughter” singer moved on with the Australian crooner that October. When their breakup was confirmed in August 2020, Simpson raved about Cyrus’ song “Midnight Sky” and shared a screenshot of their celebratory FaceTime call to his Instagram Story.  “So proud of you,” he wrote over the pic. “Congratulations to the most special of all. Go cop that new new!”

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Mindy Kaling and B.J. Novak

The former Office costars dated on and off while working together on the NBC sitcom during its early days, and they have since become the best of friends. After Kaling gave birth to her first child in 2017, she named the One More Thing author her daughter’s godfather. “The truth is that BJ is so much more like family now than a platonic friend,” she told Good Housekeeping in 2019. “He’s the godfather to my daughter, he comes over like once a week. Sometimes he’ll come over just to hang out with her.”

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Kourtney Kardashian and Scott Disick

The Keeping Up With the Kardashian costars developed a good friendship and coparenting relationship after dating on and off from 2006 to 2015. “I do think we are very lucky to be doing it this way and we can, if we have an issue or something that, you know, one of the kids is going through, we can deal with it together,” Kardashian told Disick in an April 2019 chat for her Poosh brand. “Nobody knows our kids better than us so to be able to do that together and, like, come up with solutions together, I think is, you know, there’s no better [way] … Like, what else could you want.”

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Lisa Bonet and Lenny Kravitz

Bonet and Kravitz, who are parents of daughter Zoë Kravitz, divorced in 1993 after six years of marriage. However, the former couple have forged a close bond as friends, even after the Cosby Show alum married Jason Momoa in 2017. “People can’t believe how tight Jason and I are, or how tight I still am with Zoë’s mom, how we all relate,” Lenny said in Men’s Health’s November 2020 issue. “We just do it because that’s what you do. You let love rule, right? I mean, obviously, after a breakup, it’s work — it takes some work and time, healing and reflection, et cetera. But as far as Jason and I? Literally the moment we met, we were like, ‘Oh, yeah. I love this dude.’”

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Gwyneth Paltrow and Chris Martin

After consciously uncoupling in 2014 and divorcing in 2016, the former A-list pairing developed a strong coparenting relationship. In October 2020, the exes had a beach double date in The Hamptons with Paltrow’s husband, Brad Falchuk, and Martin’s girlfriend, Dakota Johnson. “Chris is a very close friend,” the Goop founder told the Evening Standard in 2019. “I see him every day, I talk to him every day. And it was very difficult, but I think you see in the children that they got through it, so I am proud of us, I really am. We kept to our commitment that we would put the children first.”

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Jennifer Aniston and Brad Pitt

Aniston and Pitt had a dramatic separation in 2005 following rumors of his alleged affair with now-ex-wife Angelina Jolie. Since then, the former pair have become good friends. The Ad Astra actor attended the Friends alum’s 50th birthday bash in 2019, and the exes later congratulated each other backstage at the 2020 Screen Actors Guild Awards following their respective wins. A source told Us in January 2020 that Aniston “appreciates having his support as she would with any close friend in her life, and she is there for him as well.”

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Naomi Watts and Liev Schreiber

Despite splitting in 2016 after 11 years together, Watts and Schreiber have managed to stay on good terms while coparenting their sons, Sasha and Kai. “I’m pretty proud of us, corny as that may sound,” she told Net-A-Porter’s Porter magazine in 2019. “We’ve made it our absolute priority to be good and kind to each other and we’re absolutely committed to that.”

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Alicia Silverstone and Chris Jarecki

Though the Clueless actress filed for divorce from Jarecki in May 2018 after 20 years together, she revealed to Us in November that there's no love lost between them. We both love our son, right? We both want to be with our son and we both love each other too," she said. The vegan enthusiast also revealed that the former pair communicates "every day" in order to raise their son Bear as a family unit. "We’re so good at coparenting with each other." 

