Anne Heche & Ellen DeGeneres
Ellen DeGeneres started her career as a comedian in the 1980s, but it wasn’t until 1997 that she came out as a lesbian. As soon as she came out, she also revealed she was dating actress Anne Heche.
The two enjoyed a very happy relationship until their breakup in 2000. It turns out that Anne hooked up with Ellen’s cameraman and later had his baby. Their drama-filled breakup made headlines everywhere.
Naya Rivera & Big Sean
This wasn’t so long ago, but it feels like it happened in another lifetime. Back when Glee was still on the air, Naya Rivera was dating rapper Big Sean, and the two eventually got engaged.
However, Sean broke her heart when he decided that he didn’t want to date her anymore and started going out with Ariana Grande instead. Breaking up with someone isn’t a crime, but the problem was that he didn’t actually tell Rivera, and she found out about their breakup on the internet. Ouch.
Alanis Morissette & Ryan Reynolds
One huge celebrity couple that people seem to forget about is Alanis Morissette and Ryan Reynolds. The Canadian power couple were together for four years and were even engaged, but sadly, they never walked down the aisle.
They never revealed the cause of their breakup, but Morissette hinted that it was Reynolds who wanted to end it. He moved on pretty quickly, but she had a very hard time getting over their breakup.
Britney Spears & Colin Farrell
This bizarre couple split up almost as fast as they got together. People were shocked when Colin Farrell brought pop princess Britney Spears to the premiere of his movie, The Recruit, in 2003. That was about the only time they were in public together.
Their romance was allegedly kind of chaotic, given that Farrell was a notorious bad boy and Spears was slowly breaking out of her girl-next-door image. They had a passionate fling, and then they quickly went their separate ways.
Madonna & Michael Jackson
Back in the day, it was rumored that Madonna and Michael Jackson were dating, but the two kept quiet, and the rumors eventually faded away. Flash forward to 2016, and Madonna is actually confirming that the rumors were true.
The two pop giants dated very briefly in 1991 but kept it a secret. According to Madonna, he was too shy for her, and she was too intense. However, they remained good friends after their breakup, however.
Alexis Bledel & Milo Ventimiglia
Back when Gilmore Girls was still on the air, it was a huge deal for fans all over the world to learn that stars Alexis Bledel and Milo Ventimiglia were not only dating on-screen but also in real life.
The adorable couple made many public appearances together and enjoyed each other’s company for three years before they went their separate ways. It’s interesting to know that all that on-screen chemistry wasn’t faked.
Kim Kardashian & Nick Cannon
Before her infamous sex tape, Kim Kardashian was, at best, some kind of D-list celebrity. She hung out with Paris Hilton and went out with none other than Nick Cannon.
Their romance was very brief, allegedly because when her sex tape was released, Cannon wanted nothing to do with it, so he pulled the plug on their relationship. He went on to marry Mariah Carey, and Kim went on to become one of the biggest reality TV stars ever.
Drew Barrymore & David Arquette
Drew Barrymore and David Arquette were one of the cutest couples from the 1990s. The two met on the set of Never Been Kissed, where they played siblings. From then on, the two were inseparable.
Although the pictures of them together are very clear, Barrymore always denied they were dating. We are not sure why, because it’s obvious, and also because Arquette admitted they did date. Maybe the breakup was too painful for her?
January Jones & Ashton Kutcher
January Jones and Ashton Kutcher met when they were both struggling actors, and they even shared an apartment in Los Angeles for some time. They were very happy together until Kutcher began gaining recognition.
When he got the role of Kelso in That 70’s Show, Kutcher was put on the map, and according to Jones, his ego started to grow bigger and bigger. Shortly after that, the pair split up, and they both moved on to bigger and better things.
Michael Keaton & Courteney Cox
Michael Keaton and Courteney Cox dated long before she starred in Friends. The two were in a very serious relationship for over five years, and although they were very in love with each other, it didn’t seem to be going anywhere.
When asked about the relationship, Cox said: > “It’s the most important relationship I’ve ever had, and he is the most wonderful person I’ve ever met.” > It sounds like she loved him very much, but sadly, the relationship ended in 1995.
Seal & Tyra Banks
Singer Seal seems to have a thing for supermodels –or supermodels seem to have a thing for Seal. Either way, before marrying Heidi Klum, Seal briefly dated her fellow supermodel, Tyra Banks.
Although they were spotted in public a few times, the two kept their relationship very private, so we don’t know much about it. However, we can surely say it was very brief, and the two quickly moved on.
Jennifer Aniston & Paul Rudd
One of the most forgotten Hollywood relationships is definitely this one. But it’s true, Jennifer Aniston and Paul Rudd dated in 1998. The two met on the set of The Object of My Affection and immediately developed feelings for each other.
Their romance was very brief, but luckily it ended on good terms. The two reunited on the set of Friends a couple of years later, where he played Mike Hannigan, and they also worked on a couple of other projects together.
