Tobey Maguire reunites with ex Jennifer Meyer and daughter in rare photo... 5 years after finalizing divorce
Tobey Maguire was ever the proud dad as he celebrated his daughter Ruby's high school graduation on Monday with ex-wife Jennifer Meyer.
The Spider-Man actor, 49, was pictured reuniting with his former spouse, 48, in rare but sweet photos shared to her Instagram, five years after they finalized their divorce.
In one photo captured at the ceremony, the exes — who also share 16-year-old son Otis — were seen embracing the 18-year-old, who stood between them holding a bouquet of pink roses.
Both parents had big smiles on their faces, with Jennifer — who got engaged to billionaire heir Geoffrey Ogunlesi last year — holding her daughter's diploma from the Crossroads School for Arts & Sciences in Santa Monica, California.
In another snap Ruby was pictured beaming as she stood surrounded by a number of her family members, including her famous dad and jewelry designer mom.
'Congratulations Ruby!!!!! ♥️ Graduate of our dreams. We are so proud of you in every way. We love love love love love you baby♥️' Jennifer wrote in her caption.
Leonardo DiCaprio's close pal opted for a casual cool look for the school event, rocking a grey t-shirt, black sunglasses and a baseball hat.
Jennifer looked chic in a green spaghetti strap dress.
Meanwhile Ruby proudly wore her cap and gown, with one snap showing her at home posing in front of a giant pink ballon sign spelling out her name and graduation year.
Yet another snap saw the mother and daughter posing together and smiling for the camera.
Fashion designer Rachel Zoe commented on Jennifer's post, writing 'We love you RUBY!!!!'
Australian actress Isla Fisher added, 'Wha? That's gone so fast.... Mazel Tov!'
Teen Witch star Mandy Ingber wrote, 'Ruby is gorgeous. And I love seeing Tobey. Xoxoxo congratulations to you. You did it! ❤️❤️❤️ makes me so happy to see.'
Amazon founder Jeff Bezos' fiancée Lauren Sanchez also commented, writing, 'Congratulations sweet girl ❤️❤️❤️.'
Ruby's not the only child of famous parents graduating from Crossroads this year.
Grey's Anatomy star Patrick Dempsey's twin sons Darby and Sullivan were also among the 2025 graduates.
Tobey and Jennifer divorced in 2020, ending their nine-year marriage.
They had initially separated in 2016, sharing a statement that read: 'After much soul searching and consideration we have made the decision to separate as a couple. As devoted parents, our first priority remains raising our children together with enduring love, respect and friendship.'
She has since moved on with billionaire heir Geoffrey, who is the son of Nigerian billionaire Adebayo Ogunlesi.
In December, Jennifer was spotted with her fiance and her son during a rare outing together.
The trio were seen shopping for a Christmas tree.
Jennifer and Geoffrey became engaged in September.
'YES!!!' the mom-of-two wrote in the caption of the Instagram snap, along with a black heart emoji, the infinity symbol, and sparkling stars emoji.
Jennifer, whose best pals are Jennifer Aniston and Courteney Cox, and Geoffrey went red carpet official in November 2023, after dating for several months.
Jen is the daughter Ron Meyer, the cofounder of CAA, and former executive at NBC, COO/President of Universal.
Her red carpet debut with Geoffrey came seven years after she split from Tobey, and three years after she filed for divorce.
Meanwhile Tobey was spotted getting cozy with 22-year-old Danish model Mona Tougaard a month after Meyer announced her engagement.
Last summer he was linked to a string of young ladies while vacationing in Europe and New York City.
Jennifer and Tobey met in 2003 while he was shooting Seabiscuit. They were engaged three years later, and welcomed their daughter Ruby in November 2006.
They went on to marry the following year, and welcomed their second child, son Otis, in 2009.
Meyer has credited 'angel' Gwyneth Paltrow for her amicable divorce from the actor.
Paltrow, 51 was widely ridiculed for announcing her divorce from Coldplay star Chris Martin, 47, as a 'conscious uncoupling' in 2014.
But Meyer said the actress' amicable split helped her navigate her own divorce from Maguire.
Speaking on the Broad Ideas podcast, jewelry designer Meyer said: 'Right when Tobey and I were starting to break up, I watched what Gwyneth Paltrow was starting to do with Chris — this conscious uncoupling that everyone was making fun of.'
'I got to see it firsthand, and it was the most beautiful thing that I had ever witnessed two human beings go through. She was so loving and kind and open to him and she created this family.'
'I was like, "Wow, that's not what I was taught growing up. I was taught that divorce was ugly … bad and would never be good."'
Meyer asked Paltrow: 'How did you do that? Please, what do I do? Because we're just starting to break up, and it's feeling very scary. … How can we come together for [these] human[s] we both created that we love? What do we do?'
Meyer added that Paltrow introduced her to Dr. Habib Sadeghi: 'She didn't tell me their process, she didn't tell me anything.'
Meyer said she had 'hit the jackpot of ex-husbands' with Maguire and added the pair were still 'best friends' years after their divorce.
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