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Gwyneth Paltrow and Madonna's friendship blossomed in the late 80s when her father, TV producer Bruce Paltrow, introduced her to Madonna, who was then married to Sean Penn, the son of director Leo Penn.
The two women developed a close bond as the Iron Man actress grew older.
By the time Gwyneth was living in London with her first husband Chris Martin, who tied the knot in 2003, she and the Material Girl singer were often seen working out together.
According to a new sensational book, Gwyneth: The Biography, by Amy Odell, the duo later had an intense falling out.
As per an excerpt from the page-turner, "Their relationship reached a breaking point when Madonna showed up to an island where Gwyneth and Martin were vacationing."
Amy, who interviewed over 220 people for the biography, penned, "Madonna seemed to know that Gwyneth would be there, which Gwyneth seemed to find strange.”
"Madonna then insisted Gwyneth and Martin join her for a big group dinner at a long table where Madonna went off on her daughter, Lourdes."
The Coldplay frontman and the 52-year-old actress found the singer's behaviour "disgusted," and Chris declared that he "can't be around this woman any more."
While neither of the women have spoken about the friendship fallout, Gwyneth credited her former friend in 2008 for helping her navigate postpartum depression.
During an appearance on The Oprah Winfrey Show, the Seven actress said Madonna urged her to see the "bigger picture" amid her struggles.
Notably, Gwyneth: The Biography is set to release on July 29 and is currently available for preorder.