From Happily Ever After To Never After: The Shortest Celebrity Relationships Ever

Just when you think that you have met your soulmate and have finally settled down, things can start to go downhill really fast. That’s exactly what happened to these celebrities. They believed that they found their soulmate, and then the relationship screeched to a halt. Some of them ended in weeks, and some in just a day! The following celebs had the shortest relationships in Hollywood.

Fred Armisen and Elisabeth Moss

People who work in the same industry seem to gravitate towards each other. This especially occurs in Hollywood. Two lovebirds end up getting together and everything seems to go great, especially when they are in the same or similar field. They have the career that they want, and now they have the mate that they desire.

Fred Armisen and Elisabeth Moss

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Such was the case with Fred Armisen and Elisabeth Moss. They were two thespians who seemed to have it together, except in their relationship. Their marriage lasted only eight months. Elisabeth has gone on record as saying, about the marriage, “It was extremely traumatic and awful and horrible.” Fred admitted to shock jock Howard Stern in an interview about his marriage to Elisabeth, saying “I think I was a terrible husband.”

Drew Barrymore and Tom Green

Some people have mixed feelings when they enter a relationship. One minute the relationship is going well, and then it rapidly goes downhill, and then back uphill again. Some relationships like this can end amicably, and such was the case with Drew Barrymore and Tom Green.

Drew Barrymore and Tom Green

The marriage between Drew Barrymore and Tom Green lasted for nine months. That’s really not all that bad, especially compared to other individuals in this article that you will see coming up. Not much is known about why their marriage did not last. Drew has gone on the record to say: “He has been a great friend and that won’t change.” Tom, in turn, has publicly stated: “Drew is a wonderful woman, I love her very much. I wish our marriage could have worked out; I wish her much happiness.”

Chad Michael Murray and Sophia Bush

Chad Michael Murray and Sophia Bush slipped and fell in love while working together on One Tree Hill. Chad and Sophia actually dated for two years before taking the big step towards marriage.

Chad Michael Murray and Sophia Bush

According to Daily Mail, during their marriage which only lasted for five months, Sophia believed that Chad was cheating on her with none other than Hilton heiress Paris Hilton. Sophia went on to give an interview when she made an appearance on Watch What Happens Live. She said in the appearance, “We were two stupid kids who had no business being in a relationship in the first place.” Sophia used fraud as a basis for her divorce.

Nicolas Cage and Lisa Marie Presley

Nicolas Cage got in pretty good with Lisa Marie Presley… at first. They met in 2000 at Johnny Ramone’s birthday bash where Nicolas Cage told Lisa about his love for Elvis Presley. What a way to rack up points, especially with the King of Rock and Roll’s daughter. Would that make Lisa Marie Presley a princess?

Nicolas Cage and Lisa Marie Presley

After two years of dating, Nicolas and Lisa Marie got married in Hawaii in August of 2002. All went well for a little while, and that is putting it lightly. They were married for only three months. Nicolas Cage filed for a divorce in November of 2002 and went on to say that they “shouldn’t have been married in the first place.”

Kid Rock and Pamela Anderson

Pamela Anderson certainly has a thing for rockers. She had Dr. Feelgood, I mean Tommy Lee, as a hubby before going to the cowboy, Kid Rock. They certainly seemed to be a picture-perfect couple.

Kid Rock and Pamela Anderson

Pamela Anderson knew plenty of guys in the rock scene but it was Kid Rock who she chose to marry. After dating for a short period of time, Kid Rock and Pamela Anderson ended up getting married in July of 2006 in St. Tropez on a yacht. Their marriage only lasted four months. Pamela Anderson would take to her personal blog to sum up her lack of wedded bliss: “It wasn’t a happy Thanksgiving.” There here was no more cowboy in her life for a while after their divorce.

Renée Zellweger and Kenny Chesney

Actress Renée Zellweger and country singer Kenny Chesney tied the knot on May 9, 2005, after dating for only four months. They had their wedding on St. John, Virgin Islands. With such a short dating period and then getting married, we might expect them to at least give the marriage some time, but that would not be the case.

Renée Zellweger and Kenny Chesney

After four months of marriage, Zellweger filed for divorce, citing “fraud” as the reason for their divorce. Zellweger would later dish about her marriage to Kenny Chesney in an interview with Now magazine. “I made the biggest personal mistake of my life. I felt a fool,” she declared.

Colin Farrell and Amelia Warner

Here we go with another unlucky four months of being together. This relationship has somewhat of a twist. Colin Farrell and Amelia Warner dated but never really got married, despite the fact that there was definitely a ceremony on a beach and reporters were quick to speculate on the future of this couple’s wedded bliss.

Colin Farrell and Amelia Warner

Farrel and Warner were in Tahiti when the “ceremony” took place but it was soon discovered that the entire event was legal. Amelia Warner told The Sun that the ceremony was more like a holiday than a marriage ceremony. The couple split just four months into their new life together.

