Hollywood’s friendliest exes: The former flames who have remained close after splitting as Tobey Maguire officiates ex Jennifer Meyer’s wedding to billionaire heir

DAILYMAIL.COM • 6h ago

By CAROLINE PEACOCK, SHOWBUSINESS REPORTER 15:24 12 Oct 2026, updated 15:32 12 Oct 2026

Hollywood is known for high-profile breakups, with some of the most dramatic and scandalous splits making headlines over the years.

From explosive rows and legal disputes to drawn-out custody battles, it’s little wonder some celebrities choose to cut all contact once a relationship comes to an end.

But not every romance has to end on bad terms. Some former couples have shown that calling time on a relationship doesn’t mean a friendship has to be off the cards.

Whether they’re united by their children, shared memories or years spent together, these stars have proved that sometimes, being friends works better than being lovers.

Jennifer Garner, Orlando Bloom and Demi Moore are among the famous faces who have managed to maintain amicable relationships with their former partners.

And Tobey Maguire was front and centre as his ex-wife, Jennifer Meyer, celebrated a major milestone on Saturday.

Here, the Daily Mail takes a look at the stars who have remained close to their former flames, proving that even when the romance fades, a lasting friendship can remain.

Tobey and Jennifer met in 2003 when he was shooting the period sports drama Seabiscuit at Universal Studios, where Meyer’s father, Ron Meyer, served as president and chief operating officer from 1995 to 2013.

The former couple welcomed their daughter Ruby in November that year, and tied the knot in Kona, Hawaii, in September 2007, before welcoming son Otis in May 2009.

In October 2016, they announced their split after nine years of marriage.

‘After much soul-searching and consideration, we have made the decision to separate as a couple,’ they said in a joint statement at the time.

‘As devoted parents, our first priority remains raising our children together with enduring love, respect and friendship.’

Four years later, Jennifer filed for divorce in October 2020.

They were legally declared single on September 21, according to court documents obtained by Page Six.

The documents read: ‘Judgment of dissolution is entered. Marital or domestic partnership status is terminated, and the parties are restored to the status of single persons.’

Tobey and Jennifer bifurcated their marital status, meaning the exes still need to resolve ‘other issues’ in their divorce, though the specifics of those outstanding matters are not known.

The judgment was filed with the Los Angeles Superior Court on October 1.

‘The Court shall reserve jurisdiction to hear and determine all issues raised by the Petition and Response herein, other than dissolution of the parties’ marital status,’ the court documents stated.

The pair also agreed to have a private judge oversee any outstanding disagreements as they work towards finalising a larger settlement, Page Six previously reported.

On Saturday, Tobey stood front and centre as Jennifer wed music executive Geoffrey Ogunlesi.

In a very unconventional show of friendliness, the Great Gatsby star, 51, officiated the star-studded ceremony at the Four Seasons Resort Lanai in Hawaii.

Dressed in a neat black suit, Maguire beamed as he led the ceremony from a piece of paper.

Jennifer previously admitted she and Tobey are still very close.

Appearing on the Broad Ideas with Rachel Bilson + Olivia Allen podcast in July 2024, she explained: ‘Tobey is my best friend now. We travel together, we do every holiday together, I’m so lucky.

‘I literally have the best ex-husband in the world, and I hit the jackpot. I honestly don’t know what I would do without him in my life. I ride for him so hard. He’s so phenomenal.’

Ben Affleck and Jennifer Garner shocked Hollywood back in 2015 when they announced their marriage was over after ten years together.

Just days later, the pair opted to jet off to the Bahamas with their three children to weather the storm, and appeared visibly tense during the break.

‘The family felt it was important to be together and they were together. The family is united and, no matter what, will protect the kids,’ an insider told PEOPLE at the time.

In later years, Ben opened up about his co-parenting relationship with his ex Jennifer, telling the publication: ‘I’m very grateful and respectful of her. Our marriage didn’t work, and that’s difficult.

‘Both of us really believe that it’s important for kids to see their parents respect one another and get along, whether they’re together or not.’

Most recently, Ben said there is ‘nothing salacious’ about his personal life as he has remained on good terms with Jennifer.

Ben went on to marry his ex Jennifer Lopez in 2022 after the pair stunned fans by rekindling their Noughties romance, but she filed for divorce just two years later.

The Oscar winner said: ‘I work hard, and then I go home and pick up the kids from school.

‘We have dinner if they agree to hang out with me. They’re with me for a week, then with their mom for a week.’

Speaking to Variety, Ben described his co-parenting relationship with Jennifer G as ‘really wonderful’, and credited his children for being the reason he’s continued working in Hollywood.

