From time to time, celebrities cross paths and find love in unexpected places. Imagine spending hours upon hours on set with a young Ryan Gosling, a fling is essentially unavoidable, even if you may not be the best match, because, well, it’s Ryan freaking Gosling.
For many young actors and singers on the brink of success in their careers, various romances bloomed, and then, often fizzled. Age is only a number when it comes to love in Hollywood, bringing together surprising pairs like Fergie and Justin Timberlake, and Tom Cruise and Cher.
Whether or not it was meant to be, sparks flew at one point or another between celebrities you could never imagine dating. Keep reading to find out who Kim Kardashian dated pre-Kanye West, and what rumored engagement with Johnny Depp ended in 1989.
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1. Ryan Reynolds and Alanis Morrisette
Reynolds and Morisette dated for four and a half years before breaking off their engagement in 2007.
2. Sandra Bullock and Ryan Gosling
Even though Bullock had 16 years on Gosling, they dated for a year. Gosling told the U.K.'s The Times that Bullock was one of his greatest girlfriends ever.
3. Johnny Depp and Jennifer Grey
Rumors flew that Depp was engaged to this Dirty Dancing star in 1989.
4. Matthew McConaughey and Janet Jackson
After they met at the Grammys in 2002, word spread about a brief fling, but McConaughey claims they were "just friends".
5. Sofia Vergara and Enrique Iglesias
The couple allegedly dated back in the '90s!
6. Nick Lachey and Kim Kardashian
Their relationship didn't last long even though photographers "mysteriously" showed up anywhere they went during the time they were together.
7. Nick Cannon and Kim Kardashian
After Lachey, Kim Kardashian moved on to Cannon. Unfortunately their flame didn't last very long either before they parted ways.
8. Sheryl Crow and Owen Wilson
Pre-Lance Armstrong, Crow dated Wilson and they remain good friends today. She dedicated her song Safe And Sound to Wilson in 2002.
9. Justin Timberlake and Fergie
The relationship was short-lived, perhaps because Timberlake was only 16 and Fergie was 23 at the time.
10. Matthew Morrison and Kristen Bell
Bell told Us magazine that she "went to college with Matty Morrison…We actually dated very briefly, so I'll have to say maybe Matt Morrison is my favorite part of Glee for various reasons."
11. Christian Bale and Drew Barrymore
Barrymore and Bale went on a date as teens, but according to Bale, the date did not go well. He told GQ Australia: “We went to see some bloody awful horror film, and that was the end of it. She never called again.”
12. Tom Cruise and Cher
In a 2013 interview with Andy Cohen, Cher talked about her relationship with much younger Cruise in the '80s, describing him as a "great, lovable guy" and their relationship as "hot and heavy".
13. Will Smith and Tyra Banks
Sparks apparently flew after Banks guest-starred on The Fresh Prince of Bel-Air.
14. George Clooney and Kelly Preston
Before meeting John Travolta, Preston lived with Clooney in 1988. They even had a pet pig together.
15. Gwyneth Paltrow and Brad Pitt
After dating for three years in the '90s, Paltrow and Pitt were set to get married until Paltrow called off the engagement.
16. Hilary Duff and Shia LaBeouf
After one horrible date together, these two called it quits!
17. Robert Downey Jr. and Sarah Jessica Parker
These two dated for seven whole years in the '80s, but his alcohol and drug abuse put a strain on the relationship.
18. Teri Hatcher and Michael Bolton
Before Bolton's engagement to Hatcher's Desperate Housewives co-star Nicollette Sheridan, Hatcher and Bolton hit it off after she starred in his music video in the '90s.
19. Aaron Carter and Lindsay Lohan
Carter allegedly got between Lohan and Hilary Duff, starting a duel between the two actresses. Carter explained on The Big Idea, “I started dating Hilary [Duff] on my 13th birthday. I was dating her for like a year and a half and then I just got a little bored so I went and I started getting to know Lindsay [Lohan], dating Lindsay.”
20. Brooke Shields and Nicolas Cage
The pair first appeared together at the premiere of Cage's film Moonstruck in 1987. A year later, they called it quits.