Pamela Anderson and Rick Salomon

Pam Anderson had gone from rock and roll guys to dating a professional poker player when she met Rick Salomon. She has made this list twice and she is on a roll when it comes to relationships that do not last long. What is happening with Pamela Anderson and these guys?

Pamela Anderson and Rick Salomon

Pamela Anderson had actually known Rick Salomon for twenty years when they decided to get together. They even had “relations” of the behind closed doors kind for many years. This seems like it was getting off to a bad start already. They ended up getting married and the marriage lasted 69 days. When the couple got quickly divorced they cited fraud as the reason for the quick dissolution of their rocky marriage.

Jim Carrey and Lauren Holly

Jim Carrey and Lauren Holly were a couple for quite some time. These two were really in love with each other according to many Hollywood insiders. In fact, if you asked their closest friends at the time, they all thought that both Jim Carrey and Lauren Holly would be together forever. This was at a time before he started releasing viral videos that declared his love for Emma Stone.

Jim Carrey and Lauren Holly

These two seemed to have it all and when they finally tied the knot it seemed like they were going to spend the rest of their lives together in happiness. The marriage lasted only 10 months, and after they filed for divorce, they were reportedly still seeing each other on and off, but nothing came of this situation. Sometimes it’s just hard to let go of the people we love.

Bradley Cooper and Jennifer Esposito

Some folks get all excited about the prospect of getting married. Some people fall in love so deeply that they make decisions that they will regret. Bradley Cooper and Jennifer Esposito more than likely fell in love and rushed into their very short marriage.

Bradley Cooper and Jennifer Esposito

Bradley Cooper went on to tell Howard Stern in an interview, “It was just something that happened. The good thing is, we both realized it. . . . Sometimes you just realize it. It just wasn’t right. It’s interesting. . . . Things happen!” He also went on to tell US Weekly: “It was just something that happened.” Bradley and Jennifer’s marriage lasted only four months.

Kim Kardashian and Kris Humphries

Kim Kardashian once went out with Kris Humphries. They shacked up and then then married in front of a TV crew. Kim at the time was known for loving guys and leaving quickly leaving them. She had gone out with many men and even married some of them. Oftentimes, her selection of men left her critics scratching their heads. This was way before the queen of reality TV was married to Kanye West and started a family with him.

Kim Kardashian and Kris Humphries

The marriage between Kim K and Kris Humphries lasted only 72 days. Kris and Kim ended up getting divorced after landing $10 million for a wedding special. They both cited irreconcilable differences as the grounds for their divorce but it took months for Humphries to finally give Kardashian the dissolution of marriage she desperately wanted.

Charlie Sheen and Donna Peele

Charlie Sheen is well known for his multiple on-and-off-again relationships with women. He has probably had more women in one year than most men have had in a lifetime and that’s not even an exaggerated statement. Every time you looked up, Charlie Sheen had a different lady. He has dated all sorts of women before finally snagging himself the lovely Donna Peele.

Charlie Sheen and Donna Peele

They ended up getting married and after a whole five months, they were just as quickly divorced. This may not have come as a surprise to people since he was known for being a ladies’ man. Four months after the divorce, Charlie went on record saying: “You buy a bad car, it breaks down.” Was he speaking about himself?

Robin Givens and Svetozar Marinkovic

Robin Givens is a name that comes up every so often in Hollywood. She was very well known in the 80s and she was probably most famous for being married to Mike Tyson, who was the undisputed heavyweight boxing champion of the world at that time. After a memorable interview, she and Tyson had with Barbara Walters on 20/20, their marriage went sour and they were soon divorced. Robin Givens was called the worst woman on the planet because a lot of people thought she was trying to drain Tyson of his money along with help from her mother.

Robin Givens and Svetozar Marinkovic

Robin has largely been forgiven since then and she got married to her tennis instructor Svetozar Marinkovic. This marriage was short also, as it only lasted for one day! She may have broken the shortest marriage record in Hollywood. Wow!

Jennifer Lopez and Cris Judd

Jennifer Lopez has been in several very high-profile relationships that have been plastered all over media outlets around the world and her personal life is still very much fodder for the tabloids. Years before she called it quits with Marc Anthony, she was going out with professional dancer/choreographer Cris Judd. They met when he was hired to perform in her video Love Don’t Cost a Thing. He danced his way into her life and they got married.

Jennifer Lopez and Cris Judd

The dance was over after seven months with the marriage lasting just 218 days before they split. That divorce probably cost Ms. Lopez a sizeable fortune to so quickly dissolve.

