1. Sandra Bullock and Ryan Gosling Francois Guillot / Staff Back in 2002, long before Birdbox, Sandra dated her Murder By Numbers co-star. Their relationship got a lot of attention because of the 16 year age gap between the two, and it lasted almost two years. 2. Madonna and Tupac View this photo on Instagram instagram.com In 2015, Madonna confirmed the decade long rumour that she and Tupac had dated. They had a relationship from 1994 to 1995, a year before Tupac was killed. 3. Mila Kunis and Macaulay Culkin Ethan Miller / Getty Images It's hard to picture Mila with anyone other than Ashton Kutcher, but she had an eight-year-long relationship with everyone's favourite child star Macaulay Culkin. 4. Matthew McConaughey and Janet Jackson Hector Mata / Getty This unlikely couple happened way back in 2002, but their short relationship wasn't confirmed by Janet until 2006. 5. Tom Cruise and Penélope Cruz Kevin Winter / Getty Images These two were one of hottest couples of the early noughties – they dated for three years after meeting on the set of Vanilla Sky in 2001. 6. Jessic Biel and Chris Evans Vince Bucci / Getty Images Before he won our hearts as Captain America, Chris Evans won Jessica Biel's heart – the pair were in an on-off relationship from 2001 to 2006. 7. Kylie Jenner and Jaden Smith Frederick M. Brown / Stringer These two were teen sweethearts back in 2013. Jaden even attended Kim and Kanye's wedding in Florence! 8. Cameron Diaz and Justin Timberlake Carlos Alvarez / Getty Images These two got together after meeting at the Nickelodeon Kids’ Choice Awards back in 2003. They dated for four years and starred in Bad Teachers together after their breakup. 9. Emily Blunt and Michael Bublé Evan Agostini / Getty Images These two dated from 2005 to 2008 and were very private about the details of their relationship. 10. Kim Kardashian and Nick Cannon Ethan Miller / Getty Images Back in 2006, long before Kim settled into motherhood, she had a relationship with Nick Cannon. 11. Jennifer Lopez and Ben Affleck Doug Kanter / Getty Images Bennifer were together from 2002 to 2004, and they were even engaged! 12. Jennifer Lopez and P. Diddy Henny Ray Abrams / Getty Images J.Lo also dated P. Diddy from 1999 to 2001, back when he was known as Puff Daddy. 13. Katy Perry and Russell Brand Carlos Alvarez / Stringer Not only did these two date, but they were married for almost two years from 2010 to 2012. 14. Michael Cera and Aubrey Plaza Kevin Winter / Getty Images These two stars dated for a year and a half after starring in Scott Pilgrim Vs. The World in 2009, and they very nearly eloped in Las Vegas! 15. Renée Zellweger and Jim Carrey Jim Ruymen / Getty Images The Me, Myself, And Irene co-stars dated for a year and a half and were even engaged back in 2000. 16. Keira Knightly and Jamie Dornan Evan Agostini / Getty Images Back in 2003, before we knew Jamie Dornan as Mr Grey, he was a little-known actor and the long term boyfriend of Hollywood star Keira. 17. Ciara and Bow Wow Marsaili McGrath / Stringer Ciara's engagement to Russell Wilson isn't her first – back in 2006 she was engaged to Bow Wow. They were together for two years and even released a song together!