15 Celebs You Didn't Know Were Once Lovers

There are some couples in Hollywood that just make such a perfect pair that you can’t imagine it any other way.

We are so used to some celebrities being in the spotlight and making their lives as public as possible that we feel like we should know everything about them. It happens so often that we are shocked when we find out two celebrities are dating or have dated in the past and we had no idea. Yes, it’s true, there are celebrities out there that value their privacy and want to keep their love lives out of the public eye. We try to respect that even though we love finding out who is dating who and whether they will be able to survive the Hollywood curse that seems to befall so many relationships.

There are some couples in Hollywood that just make such a perfect pair that you can’t imagine it any other way. Ben Affleck and Jennifer Garner are a good example and so were Angelina Jolie and Brad Pitt even though both those couples have separated now. These days, however, the relationships in Hollywood aren’t really built to last.

There are some Hollywood couples however that would come as a shock to you. They either started and were over and done before we knew it or they were so bizarre that we couldn’t imagine how they got together in the first place. If it weren’t for the media, we may never know about these crazy pairings. You are truly in for a treat when it comes to this celebrity list; below are 15 celebrities you had no idea were ever lovers!

15 Justin Timberlake and Fergie

Shocked? A little bit, I have to say. It’s not surprising of course that singers get together especially when they have something major in common. After all, Justin did date Britney at one point. But it’s just really hard to imagine him with Fergie. She seems like the kind of girl that would eat him whole. Of course, they dated in the 90’s before they were as famous as they are now, so their relationship was a little more under the radar. She was also cradle robbing hardcore with almost a decade on Justin when he was a mere sixteen years old. Considering the huge age gap, there’s a really good chance that she taught the young lad everything he knows in the bedroom. Say thank you, Britney! The relationship didn’t last very long however which is probably why we never heard much about it.

14 Shia LaBeouf and Rihanna

Yup, this actually happened. I know, it’s beyond incomprehensible. What would they have in common? What would they talk about? Shia is so political and at times not on the same planet as the rest of us while Rihanna is into champagne and diamonds. Maybe it’s because Shia is in the media often for a lot of crazy behavior. We aren’t sure how long the relationship lasted as it seemed to be just a flicker before the flame went out. When questioned about it, they claimed it was just a date or two, but it’s confusing as to how it happened in the first place. What if they would have fallen in love, could you even imagine it? They just seem such complete opposites that you couldn’t imagine it ever working long term.

13 Natalie Portman and Moby

It’s hard to imagine these two together, but they dated for a period of time in 2001. Everyone thought they were the most unlikely couple of all time. She was a classic beauty while he seemed to be a big nerd. Even though the two of them were happy, he got a lot of flack for dating the Star Wars star. She had developed such a cult following that they were outraged when he started dating her. Even the nerds didn’t like that he got an in. She was supposed to be sacred and untouchable forever. “As far as the very brief affair that I had with Natalie, it’s made me a target of a lot of nerd wrath. You don’t date Luke Skywalker’s mom and not have them hate your guts.” It’s hilarious how people take it so personally when they don’t actually know the celebrity.

12 Kim Kardashian and Nick Lachey

At this point it’s hard to picture anyone with Kim besides Kanye, they seem like a match made in heaven. But there was a time where Kim dated Nick Lachey. Certainly surprising because you would think that she would not be his type at all. They weren’t together more than a few dates and Nick accused her of using him to get famous. It was shortly after his divorce from Jessica Simpson, and he said he spent a week with Kim and was sure that she called the paparazzi every time they went out. He was asked in Details whether their first date marked the moment she started getting noticed in the media and he responded with, “That’s one way to interpret it. Let’s just say this: We went to a movie. No one followed us there. Somehow, mysteriously, when we left, there were 30 photographers waiting outside,” he said, laughing.

