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  1. Home
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  3. Celebrities You May Have Forgot Dated At One Point!

Celebrities You May Have Forgot Dated At One Point!

Amanda Stanford / May 26, 2024 - 09:00 pm

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Actor Macaulay Culkin and actress Mila Kunis attend the launch of the "uBid for Hurricane Relief" charity auction and benefit at the Empire Ballroom 2005
(© Getty Images)

Mila Kunis and Macaulay Culkin

It wasn't just puppy love for these two child stars! Mila Kunis and Macaulay Culkin dated from 2002 until 2011.

Kunis and Culkin were just 18 and 21 when they began dating, and Kunis still speaks highly of the Home Alone actor, saying that they grew up together and shared many high and low moments.

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Actress Rachel McAdams and Michael Sheen arrive at the 'Sleeping Beauty' premiere during the 64th Annual Cannes Film Festival, 2011.
(© Getty Images)

Rachel McAdams and Michael Sheen

It's nearly impossible for anyone to not fall in love with Rachel McAdams on set! Michael Sheen is no exception.

The two met while filming Midnight In Paris, and dated from 2011 to 2013. McAdams revealed that they never spent more than 3 weeks apart at a time, regardless of their filming schedules. 

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Alanis Morissette and Ryan Reynolds attend the New York Premiere of "De-Lovely" 2004
(© Getty Images)

Alanis Morissette and Ryan Reynolds

The idea that Ryan Reynolds dated any one other than Blake Lively is disturbing!

Alanis Morissette met the Deadpool actor in 2002 at Drew Barrymore's birthday party, and announced their engagement in 2004. The pair split up before the nuptials actually took place. 

DON'T MISS: RYAN REYNOLDS HAILS 'DEADPOOL' AS HIS GREATEST GIG EVER

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Cameron Diaz and Justin Timberlake attend the premiere of "Bad Teacher"  2011
(© Getty Images)

Cameron Diaz and Justin Timberlake

Justin Timberlake and Cameron Diaz met back in 2003 at the Nickelodeon Kids' Choice Awards, and dated until 2007. Diaz followed Timberlake on his *NSYNC tour before moving on to movie projects. 

The two worked on Shrek the Third before they announced their split. According to Diaz it was mutual, and the two have remained friendly to this day. 

RELATED: CAMERON DIAZ IS LOVING BEING A NEW MOM, AND SHARES HER HUBBY IS THE BEST FATHER!

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Richard Gere and Cindy Crawford at the 65th Annual Academy Awards, 1993
(© imago images / Cinema Publishers Collection)

Richard Gere and Cindy Crawford

Cindy Crawford and Richard Gere met back in 1988 at a mutual friend's BBQ.

Despite Crawford being only 22 to Gere's 39, the two hit it off and got married in 1991. Unfortunately they called for divorce in 1995, before Crawford got re-married and had two children, Kia and Presley Gerber. 

RELATED: CINDY CRAWFORD SHARES INTIMATE PHOTO OF HER HOME BIRTH, AND REACHES OUT TO WOMEN PREGNANT AMID CORONA VIRUS PANDEMIC

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Tom Cruise and Cher 1985
(© imago images / ZUMA Press)

Tom Cruise and Cher

Wow, who would have thought that Cher and Tom Cruise had a steamy romance!

Despite the 16 year age difference, Cher revealed on Watch What Happens Live With Andy Cohen, that she thinks the relationship could have gone far, as she was "crazy about him". She was also quick to note that Cruise was in her "top 5 best lovers." 

RELATED: A LOOK AT CHER'S CAREER THEN & NOW

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Sandra Bullock and Ryan Gosling arrive at the Festival Palace before the screening of the film " Murder by Numbers" at the 55th International Film Festival in Cannes 2002
(© Getty Images)

Sandra Bullock and Ryan Gosling

While it may have only lasted a year, Sandra Bullock lived every Notebook fantasy, and dated the much loved Ryan Gosling. The two met while filming Murder by Numbers, and started their relationship soon after.

Gosling noted that Bullock was "one of the greatest girlfriend's" he's ever had, and that he thinks it will be hard to find someone better. Of course, Gosling hadn't met his current wife, Eva Mendes yet. 

DON'T MISS: DID RYAN GOSLING ALMOST BECOME A BACKSTREET BOY?

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Janet Jackson and Matthew McConaughey
(© Getty Images)

Janet Jackson and Matthew McConaughey

Janet Jackson and sweet boy from the south, Matthew McConaughey had a short lived romance in 2002, after meeting at the Grammy's.

Although McConaughey denied at the time they were dating, Jackson mentioned it briefly in 2006, saying that they dated "just for a minute."

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Kim Kardashian and Nick Cannon arrive at the William Rast Spring 2007 "Street Sexy" fashion show, 2006
(© Getty Images)

Kim Kardashian and Nick Cannon

Lest we forget the early 2000's B-list power couple! Before Kim Kardashian was the ultra famous reality star she is now, she was the celebrity stylist that dated Nick Cannon. 

Apparently the two only broke up because of Kardashian's sex tape with Ray J. surfaced. The scandal affected Cannon so much that he refused to be intimate with his next girlfriend, Mariah Carey until their wedding night in 2008.

DON'T MISS: KIM KARDASHIAN, NAOMI CAMPBELL AND CHER GRACE THE COVER 'CR FASHION BOOK', TALK SOCIAL JUSTICE

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Jennifer Aniston and Paul Rudd arrive at the premiere of Universal Pictures' "Wanderlust" 2012
(© Getty Images)

Jennifer Aniston and Paul Rudd

Jennifer Aniston and Paul Rudd have appeared in countless films over the years, so it came as no surprise to anyone they decided to try their hands at a romance.

The two only had a brief fling while they filmed Object of My Affection, but Aniston said that it's never been weird kissing her co-star. As Rudd put it, they have "been making out for decades".

RELATED: PAUL RUDD'S BEST ROLES

Load more

The dating pool in Hollywood seems pretty small, and once upon a time, believe it or not, these A-listers gave romance a shot! Here are some blast-from-the-past couples!

Stars You May Have Forgot Dated!

Enjoy!

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