‘I’m divorced, I have shared custody, and I don’t want to miss these years. My kids are here, and their life is flying by. I don’t want to have to be in Shreveport or New Mexico in order to work.’

Ben and Jennifer had initially been slated to co-star in his new film Animals, with Kerry Washington later being cast to replace Garner.

The former couple would have portrayed a rocky marriage on the screen.

‘I talked to Jen, and she was like, “We don’t wanna do that. You just get baggage”,’ he said of their conversation during an interview with Entertainment Weekly.

However, Ben shared how he does want the chance to collaborate with his ex-wife in the future.

‘I would love to work with her, frankly. She’s fabulous, and we’re really good friends, and I’m profoundly grateful to her, and we have a great thing.’

In October 2002, Gwyneth Paltrow and Chris Martin met three weeks after the death of her father, Bruce Paltrow – after which Chris penned Fix You to help with her grief.

They married in December 2003 in a ceremony at a hotel in southern California, during which she was pregnant with Apple. She was born the following year, while they welcomed son Moses two years later in 2006.

His unique name was inspired by a song Chris wrote for Gwyneth. Simon Pegg and Coldplay’s Jonny Buckland are her daughter’s godfathers.

Gwyneth pared back her workload after becoming a mother and revealed she also suffered from postpartum depression after the birth of her younger child in 2006.

The couple then stunned the showbiz world when, in March 2014, she announced that they had separated after ten years of marriage, describing the process as ‘conscious uncoupling’.

In her official announcement, she had her doctor, Habib Sadeghi, and his dentist wife, Sherry Sami, explain conscious uncoupling as ‘the ability to understand that every irritation and argument [within a marriage] was a signal to look inside ourselves and identify a negative internal object that needed healing.

Habib explained: ‘From this perspective, there are no bad guys, just two people, it’s about people as individuals, not just the relationship.’ In April 2015, Paltrow filed for divorce, which was finalised on July 14, 2016.

The duo maintained a firm friendship, and in 2014, she began dating producer Brad Falchuk, whom she met on the set of Glee in 2010.

They announced their engagement in January 2018 and tied the knot in September that year.

Chris went on to date Dakota Johnson, whom he met through mutual friends and have ‘never really left each other’ since, the actress told Vanity Fair in June 2022.

They were first spotted together in 2017, the year after the musician’s divorce from Oscar-winning actress Gwyneth. However, it was not initially clear if the couple were dating, or just close.

In June 2019, the pair had a wobble, rumoured to be a result of the Coldplay frontman pushing for them to have children.

This was a leap Dakota, in her professional prime, was reportedly not willing to take. However, before summer was up, they were back together.

Dakota recently discussed her love for her stepchildren.

She told Bustle: ‘I love those kids like my life depends on it. With all my heart.’

As a member of a large blended family herself, Dakota – who was recently spotted in Malibu – has learned to embrace connections that aren’t blood-related.

When the reporter brought up a photo Gwyneth posted of her and Dakota, she said: ‘I grew up in a family that was so big, and I just believe in the saying “Blood is thicker than water”,’ she explained.

‘The actual saying is “The blood of the covenant is thicker than the water of the womb,” which means that the connections with people you choose are more solid than the connections to the people you’re actually born to.’

On their friendship, she went on: ”I think because I grew up in [having a blended family], it’s come more naturally, but I wouldn’t have it any other way really. I really wouldn’t. I love it. It feels very honest. It feels really authentic…

Adding her own take on things, Gwyneth said: ‘We’re actually very good friends. I love her so much. She’s an adorable, wonderful person.’

In 2020, she once again spoke about Dakota, saying: ‘I can see how it would seem weird because it’s sort of unconventional. But I think, in this case, just having passed through it iteratively, I just adore her.’

Demi Moore and Bruce Willis were married from 1987 to 2000 and share daughters Rumer, 38, Scout, 35, and Tallulah, 32.

Though Demi and Bruce parted ways years ago, love found them both again.

Demi married Ashton Kutcher in 2005, though their marriage ended with a finalised divorce in 2013, while Bruce found lasting happiness with model Emma Heming, and together they have two daughters, Mabel, 14, and Evelyn, 12.

But despite the shifting tides of romance, Demi insisted: ‘I am most grateful that regardless of what the outside relationship has been, we have maintained being a family in various forms,’ she told People.

‘The foundation of making our children our priority has never wavered.’

These days, the actress counts ‘my family, including my four-legged family, my children and all of the incredible, loving people in my life’ among her greatest blessings.

‘I feel really so lucky,’ she told the outlet.

This heartfelt moment comes after Demi revealed she visits Bruce weekly, further emphasising her unwavering commitment to their family.

