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19 March 2024

Strange Dates: Crazy Hollywood hook-ups

Published

Past Loves

Tom Cruise and Cher

As Tom was trying to make a name for himself in the '80s, and Cher was already topping the Billboard charts, they briefly dated.

(Photo by Getty Images)

Brooke Shields and Nicolas Cage

Back in the 1980s, America's sweetheart Shields dated Cage. The two even went public with their relationship at the 1987 premiere of his film "Moonstruck." The relationship fizzled out after a year.

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Brad Pitt and Christina Applegate

The "Married with Children" star walked out on Brad Pitt at the 1989 MTV Movie Awards.

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Everyone remembers Demi Moore with Bruce Willis, but did you know she dated Emilio Estevez before Bruce?

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Nick Lachey and Kim Kardashian

A few months after his very public breakup with Jessica Simpson in late 2005, Nick Lachey started seeing then no-name, Kim Kardashian. The romance only lasted a few months.

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Ted Danson and Whoopi Goldberg

According to people on set, the chemistry between these two wasn't only onscreen for "Made in America" in 1989.

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Tom Cruise and Sofia Vergara

Fans may have been a bit shocked when Tom Cruise shacked up with Katie Holmes in 2005, but just a few months before Katie, Tom was seen out and about with Columbian hottie Sofia Vergara.

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Ryan Gosling and Sandra Bullock

Sandra Bullock, 47, had a May-December romance with Ryan Gosling, 30, in 2001.

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Kiefer Sutherland and Julia Roberts

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Charlie Sheen and Kelly Preston

The former “Two and a Half Men” star was engaged to Kelly Preston in 1990, but their courtship ended soon after he accidentally shot her in the leg.

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Juliette Lewis and Brad Pitt

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Sean Penn and Madonna

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Sarah Jessica Parker and Robert Downey Jr.

(Photo by Getty Images)