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Channing Tatum and Jenna Dewan

Following their split, Tatum and Dewan, who share daughter Everly, told fans in a joint statement in April 2018 that they are “still a family.” A month later, the actor called the dancer “baby” on his Instagram Story for Mother’s Day.  Dewan then sent her ex love on the social media platform that August following the death of his close childhood friend. In October 2018, after Us broke the news they were both in new relationships, the twosome reunited to take Everly trick-or-treating and shared a sweet selfie in their costumes on Instagram.

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Chris Pratt and Anna Faris

The Parks and Rec alum and the Mom star, who split in August 2017 after eight years of marriage, stepped out together for a family stroll with their son, Jack, the following August. Months later, Faris told Marie Claire in May 2018 that the pair “have a great friendship.” In October 2018, Pratt and Faris took Jack trick-or-treating in Los Angeles with their new significant others, Katherine Schwarzenegger and Michael Barrett, respectively. 

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Kristen Stewart and Robert Pattinson

The former couple caught up with each other at Lily-Rose Depp’s birthday party held Chateau Marmont in Los Angeles on June 2, 2018, according to photos obtained by the Daily Mail. The Twilight costars dated for four years before Stewart was spotted kissing her married Snow White director Rupert Sanders in exclusive photos published by Us in July 2012. They gave their romance another try before splitting for good in May 2013.

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Jennifer Lawrence and Darren Aronofsky

The pair first met when the Oscar winner was cast in his movie Mother!, but they’d eventually call it quits in October 2017 after one year of dating. In February 2018, Lawrence admitted in an interview that she still loved him very much and she went on to present him with an award at the BAM Gala that May.

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Prince Harry and Chelsy Davy, Cressida Bonas

The royal invited both his exes to his wedding to Meghan Markle at St George's Chapel in Winsdor Castle on May 19, 2018. Harry and Davy dated on and off for seven years while he romanced Bonas from 2012 to 2014.

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Mariah Carey and Nick Cannon

The former America’s Got Talent host and the songstress, who married in April 2008 but finalized their divorce in late 2016, were spotted enjoying two dinners in a row with their twins, Moroccan and Monroe, in April 2017. They also regularly celebrate holidays together and attend red carpet events.

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Kate Bosworth and Alexander Skarsgard

The former flames, who dated for two years before breaking up in 2011, reunited at an afterparty for the 2018 Met Gala on May 7 where they not only exchanged pleasantries, but also posed for photos together. The actor also complimented his ex while promoting Straw Dogs in 2011. “Kate is such a great actress and she’s so much more than a good-looking Hollywood starlet,” he told BlackBook at the time. “We shared a really special experience on that film.”

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Tobey Maguire and Jennifer Meyer

Despite announcing their split in October 2016 after nine years of marriage, the jewelry designer called Maguire her “best friend” while speaking with Us at the Create & Cultivate 100 Launch in January 2017. The former couple also posed for photos at Gilt.com’s “Jennifer Meyer & Jenna Dewan Tatum Launch Exclusive Jewelry Collection Benefitting Baby2Baby” event in December 2017. They share daughter Ruby and son Otis.

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Lady Gaga and Taylor Kinney

The former couple, who ended their engagement in July 2016 after spending five years together, have remained friendly since their split. Not only did the Chicago Fire actor attend one of her concerts in August 2016, but a source told Us that the former couple “are still very close,” adding, “Gaga and Taylor talk or text every single day and meet up when they’re in the same city, but nothing romantic is happening between them.”

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Drew Barrymore and Will Kopelman

The parents of daughters Olive and Frankie split in March 2016 after four years of marriage. In June 2017, the Santa Clarita Diet alum and Kopelman spent Father’s Day together by visiting The Ice Cream Museum in Los Angeles. Barrymore also penned a sweet message to her ex on Instagram in March 2018, writing, “I say to Will Kopelman thank you for always being the best dad and supporting and enabling me to do what I need and want to do. I know that’s not everyone’s situation. And I never take it for granted. I never had family growing up. And that’s also a support system I cherish every day of my life. I love my family and everyone in it. Because they form these little girls too. And man, did I pick well!”