Kiefer Sutherland & Julia Roberts
The relationship between Kiefer Sutherland and Julia Roberts was bizarre and filled with drama from the start. Sutherland left his then-wife to date Roberts when they met on the set of a movie, and their relationship was very intense.
They got engaged super fast and wasted no time planning the wedding. But just a few days before the big day, rumors that Sutherland cheated on Roberts with a stripper started flying around, and Roberts called the wedding off. Their relationship was super dramatic, yet we all kind of forgot that it happened.
Owen Wilson & Sheryl Crow
You probably didn’t know about this one, but actor Owen Wilson and singer Sheryl Crow were an item for three years. The two were happy for a while, but according to Crow, fame got in the way.
In an interview, she talked about the struggles of celebrities dating each other. There’s a lot of competition between these couples, and one may get jealous of the other’s fame, which is what Crow admitted to.
Selena Gomez & Nick Jonas
This one was just a rumor for many years until Nick Jonas himself confirmed it only a few months ago. The truth is that Selena Gomez and the young musician had a short-lived romance after he ended his relationship with Miley Cyrus.
Not much is known about why they broke up. The two have kept it extremely private, which is surprising considering that they both have had highly public relationships with other people.
Michelle Rodriguez & Cara Delevingne
Michelle Rodriguez and Cara Delevigne made headlines when they started showing extreme displays of affection on a boat, during a basketball game, and basically anywhere they could. But when a fling starts out in a very intense way, it usually also ends that way.
They reportedly had a messy breakup that left both of them heartbroken. Although they were never officially a couple, they were very invested in their relationship. They quickly moved on, however, so it probably wasn’t that bad.
Ryan Gosling & Sandra Bullock
Ryan Gosling and Sandra Bullock had one of the cutest Hollywood relationships of all time. Not only were they all smiles when they were around each other, but you could feel their chemistry through the screen.
Surprisingly, their relationship lasted less than a year. Their breakup was very amicable, and the two only have good things to say about each other. In fact, Gosling referred to Bullock and his other ex, Rachel McAdams, as “two of the greatest girlfriends of all time.”
Tom Cruise & Cher
And the award for the most bizarre relationship ever goes to… Tom Cruise and Cher! Nobody knows how or why it happened, but it is a fact that it wasn’t a crazy fever dream.It was very real.
The two dated briefly in the 1980s but remained friendly after their breakup. In fact, they were spotted together several times over the years.
Edward Norton & Courtney Love
Edward Norton and Courtney Love actually dated for three years. The couple met while filming The People vs. Larry Flynt and became infatuated with each other soon after.
However, their breakup was nothing but sour. Although we don’t know exactly why they broke up, all we know is that it was messy. Love even called Norton out on Twitter, where she claimed he owes her $300,000.
Rihanna & Shia LaBeouf
Rihanna and Shia LaBeouf had a very short-lived thing. In fact, they hooked up only once, but that’s enough for the whole world to be shocked at this odd pair.
The two hooked up in 2007, according to LaBeouf, but there just wasn’t a spark, and they parted ways. He even claimed they are still friends. It is very clear that there was absolutely no chemistry there.
Danny Wood & Halle Berry
Halle Berry was just a beauty queen and a struggling actress when she started dating Danny Wood, a member of New Kids on the Block. Back then, he was the superstar, and she was a nobody. Oh, how the tables have turned.
The two enjoyed a very low-key romance until Berry started gaining recognition. Allegedly, Wood couldn’t handle the fact that Berry was becoming more successful while his star power faded away, so the two split up.
Robert Downey Jr. & Sarah Jessica Parker
You might not believe this, but Robert Downey Jr. and Sarah Jessica Parker were one of the hottest couples around during the 1980s. In fact, the two had a very long relationship that went on for seven years.
However, their breakup was a sad one, however. They loved each other very much, but Downey’s struggle with addiction got in the way of their relationship, to the point where Parker couldn’t handle it anymore. The two reportedly reunited several years later when Downey got clean, and they got some friendly closure.
Janet Jackson & Matthew McConaughey
Janet Jackson and Matthew McConaughey were photographed at the Grammys right when they first met, and they seemed to really hit it off. Soon after, rumors went around that the two exchanged numbers right there and started dating.
After more than a decade, McConaughey finally admitted that the rumors had been confirmed but that they only went out a couple of times. We don’t know how much of that is true, but both moved on a long time ago.
Patrick Wilson & Jennifer Love Hewitt
Jennifer Love Hewitt and Patrick Wilson met in 2001 when she saw a production of The Full Monty that he was in. However, Hewitt was dating singer Rich Cronin at the time and decided to leave him for Wilson.
The couple quickly began making appearances on red carpets and posed for paparazzi pictures together. But, although they seemed to be crazy about each other, they spent less than a year together.
Liev Schreiber & Kristin Davis
Kristin Davis was at the height of her career thanks to the success of Sex and the City when she started dating Liev Schreiber in 2003. The two were really cute together, but it didn’t last very long.
