Surprisingly, These Celebrities Once Dated

Unless you have an encyclopedic knowledge of every celebrity’s relationship history (and let’s be honest, that’s our job) you’d probably be surprised by some people they’ve dated. Here’s a list of some of the most surprising — however brief — celebrity items.

Tom Cruise and Cher

The two got together in the 1980s. Later, when talking to Andy Cohen about it on Watch What Happens Live, Cher ranked Cruise in the “top five” of her lovers.

50 Cent and Chelsea Handler

They briefly dated during 2010. After they split, Handler said, “I’m not gonna date somebody whose name is a number.”

Whoopi Goldberg and Ted Danson

They began an affair in 1992 while filming “Made in America.” At the time, Danson was already married. He and Goldberg eventually broke up two years later.

Ed Norton and Courtney Love

After co-starring in 1996’s The People vs. Larry Flynt, the two dated for a bit. Love called Norton her most stable partner.

Jack White and Renee Zellweger

The White Stripes frontman dated the actress for two years until 2004.

Justin Timberlake and Fergie

They dated briefly in 1998, when Fergie’s band opened for NSync.

Jay Leno and Sharon Osbourne

In Osbourne’s own words, she and Leno had a “flingy wingy” shortly after she moved to the U.S.

Julia Roberts and Kiefer Sutherland

They two actors were even engaged in 1991 until Roberts called it off.

Aubrey Plaza and Michael Cera

The two friends and Scott Pilgrim vs. the World co-stars dated for a year and a half.

Kathy Griffin and Quentin Tarantino

The two dated in 1995. Griffin later recalled, “He was so in love with me,” but said that she never “sealed the deal.”

Madonna and Tupac

After decades of speculation, in 2015, the singer revealed that they had dated in 1994, two years before the rapper died.

Ryan Reynolds and Alanis Morrisette

The two got were engaged in 2004 before calling it off.

Kim Kardashian and Nick Lachey

They briefly dated in 2006 before Kardashian was internationally known.

Fred Savage and Jennifer Love Hewitt

It was only one date. She was 14, he was 16 … and he never called her back.

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