Blast From The Past: Former Celebrity Couples

You know how looking back on photos of past relationships can be, well, cringe-worthy? These former celebrity couples are no exception. From Gwyneth and Brad Pitt to Penelope Cruise and Tom Cruise, we’re reminding you of fabulous celebrity couples from yesteryear. This is one walk down memory lane you won’t want to miss.

Gwyneth Paltrow and Ben Affleck

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W Magazine

Gwyneth Paltrow has been a Hollywood mainstay since she first entered our screens in the early 1990s. Her first film, Shout, co-starred John Travolta, and soon after Gwyneth was cast by Steven Speilberg in Hook (1991) as the young Wendy Darling. Paltrow’s on-again-off-again relationship with Ben Affleck spanned from 1997 to 2000, and though the two were never serious enough to get engaged, the actress did thank Ben in her Oscars speech in 1999 after winning for their mutual film Shakespeare in Love.

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Marie Claire Australia

In 1996, Paltrow got engaged to boyfriend Brad Pitt but a year later they ended the relationship. Today Paltrow is a lifestyle-guru/goddess of sorts, and in 2015 reflected on her dating history, saying of Pitt, “You can’t make that decision [to get married] when you’re 22 years old… I wasn’t ready, and he was too good for me.” Since her engagement to Brad Pitt, Paltrow married Coldplay frontman Chris Martin in 2003 (and got divorced in 2016), and in 2018 married Brad Falchuk a director and producer. One thing’s for sure- we’d love to take a peek at her diary!