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Jennifer Garner and Ben Affleck

After announcing they were calling it quits on their 10-year marriage in June 2015, the amicable exes have continued to coparent their kids, Violet, Seraphina and Samuel. The pair lived together on the same property for several months to ease the transition for the children, and have even been spotted on several family vacations together post-split, including a Caribbean getaway two months after Garner finally filed for divorce in April 2017. 

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Cameron Diaz and Justin Timberlake

Despite splitting in late 2006, Diaz and Timberlake were happy to costar in 2011's Bad Teacher. He's "a genius comedian," she gushed to Us.

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Bruce Willis and Demi Moore

Despite divorcing in 1998, Willis and Moore remain close friends alongside his wife, Emma Heming.

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Courteney Cox and David Arquette

After separating in October 2010, the parents agreed to put the needs of their daughter Coco first.

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Kate Hudson and Chris Robinson

Despite divorcing in 2007, Hudson and Robinson remain close friends for the sake of their son Ryder.

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Jermaine Dupri and Janet Jackson

The on-again, off-again couple called it quits in 2009 but have remained friends and associates since their split.

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Avril Lavigne and Deryck Whibley

After three years of marriage, the punk rock duo divorced in 2010. "I am grateful for our time together," Lavigne said. "And I am grateful and blessed for our remaining friendship."

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Debra Messing and Daniel Zelman

The Will & Grace actress filed for divorce from producer Zelman in June 2012 but called him a "dear friend." Earlier this year, she had this to say about their relationship, "We are co-parenting beautifully… We had Thanksgiving together. In my mind, we will be a nuclear family forever." The couple shares a child, Roman Walker Zelman, born in April 2004. 

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Ryan Phillippe and Reese Witherspoon

While Witherspoon is now happily married to Jim Toth, the Big Little Lies actress divorced Phillippe in 2007 after eight years of marriage. Despite their messy divorce, the pair reached a cordial relationship and continued to own property together and hang out at sports games and events supporting their two children, Ava and Deacon.

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Hilary Duff and Mike Comrie

Duff and Comrie announced their separation in January 2014, but their ongoing friendliness had fans wondering if a reconciliation is possible. The pair happily attended the Coachella Music Festival together just three months after their split and coparent their son, Luca, together. 

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Miranda Kerr and Orlando Bloom

Though they split in October 2013, Kerr and Bloom have remained friends and continue to speak highly of one another. "He's really happy and I'm happy," the former Victoria's Secret model told GQ in 2014. "He's a great dad. I'm really lucky to have him in my life." Bloom is the father to the couple's son, Flynn Christopher Bloom, born in January 2011. 

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Kendra Wilkinson and Hugh Hefner

The Playboy mogul famously dated the model during the taping of his mid-2000s show about his three girlfriends, Girls Next Door. Wilkinson had stayed close with Hefner, and even brought her family to the Playboy Mansion for holidays. Following Hefner's death in September 2017, the Kendra on Top star said in a statement to Us, "He changed my life. He made me the person I am today. I couldn’t be more thankful for our friendship and our time together. I will miss him so much but he will be in my heart forever.”

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Jennifer Lopez and Marc Anthony

J. Lo and Anthony officially split up in 2011 after seven years of marriage. The performers have stayed close to parent their twins, Maximilian and Emme.

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Ashlee Simpson and Pete Wentz

Parents of son Bronx, Simpson and Wentz divorced in February 2011, less than three years after their May 2008 wedding. The rockers are on good terms, celebrating their son's birthday together in November 2013 as Wentz explained they have a priority to put their son first. "We are great friends," he added of Simpson. 

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Michael C. Hall and Jennifer Carpenter

The former Dexter costars were married from 2008 to 2011, and continued to work on their Showtime show together after the split. In September 2013, Carpenter opened up about her relationship with Hall, saying, "Our marriage didn't look like anyone else's, and our divorce didn't either, so...I said it before, just because the marriage ended doesn't mean the love did."

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Nina Dobrev and Ian Somerhalder

Dobrev met Somerhalder on the set of their breakout CW series The Vampire Diaries. The pair split in May 2013 after three years together, with an insider telling Us at the time that they "will continue to work together and remain best friends, which is where the relationship started." The prediction was correct as the actors continue to pal around on and offscreen.