Top 10 Celebrities You Had No Idea Dated Each Other

#10: Demi Lovato & Ryan Phillippe

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Ryan Phillippe, best known for films like “Cruel Intentions” and “I Know What You Did Last Summer” and pop star Demi Lovato did not have the longest relationship. A good reason for why it didn’t last was probably because he was 36 and she was 18 when they began their love affair. Father of two with ex-wife Reese Witherspoon, Phillippe was also welcoming a third child with ex Alexis Knapp at the time. At her age, Demi was probably not ready to be a step mom to 3 kids. That being said, the relationship between the two was rumored to have been more physical than serious.

Former cyclist Lance Armstrong and 90s star and fashion designer Ashley Olsen hooked up back in 2007, but it was a short-lived romance. A considersble age gap of 15 years could have had a major impact for why things didn’t really work out for these two at the time. Photo evidence exists of the the two cuddling and kissing outside of a hotel on an early morning. Meanwhile, a book written by New York Times scribe Juliet Macur tells all on Armstrong’s rise to fame and his downfall, and it also addresses the quick romance between these two.

#8: Kim Kardashian & Nick Lachey

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98 Degrees front man Nick Lachey and reality TV personality Kim Kardashian got together back in 2006. Based on reports from Lachey himself, Kim appeared to be more concerned with increasing her popularity than with actually finding love. Lachey allegedly quipped: "We went to a movie. No one followed us there. Somehow, mysteriously, when we left, there were 30 photographers waiting outside." Soon after, Kim K. was spotted around town with none other than Nick Cannon, which we bet you didn’t know either!

Leonardo DiCaprio has become known over the years for his penchant for dating models, especially Victoria Secret models. This high profile actor is rumored to have dated over 10 angels! One in particular that stood out was his brief romance back in 1995 with London supermodel Naomi Campbell. Their relationship wasn’t a long lived affair, but the pair are said have had a pretty amicable breakup. In fact, they continue to have similar circles of friends. It just goes to show that not all Hollywood relationships have to end in a volatile way!

#6: Natalie Portman & Moby

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This relationship brought a lot of flack to Moby, who is best known for his electronic music career. When he and Natalie Portman got together, she was at the height of her “Star Wars” fame, so as you can probably imagine there were more than a few superfans eager to hate on their courtship. Moby received some backlash from the romance and was later quoted as saying, “You can’t date Luke Skywalker’s mom and not have them hate your guts.” The relationship may not have lasted, but it did happen!

Now that she’s married to Joe Manganiello, it’s hard to imagine her with anyone else! Sofia Vergara is best known for her character on the hit show “Modern Family”, but long before that, she actually dated the King of Latin Pop Enrique Iglesias. Not much is know about their relationship since it happened, for the most part, outside of the spotlight. Seems that these two just weren’t destined to end up together! Years later though, now that she is debatably more famous than he is, we wonder if they’re still in touch!

When these two got together, it was at the onset of both their careers. Timberlake was 16 and just getting started as the frontman for NSYNC and Fergie was 23, making music with her band Wild Orchid. Like many of the other couples on our list, we have to guess that the age gap played a part in this relationship’s demise. Deep down, JT must have known that he had an ever bigger romance lurking in the distance...we’re talking of course, about Britney Spears.

#3: Sandra Bullock & Ryan Gosling

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Despite being almost 16 years older than him, Academy Award winner Sandra Bullock dated Ryan Gosling after meeting him on the set of the 2002 thriller “Murder by Numbers”. The two dated between 2002 to 2003, and were seen publicly on a number of occasions. We get that that is a pretty big age gap, but can you blame Bullock for going after a guy like Gosling? Although their relationship didn’t last long, Gosling appeared to have done quite a number on the actress, with one source claiming that she was “brokenhearted” after the split.

#2: Cher & Tom Cruise

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Whenever you think of Cher, you likely think of “Sonny and Cher,” but this time we’re talking about her fling with “Mission Impossible” star Tom Cruise. The two dated back in the mid-‘80s 7 when he was just getting started in his acting career and she was already in the middle of hers. The two had supposedly met at a fundraising event at the White House and immediately hit it off. Despite being 16 years his senior, Cher didn’t hold back in a candid interview with Oprah later in life, when she remarked of Cruise that she was “crazy about him.” Before we unveil our top pick, here are a few honorable mentions: Helen Mirren & Liam Neeson Rashida Jones & Tobey Maguire Alanis Morissette & Ryan Reynolds

And coming in at number one are two musical artists who need no introduction. While it may seem hard to believe, Madonna and Tupac actually dated! These two were said to have dated three years prior to Tupac’s untimely death – so in 1993. Can you picture what the world would look like if these two had stayed together? We can only imagine what their kids would have been up to. It is really a shame it wasn’t meant to be, because we feel confident in saying they would have been their generations Jay-Z and Beyonce.