11 Drew Barrymore and David Arquette

I can almost see this one going down because the two are both very quirky people. I’ve always thought he was a weird looking human but Drew seemed to like dating weird looking humans. The two dated when they were just teenagers, long before he was with Friends star Courteney Cox. He was nineteen and Drew was only sixteen at the time. It was a romance that didn’t last very long, but the two stayed in contact and co-starred together in Never Been Kissed as well as Scream. “Drew and I used to date when we were very young kids. Well, not little kids. She's just one of the sweetest, kindest people in Hollywood. She always has been, and she always will be. She's just a lovely, sweet person. We used to run around and just be silly.” David, of course, went on to date his former wife Courteney Cox and well the rest is history.

10 Ashley Olsen and Lance Armstrong

You would think there would be no more unlikely pair than the fashionista Ashley Olsen and Lance Armstrong. They had what could only be called a fling in 2007. They were caught kissing outside of a hotel early in the morning, but there wasn’t much heard of them together after that. They did have a fifteen-year age difference between them, so it’s hard to say why things fizzled between them. When asked once about the affair Lance said that “his people” told him to break things off with Ashley. Apparently, they worried that the romance would hurt the image that he had at the time as an athlete and an all-around good guy. It wasn’t his career that they were so much worried about but his cancer work. Korioth told Lance at the time, “Whoa, dude, bad idea. You’ve got to put a stop to this right now.” Lance didn’t take it well and responded with a typical, “She’s twenty-one… F**k you.” At the end of the day they did split up shortly after that, so maybe he folded under pressure.

9 Channing Tatum and Amanda Bynes

We know Channing Tatum as the 21 Jump Street and Magic Mike star and man about Hollywood. He certainly has made a decent career for himself these days and has a little more freedom in the movies that he gets to work in. He’s been with his now wife for years and has a few children. His wife is so gorgeous that it’s hard to believe that he was ever with anyone else. Not only is she stunning but she has that dancer’s body! Back before he was married however it turned out that he dated Amanda Bynes. She now seems to have gone off the crazy train, but back in the day, she was pumping out a lot of the teen rom-coms. The two were linked together while they were filming She’s the Man. The two of them looked absolutely adorable together but alas it wasn’t meant to be. These days the two are still in contact as Tatum does follow her on Twitter.

8 Matthew Perry and Heather Graham

The two seem like an odd pair, but Matthew has always been a handsome man and what girl could resist that sense of humor? I would take a funny man over anything else, any day of the week. There is just something about a guy that can make you laugh. The two were rumored to be together in 2003 for a brief fling, the media called it a hookup, but it may have been a little more than that. It’s unclear whether they were dating or just fooling around because it was over before it really got going. They never went public, so there was always rumors flying about what happened to them. They could have been an adorable couple, but in the end, it didn’t work out. Aside from that Heather Graham has been away from Hollywood for some time.

7 Blake Lively and Leonardo DiCaprio

Leonardo DiCaprio has always been known to date Victoria’s Secret models; it’s pretty much his MO. It’s surprising ever to see him dating an actress, but there have been a few rare occasions when he has. Long before Deadpool came into the picture, Blake Lively was linked to Leonardo DiCaprio. The two were seen multiple times throughout Europe. They hung out at Cannes, and it seemed like Leonardo had really fallen for the girl. It’s rare that you see Leonardo holding hands with anyone, but he was seen strolling through Europe hand in hand with Blake. The love affair came to an abrupt stop, however, and no one really knew why they decided to stop seeing each other. Leo went back to dating models, and Blake met and married her now-husband Ryan Reynolds. It’s too bad because I thought they made a pretty cute couple.