In fact, the whole thing ended when Schreiber met his long-time love, Naomi Watts, who he dated for 11 years.
Moby & Natalie Portman
Moby and Natalie Portman allegedly dated for a while a long time ago – at least, according to Moby. He has maintained for many years that it was true, while Portman has denied it all this time.
In his defense, Moby said that dating Portman actually caused Star Wars fans to hate him, so why would he lie about it? Although there are pictures of them together, they aren’t doing anything romantic in them, so we’ll never know the truth.
Ryan Phillippe & Demi Lovato
Ryan Phillippe‘s relationship with the mother of two of his children, Reese Witherspoon, infamously ended when he allegedly cheated on her. Flash forward to a couple of years ago, and he started dating Demi Lovato.
His relationship with Lovato allegedly ended when she found out he was having a baby with his ex, Alexis Knapp. Demi didn’t hesitate to dump him, having realized he hadn’t changed a single bit.
Kaley Cuoco & Henry Cavill
Everyone was shocked when Henry Cavill appeared hand-in-hand in front of the paparazzi with Kaley Cuoco. The whole thing was very sudden, and it ended as quickly as it started, which spawned rumors that it was actually a fake relationship.
The two were photographed every single day for a week, and then, all of a sudden, they broke up. Also, the two shared a PR team, which made the whole thing even more suspicious. Either way, it happened, and everyone forgot about it.
Lance Armstrong & Kate Hudson
Not many people remember that Lance Armstrong and Kate Hudson dated, but it’s true. The two got together in 2008, and their relationship moved on very fast – in fact, too fast for Armstrong.
Allegedly, the relationship was getting more and more serious, and Armstrong felt a little suffocated by her, so he broke it off. As it turns out, it was Hudson who dodged a bullet since it was discovered that the cyclist had been doping for years and was stripped of all his medals.
JC Chasez & Eva Longoria
Back when NSYNC was huge, JC Chasez dated Eva Longoria, who was still getting her name out in Hollywood. The two shared a private relationship but still went to many red carpets together.
We don’t know exactly what happened between the two, but allegedly, Longoria inspired many of Chasez’s solo songs, especially the sad ones. Hopefully, he’s gotten over it by now, although getting over Eva Longoria must be very difficult.
Kristen Johnson & Ryan Reynolds
Our first repeat offender is here. Ryan Reynolds dated Kristen Johnson for a year before calling it quits. In fact, this is the only time they were photographed together: the premiere of the 1999 film The Green Mile.
This serial dater couldn’t wait to move on to the next one and started dating Alanis Morissette not long after their breakup. We don’t know exactly why they broke up, but they didn’t seem very crazy about each other in the first place.
Leonardo DiCaprio & Blake Lively
Leonardo DiCaprio has been linked to over 50 women, and it seems like he will never settle down. However, when he dated Blake Lively, people had a feeling that these two were serious.
They were spotted vacationing in the French Riviera and in Italy and were also seen having fun at Disneyland. However, Lively wanted something serious, while DiCaprio didn’t, so they broke up.
Sheryl Crow & Josh Charles
Sheryl Crow briefly dated The Good Wife actor Josh Charles in 2003. The two seemed to be getting serious when she brought him to the Grammys as her date, but that was far from the truth.
Allegedly, she gave it a try but quickly realized that they weren’t made for each other. She was looking for someone to marry and have kids with, and Charles just wasn’t it. She later married Lance Armstrong.
Josh Groban & January Jones
This relationship kind of went under the radar, but the truth is that Josh Groban and January Jones were very much in love and dated for almost two years. They were also not private about it and appeared together in public numerous times.
Despite their love for each other, their relationship ended. According to Groban, however, they are still very close friends and love each other very much. He also revealed that it was his longest relationship to date.
50 Cent & Chelsea Handler
50 Cent and Chelsea Handler shocked the world when they started dating, but the public soon realized that they were a super cute couple. The relationship didn’t even last half a year, but the two remained very close.
In fact, the rapper appeared on her former late-night show and also on her current show. The exes talked and joked about their former relationship and even discussed the possibility of hooking up again.
Johnny Depp & Ellen Barkin
Johnny Depp broke hearts left and right in the 1990s, and Ellen Barkin was one of his many victims. The two started dating in 1994 and had a very intense but also brief romance. However, Depp’s bad boy ways got in the middle of their relationship.
Another problem was the fact that they got together shortly after Depp had broken up with Winona Ryder, to whom he had been engaged. It seems as if Barkin was just a rebound.
Christina Applegate & Brad Pitt
Probably the best-looking couple to ever exist, Christina Applegate and Brad Pitt dated briefly in 1989. Back then, she was the big star, and he only had a couple of small roles on TV. Their breakup was extremely interesting.
Applegate brought him to the MTV Movie Awards in 1989 as her date. However, during the show, she met Skid Row singer Sebastian Bach and reportedly dumped Pitt right then and there. If Brad Pitt can get dumped just like that, there’s no hope for us.chr