Keira Knightley dated the 50 shades actor from 2003-2005.
The pair were often seen looking loved up at events together.
These iconic actors actually lived together for four years in the 80s.
They met on the set of the 1981 film Excalibur.
This pair of actors met when they were both relatively new to the scene in 2001.
They were together for five years and even considered getting married before they eventually broke up in 2006.
These two singers enjoyed a casual relationship while they were in 'NSync. and the Black Eyed Peas respectively.
Fergie said in 2003: 'We went to Hawaii together, but we were never serious. He was Mr. Right Now.'
Kidman and Kravitz were together from 2003 and 2005.
Kidman once revealed they were even engaged!
Kunis and Culkin were reportedly together for nine years, between 2002 and 2011.
Kunis told Woman's Health that they ‘grew up together’.
Despite their 16 year age gap, this pair once dated.
When asked to rank her lovers, she once said that he ‘was in the top five’.
This pair met on the set of Midnight in Paris.
They were together from 2011 - 2013, but reportedly broke up because they weren't on the same page about their future: McAdams wanted to settle down while Sheen wanted to focus on his career.
Gyllenhaal and Portman dated for a short time in 2006, and have stayed friends ever since.
They even worked together three years later when they co-starred in the psychological drama Brothers in 2009.
Madonna revealed in 2015 that she had dated Tupac in 1994.
She said the rapper, who was killed in 1996, got her 'all riled up on life in general'.
Diaz and Timberlake were together from 2003 - 2007.
Many speculated that the couple's downfall began when the stunning actress Scarlett Johansson appeared in Timberlake's 2006 music video, What Goes Around ... Comes Around. However, the pair have remained friends.
Duff met the Good Charlotte band member when she was 16. Despite their 9 year age difference, the pair started dating in 2004.
They dated for two years, and Duff later told Cosmopolitan: ‘I had a 26-year-old boyfriend. So everyone can make their own assumptions about what I was doing.’
This pair dated for eight years after meeting in 1984 on the set of the film Firstborn.
Robert Downey Junior opened up about their breakup: 'I liked to drink, and I had a drug problem, and that didn't jibe with Sarah Jessica, because it is the furthest thing from what she is. She tried to help me. She was so miffed when I didn't get my act together.'
Nick Cannon has dated his fair share of powerful women, including Mariah Carey. However, he has also been in a relationship with a Kardashian who apparently ‘broke his heart.’
From 2006 to 2007, the comedian dated none other than the Queen Kardashian—Kim. He talked about their relationship in 2021 while on Drink Champs and said he was ‘really into her' and that she broke his heart.
The two actors got close when they were filming Me, Myself & Irene and ended up dating for only about a year.
The one year of dating turned out to have quite an impact on Carrey as he still talks about her very fondly. He's even gone as far as to say that she was ‘the great love of his life’.
