The late 1990s were an exciting time in Gwyneth Paltrow’s life.
Not only was the genetically blessed daughter of actress Blythe Danner delivering on her early promise to become a movie star, she got to date two of the most desirable young up-and-coming male actors in Hollywood: Brad Pitt and Ben Affleck.
But a new biography of Paltrow, 52, reveals why these made-for-the-red carpet relationships didn’t work out. It turns out that the Ozarks-reared Pitt, 61, wasn’t quite classy enough for the future Oscar winner, according to the book, “Gwyneth: The Biography,” by Amy Odell, which is excerpted in People. He was “threatened” by her early success and may have been hurt by rumors that she cheated on him, the book also reveals.
Then came Affleck, and Paltrow reportedly loved the sex, Odell wrote. But the “Good Will Hunting” star was already struggling with his addictions to alcohol and gambling, and he sometimes seemed more interested in playing video games than in spending quality time with his glamorous young girlfriend, according to Odell.
The future Goop lifestyle entrepreneur, whose father was filmmaker Bruce Paltrow, grew up as show business royalty in Santa Monica and New York City. Her godfather was Steven Spielberg, and she attended a posh private school in Manhattan, though she barely managed to graduate because she struggled academically, Odell wrote. She enrolled at UC Santa Barbara but soon dropped out to act professionally. She met Pitt in 1994 at an audition for his movie, “Legends of the Fall.” While she didn’t get the part, he later suggested she play his wife in the David Fincher film “Se7en.”
Paltrow happily signed on for “Se7en,” in part because she wanted to date Pitt, Odell wrote. In a 2023 interview with “Call Her Daddy” podcaster Alex Cooper, Paltrow described her attraction as: “Brad was like the sort of major chemistry, love of your life, kind (of hookup).”
Actress Gwyneth Paltrow and actor Brad Pitt arrive at the Academy Awards in Los Angeles, March 25, 1996. (AP Photo/Kevork Djansezian)
As the two dated for the next three years, they became known as the gorgeous, blonde couple who dazzled at movie premieres and other Hollywood events. Paltrow told Cooper that the “romantic” Pitt proposed marriage while they were staying in Argentina, where he was making a movie. But she told Cooper she called off the engagement, saying that at age 24 she was too young to get married.
Odell’s book offers another layer to the reasons Paltrow didn’t want to marry Pitt. While filming “Emma,” the hit 1996 adaptation of the Jane Austen novel, Paltrow expressed doubts to a crew member about whether Pitt was right for her, while admitting she had a crush on Hugh Grant.
“Brad and I had very different upbringings,” she once told an interviewer, according to Odell. “So when we go to restaurants and order caviar, I have to say to Brad, ‘This is beluga and this is osetra.’”
After “Emma” was released and Paltrow got rave reviews, she visited her good friend, makeup artist Kevyn Aucoin and cried about Pitt, Odell wrote. She said he wanted to be with her but seemed to feel threatened by her success and all the attention she received. According to Odell, Aucoin bluntly told Paltrow: “You really need to end this.”
Odell also spoke with two people who recounted a rumor that Paltrow and Pitt broke up after she cheated on “The Fight Club” star with Scottish actor John Hannah, her co-star in the 1998 film, “Sliding Doors.” Paltrow and Pitt never commented publicly on the breakup but she graciously told Howard Stern in 2015 that Pitt “was too good for me.”
382627 05: Actors Ben Affleck, as Buddy Amaral, a hot shot urban ad executive, and Gwyneth Paltrow as Abby Janello, a struggling single mom, act in a scene from Don Ross” “Bounce.” (Photo by Eric Lee/Miramax Films/Newsmakers)
Paltrow began dating Affleck in 1997, the year that “Good Will Hunting” was released and he and his friend, Matt Damon, won acclaim and an Academy Award for co-authoring the screenplay. Paltrow was attracted to Affleck’s intellect, Odell said, and the worked together on “Shakespeare in Love,” the 1998 film that marked the apex of her career.
While Paltrow and Affleck were dating, she spoke openly about how much she enjoyed their sex life and once told Aucoin that she loved it when Affleck engaged in a certain sex act, according to Odell. “Ben was, like, technically excellent,” Paltrow also told Cooper.
But soon after “Shakespeare in Love” opened to “ravishing reviews” in December 1998, Paltrow and Affleck broke up.
“Their physical chemistry couldn’t overcome his self-destructive impulses, which may have even included cheating on her,” Odell wrote. Paltrow reportedly said about the breakup: “I love men, even though they’re lying, cheating scumbags.”
After Paltrow won the best actress Oscar in 1999 — wearing an unfortunately ill-fitting but still famous, Grace Kelly-esque pink ballgown, designed by Ralph Lauren — she decided to focus on her health, Odell wrote. She also reconciled with Affleck, but his addiction issues resurfaced while she took her healthy living practices to a new level: practicing Ashtanga yoga six times a week, meditating daily, and watching her diet. Paltrow and Affleck broke up for good in October 2000.
Paltrow eventually met and married Coldplay frontman Chris Martin in 2003 and had two children, while Pitt married Jennifer Aniston in 2000, then left her for Angelina Jolie in 2005. Both Paltrow and Pitt’s marriages to Martin and Jolie, respectively, ended in 2016. Paltrow is now married to producer Brad Falchuk.
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For his part, Affleck was involved in a high-profile relationship with Jennifer Lopez, which spectacularly ended in 2004. He was married to Jennifer Garner from 2005 to 2018, with whom he had three children, then reunited with Lopez for another high-flying, two-year marriage that ended earlier this year.
Affleck’s struggles with alcohol addiction continued until recently and were widely covered by the media. The same goes for Pitt, and both men have opened up in interviews about getting sober in recent years through the help of 12-step programs.