12 Celebrity Couples We Wish Still Made Headlines

56th Annual Primetime Emmy Awards - Arrivals

Celebrity couples failing in Hollywood is rather commonplace. Throughout the years we’ve seen relationships come and go with some of the biggest names in the business. However, there are some relationships that we will never forget even though they didn’t make it.

Since the beginning of time the public has always craved celebrity dating news. Unfortunately for the stars, we the public get a up-close-and-personal look at their private lives. Some people (and I’m not saying it’s me) get so attached to these relationships they have a hard time accepting the fact they are over.

We’ve compiled a collection of celebrity relationships that sadly didn’t make it, but we will never forget….

56th Annual Primetime Emmy Awards - Arrivals

Jennifer Aniston and Brad Pitt

Brad Pitt and Jennifer Aniston were one of the most popular couples in the history of Hollywood. The two met in 1998 and were married in private in Malibu two years later. Their marriage was considered pristine by all accounts in the celebrity world. However, in January 2005 they shocked the public by deciding to separate. Two months later Aniston filed for divorce citing irreconcilable differences. The two allegedly maintain a amicable relationship and check in on each other.

One of the most shocking breakups in Hollywood. Interestingly enough, Pitt’s relationship with Angelina Jolie started making news right around the time of their divorce.

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NBA All-Star Game

Britney Spears and Justin Timberlake

The two ‘Mickey Mouse Club’ all-stars began dating in early 1999.  Right around this time, both Timberlake and Spears’ careers took off. Spears doing solo work and Timberlake with N’Sync. Needless to say their relationship was as high-profile as it gets in Hollywood.

Unfortunately, their relationship only lasted a couple years as they broke up in 2002. This sent Spears on a downward spiral and adventure with Kevin Federline while Timberlake seemed to maintain himself pretty well after the relationship. He’s now found love with starlet Jessica Biel while Spears continues to be somewhat of a circus.

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The Twilight Saga: Breaking Dawn Part 1 - UK Premiere

Kristen Stewart and Robert Pattinson

The ‘Twilight’ romance was one of the most controversial breakups in recent memory. The two met on the set of ‘Twilight’ in 2008 and dated for about four years although it may have never been disclosed officially. The popularity of the film put the two right in the cross-hairs of the media.

The dream relationship came crashing down in 2012 when Stewart was photographed with director Rupert Sanders cheating on Pattinson. Recently the two have been linked together several times, but no one will forget the infidelity on Stewart’s behalf.

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Premiere Of Sony Pictures' "House Bunny" - Arrivals

Demi Moore and Bruce Willis/Ashton Kutcher

This is somewhat of a grand slam of celebrity couples we will not forget. First, you have Bruce Willis and Demi Moore. Moore married Willis in 1987 after two previous failed marriages. For a while many thought the couple was one of the more stable relationships in Hollywood. Together they have three children, but couldn’t make their marriage work long term. The two filed for divorce thirteen years later in 2000.

While Willis has been relatively quiet, Moore went on to date Ashton Kutcher in 2003. Kutcher is 15 years younger than Moore. The two were married in 2005. After six years the couple ended their marriage in 2011. Kutcher has gone on to date Mila Kunis while Moore, after four failed marriages, may be retired from that game.

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InStyle and Warner Bros. 68th Annual Golden Globe Awards Post-Party

Heidi Klum and Seal

In 2004, while pregnant with another man’s baby, Klum and Seal started dating. That same year after giving birth, Klum and Seal got engaged in British Columbia. The following year, 2005, Klum and Seal were married in Mexico. The two have three children together. Every year the couple renewed their wedding vows until the seventh year. That’s when they announced they were separating in 2012. The following year their divorce became official.

What makes this a little dodgey is that around the time of their divorce Klum was seen with bodyguard Martin Kristen in a rather compromising situation.