Bruce notably retired from acting in 2022 after he was diagnosed with aphasia. The following year, his family announced that it had progressed to FTD (frontotemporal dementia).

‘We will always be a family, just in a different form,’ she told Variety.

‘I hope it’s encouraging for others to see that there’s a different way to do things,’ Demi said of the friendship, she and Bruce still have after their divorce.

‘There is life after divorce. There is a way to co-parent with love,’ Demi explained.

Since splitting in 2015, Kourtney and Scott have continued to maintain their strong family unit, with the latter also staying close pals with the rest of the Kardashian clan.

In 2019, Kourtney flew to Finland with her three children to celebrate her 40th birthday, with Scott and his then-girlfriend Sofia Richie joining them.

Weeks after the trip, Kourtney set tongues wagging when she posted a cryptic message on her Instagram Stories.

‘Sometimes the universe will send an ex back into your life just to see if you are still a stupid heaux,’ read the quote, which is from ‘Trap Yoga Bae’ Britteny Floyd-Mayo.

Kourtney and Scott also took their family on a trip to Mexico in 2018 and at the time a fan declared the break was an example of ‘co-parenting done right’.

Sister Khloe then proceeded to give the praise her seal of approval, writing: ‘Beyond proud of all of them!!!! This is LOVE!! Your children before anything else!! All amazing adults right right!!!’

Kourtney went on to tie the knot with Blink-182 drummer Travis Barker, and they welcomed their first child, son Rocky, in November 2023.

Since their split in 2019, Bradley and Irina have continued to be the picture of friendly exes, with both settling into co-parenting their daughter Lea, nine.

In 2022, the pair even sparked rumours of a reconciliation after the model shared a slew of holiday snaps of them during a family trip to the Bahamas.

In a gallery of snaps posted on Instagram, one image showed a bikini-clad Irina and Bradley happily posing together, and she captioned with a heart emoji.

The following year, the pair then enjoyed a family trip to Venice with their daughter Lea, and at the time a source told DailyMail.com that Irina’s then-boyfriend Tom Brady was ‘not one bit jealous’ about her close relationship with ex Bradley.

Irina and Bradley are such close co-parents that they have made sure to live just blocks apart in New York in order to raise their daughter.

‘He’s a full-on, hands-on dad – no nanny,’ Irina told Highsnobiety. ‘Lea went on holiday with him for almost two weeks – I didn’t call them once.’

Miranda and Orlando first started dating in 2007, before marrying in 2010, with the pair breaking up three years later.

The model and businesswoman, 43, who shares son Flynn, 15, with the Pirates of the Caribbean actor, 49, branded their set up as ‘harmonious’.

Earlier this year, she shared a rare insight into her co-parenting relationship with ex Orlando.

Sitting down with Paul C Brunson’s We Need to Talk podcast, Miranda said: ‘From day one, Orlando and I had done a lot of spiritual work, and forgiveness was a big part of that, forgiving each other, forgiving ourselves, creating peace within the situation.

‘And we both knew that the relationship was not bringing out the best in each other.’

She continued: ‘So when we made that decision to separate, I said to him, “Let’s always put the needs of Flynn first”. Like, let’s not make it about us.

‘Let’s make it about what’s in the best interest for Flynn. But at the same time, let’s make sure that we completely forgive each other, make peace with each other, because otherwise it really weighs on you.’

Miranda, who is now married to husband Evan Spiegel, has three other children with the business leader; Hart, eight, Myles, six, and 23-month-old Pierre.

Despite moving on, the star added she always knew Orlando would be in her life, so wanted it to be as ‘harmonious’ as possible.

She said: ‘When you have a child with someone else, they’re always going to be that person’s parent for the rest of their life, and there are going to be situations when you’re going to need to talk if you like it or not.

‘So why not make it harmonious? Why not make it more peaceful?’

Last year Miranda proved how close both her family and Orlando’s are, as she addressed his split from Katy Perry after nine years.

Speaking on Australia’s KIIS FM’s Kyle and Jackie O show in September, Miranda confirmed the couple’s split was amicable.

‘Was it mutual?’ host Kyle Sandilands asked.

‘Yes, and I actually just saw them both on the weekend. We were celebrating [their daughter] Daisy’s birthday,’ Miranda revealed.

‘We’re one big, happy family. Katy is amazing; I love her. And Orlando obviously,’ she continued, before adding: ‘If you do have animosity, it only hurts yourself.’

Katy and Orlando were first linked when they attended a Golden Globes afterparty together in January 2016, and have been on-and-off in the intervening years.

Early in their romance, they hit the headlines when Orlando was spotted completely naked during a paddle-boarding romp with Katy in Sardinia.

They broke up in 2017 but had reignited their romance by the following year.

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