6 Ryan Gosling and Sandra Bullock

Ryan Gosling has always seemed like a great guy to date, he’s always super attentive to his girlfriends, and the speech he made to his wife Eva Mendes at the Golden Globes was awe inspiring. I know it made women all over the world swoon. Before he settled down, however, he had a brief romance with Sandra Bullock whom he met on the set of Murder by Numbers. Despite the fact that there is a sixteen-year age difference between the two they started up a steamy romance. It wasn’t just a fling either; she was his girlfriend for a year before they broke up. Ryan seemed quite smitten with the actress, and they were often seen on the red carpet together. They didn’t seem fazed at all by the age difference, but when it ended, they stayed on good terms. Ryan has always called her one of “the greatest girlfriends of all time.” After that, he moved on to his next girlfriend Rachel McAdams who also made the great girlfriend list.

5 Naomi Campbell and Leonardo DiCaprio

It’s hard to believe that these two would ever have dated considering her reputation for drama and screaming matches with other celebrities. Especially since he is such a laid back actor, it’s really shocking the two would have started to date. He is well-known for dating models however, and in this case, when he started to date Naomi in 1995 she would have been one of many Victoria’s Secret models that he dated. He was quite young when they got together; it was just before he got the role in the blockbuster movie Titanic. The two were seen on his yacht a few years ago, and it was clear that they weren’t getting back together as the guy could not have looked more bored even though she was standing half naked in front of him in a bikini. The two have always remained friends, though, and Leonardo moved onto many more models after that.

4 Keira Knightley and Jamie Dornan

Every time I see Jamie Dornan I think of Fifty Shades of Grey. That’s what he’s most known for anyways, despite the fact that he’s been in other things. There was a time back when he wasn’t famous that he dated Keira Knightley. At the time she was a pretty big star while he was working as a Calvin Klein model. They did date for a few years, which is pretty long in Hollywood before they broke up. They were the kind of couple that drew stares all the time; they were gorgeous together. Jamie has often said that dating the famous actor prepared him for his own fame, which he is certainly dealing with now. They must have had a pretty bad breakup because when they were seen at the Golden Globes in 2015, they wouldn’t even look at one another. I don’t think he’s complaining these days however with all the attention he’s getting.

3 Vanessa Hudgens and Josh Hutcherson

We are so used to Vanessa Hudgens dating Zac Efron that it’s hard to believe she had time for anyone else. But the two did get together for a short time while they were filming Journey 2: Mysterious Island. It was the part two version of Journey to the Centre of the Earth starring The Rock. The two were just young when they got together and played love interests in the film. It’s not surprising that they started seeing one another. Their love affair, however, didn’t last any longer than filming did which made promoting the film very awkward, “We were [dating] at one point, but she broke my heart. No, I’m just kidding, that was a while ago, we’re really good friends now.” Something tells me he wasn’t kidding. However, there doesn’t seem to be any bad blood between them.

2 January Jones and Ashton Kutcher

Ashton Kutcher hooked up for a time with January Jones long before he was famous. At the time he was starring in movies like Dude Where’s My Car? and it was long before he was dating either of his future wives. They dated for years before breaking up in 2001 and from what January Jones had to say he was a terrible boyfriend. He used to tell her to give up her dream as an actress because he didn’t believe she would be good at it. It seemed like an extreme thing to say to someone considering he wasn’t exactly making blockbusters at the time either. She ended up proving him wrong however when she landed her role in the highly acclaimed TV show Mad Men. It makes you wonder how supportive he is when it came to Demi Moore’s career as well as his new wife’s Mila Kunis.

1 Tom Cruise and Cher

Talk about a mismatched couple; I find it hard to believe that the two would have anything in common. He seems so secretive especially when it comes to his religious life, and she is someone who is really “out there,” and doesn’t care about what she says and does. They had dated in 1987 long before he had the career that he does now, though she was going strong with her singing career. She described him as shy but said she was crazy about him. In fact, she was so crazy about him that she told people that he was one of the best lovers she’s ever had. “I had just the greatest lovers ever. Not a long list. It's just a good list.” She listed Tom as one of her top five best lovers ever. Despite their sixteen-year age gap, the two were together for more than just a summer fling. They broke up, and he eventually met his first wife, Mimi Rogers.



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15 Celebs You Didn't Know Were Once Lovers