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The 55th Annual GRAMMY Awards - Backstage And Audience

Rihanna and Chris Brown

Perhaps the most notorious relationship on the entire list, Rihanna and Chris Brown are no longer together after Brown allegedly physically assaulted Rihanna. After dating for quiet some time, on February 8 2009, Rihanna’s performance at the 51st Grammy Awards was cancelled. Reports later surfaced that Brown had been arrested for assault and making criminal threats. TMZ somehow acquired pictures of Rihanna severely bruised following the incident.

While the couple has been in communication since the incident, Brown has been forever blacklisted in Hollywood.

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59th Annual Golden Globe Awards

Angelina Jolie and Billy Bob Thornton

Imagine going from Billy Bob Thornton to Brad Pitt… Just saying. After only two months of dating Jolie married Billy Bob Thornton in 2000 in Las Vegas. This was after a failed marriage to actor Johnny Lee Miller and a relationship with model Jenny Shimizu. The couple adopted a child from Cambodia, but was divorced by 2003. There relationship is most memorable for being weird. They carried viles of each other’s blood around their neck during their marriage.

As mentioned before, Jolie was highly scrutinized because of her connection with Brad Pitt during the shooting of ‘Mr. and Mrs. Smith’ in 2005 when Pitt was married to Aniston.

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2005 Teen Choice Awards - Show

Rachel McAdams and Ryan Gosling

Perhaps even more heart-breaking than Pattinson and Stewart was the break-up of ‘The Notebook’ stars Rachel McAdams and Ryan Gosling. While people fell in love with the movie the two fell in love around 2005 and dated for two years until breaking up. They briefly united in the Summer of 2008, but never made it work.

Both Gosling and McAdams have moved on. Gosling has been dating actress/model Eva Mendes since 2011. McAdams is currently single to our knowledge after a two-year relationship with actor Michael Sheen.

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2011 American Music Awards - Arrivals

Selena Gomez and Justin Bieber

The modern-day Timberlake and Spears, Justin Bieber and Selena Gomez started dating in December 2010. The two were photographed together on various vacations and confirmed their relationship at an Oscar’s party in 2011. The two ended their relationship after two years in November 2012 much to the delight of teeny-boppers all over the world. They tried to get back together, but never did make it.

Now, Gomez remains relatively quiet, while Bieber on the other hand… well, you know…

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Kim Kardashian And Kris Humphries Attend Their Divorce Hearing

Kim Kardashian and Kris Humphries

In May of 2011, Kim Kardashian got engaged to NBA basketball player Kris Humphries after over a year of dating. The two had an extremely extravagant wedding that proved to be all for nothing. After 72 days of marriage they filed for divorce citing irreconcilable differences. From that point forward there was a series of legal nonsense that went on between the two until their divorce was finally finalized this year.

This relationship will always go down in Hollywood history as one of the biggest jokes. We all know where Kardashian is now…

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2012 Vanity Fair Oscar Party Hosted By Graydon Carter - Arrivals

Katie Holmes and Tom Cruise

Katie Holmes and Scientologist (is that even what they’re called) Tom Cruise were probably one of the odder relationships in Hollywood history. Tom announced his love for Holmes by famously jumping on Oprah’s couch during live shooting. In 2006, they had a busy year. First they had their first child, Suri, and then they were married on November 18th. Close to six years later the two were divorced.

While the relationship came as a surprise to many after two fail marriages on Cruise’s behalf. I think most people were even more surprised to hear of their divorce. Since the divorce, both have kept a relatively low profile.

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13th Annual ESPY Awards - Arrivals

Jessica Simpson and Nick Lachey

Nick Lachey and Jessica Simpson are the founders of the reality TV couples show. Thus, one can also say they are the founders of the reality TV couples divorce trend. Pop stars Lachey and Simpson began dating in 1999 and were married in 2002. They were then featured on MTV’s ‘Newlyweds: Nick and Jessica’, which filmed the two in the early stages of their relationship. In 2005, it was announced that the couple was separating. Interestingly, Nick declined all divorce settlement offerings from Simpson because of her higher net worth. The divorce was finalized in 2006.

Since the end of their relationship they’ve both went on to find love. Lachey with MTV’s Vanessa Minnillo and Simpson with NFLer Eric Johnson. Both couples are currently married.

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