Mario Lopez and Ali Landry

There is a good reason why this marriage ended. Mario Lopez and Ali Landry seemed to be the perfect couple. They dated for six years before they decided to take their relationship to the next level. Mario and Ali were said to be truly in love with each other and everyone around them commented on how perfect they are as a couple. They eventually got married and had a happy marriage for a very short time.

Mario Lopez and Ali Landry

Why was marriage ended so soon? Mario Lopez cheated on Ali Landry. They were married for only two weeks and then the divorce swiftly followed. Ali discovered that Mario was cheating on her and Mario was interviewed by Howard Stern when he explained that he was “bouncing around” Mexico with his cousins. “I had no business of being in that position,” before he went on to say that he “messed around” with another lady.

Eddie Murphy and Tracey Edmonds

Eddie Murphy and Tracey Edmonds started off as friends before they decided to get married. The power couple weren’t together long but got married in style. They went to a private island off Bora Bora and spent a ton of cash on a wedding of Hollywood caliber. Being such close friends should have worked in this marriage and Hollywood insiders thought their union would last for a long time.

Eddie Murphy and Tracey Edmonds

Their marriage lasted a good two weeks before Eddie and Tracey called it quits. During the honeymoon, Eddie started yelling at Tracey in front of some innocent bystanders who were minding their own business. So much for their friendship.

Carmen Electra and Dennis Rodman

The electrifying Carmen Electra happened to get married to one of the most eccentric athletes in the history of basketball. Dennis Rodman was known for his outlandish behavior, whether it occurred on or off the court. He and Carmen Electra randomly hooked up and soon after they got married.

Carmen Electra and Dennis Rodman

This wedding was short-lived. There may have been a purpose behind the wedding, such as a publicity stunt or something of that nature. Carmen may not have been able to handle Dennis Rodman’s strange behavior. Whatever happened, their marriage lasted only nine days. The wedding allegedly occurred as a result of a drunken get-together in Las Vegas, according to Dennis Rodman.

Dennis Hopper and Michelle Phillips

The marriage that occurred between actor Dennis Hopper and singer Michelle Phillips was not a long one. Perhaps this was just another case of two like-minded actors trying to find love in the hustle and bustle of Hollywood. Dennis and Michelle got married on Halloween in 1970.

Dennis Hopper and Michelle Phillips

The power couple was only married for only eight days before the wheels completely fell off their marriage. Dennis Hopper was known for having severe relationship problems, and the marriage was more than likely doomed from the start. The couple went their separate ways and they didn’t really open up about what happened after their quick union completely went off the rails.

Britney Spears and Jason Alexander

Britney Spears and Jason Alexander were childhood friends who became lovers. The couple would admit that they always shared a strong bond, although it hadn’t progressed romantically at first. Britney Spears and Jason Alexander were probably so good at being friends that when it came time to be lovers, it was just too weird.

Britney Spears and Jason Alexander

The marriage between Britney and Jason took place in Las Vegas and 55 hours later, they ended up getting a divorce. The reason behind the divorce was [according to the petition to annul the marriage] “Plaintiff Spears lacked understanding of her actions to the extent that she was incapable of agreeing to the marriage.” Like Dennis Rodman, she might have been way too drunk and was not in her right mind when she decided to tie the knot.

Tara Reid and Zack Kehayov

This is a rather weird story about the marriage of Tara Reid and Zack Kehayov. Tara Reid announced over Twitter that she was engaged to Zack Keyahov and announced her marriage to him all in under 24 hours. This may have been the fastest Hollywood engagement of all time. The marriage occurred in August of 2011.

Tara Reid and Zack Kehayov

Two months later the marriage between Tara Reid and Zack Kehayov came to an end. Many folks could see the end right before the marriage even began. There was not enough time to build a connection before their wedding and Tara went on record to say that the marriage was not legal in America in February of 2012.

Elizabeth Taylor and Conrad “Nicky” Hilton

Back in the day, short celebrity marriages still managed to last longer than they do today. This was the case for Elizabeth Taylor and Conrad “Nicky” Hilton, whose relationship lasted a whole eight months! It probably didn’t help that Elizabeth married him at the young age of 18. Even back then young kids were making bad decisions in the name of love — some things never change!

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Although they really did try to make things work, Conrad’s love for drinking and gambling eventually led to the demise of their relationship. After their separation, she took back her maiden name and gave marriage a whirl again, which worked out pretty well the second time around.

Janet Jackson and James DeBarge

Janet Jackson did something not too surprising, yet shocked her fans and family when she eloped with DeBarge, a member of another inclusive R&B act. Although it is not too unusual for a Jackson to make shocking decisions, this one wasn’t permanent.

Janet Jackson and James DeBarge

After only four months, their couple’s time of playing house was over and done, and the relationship was essentially finished as quickly as it seemed to have started. However, in 2016, there were rumors started by DeBarge that he and Jackson ended up having a secret child together. Juicy stuff.

Chris Kattan and Sunshine Tutt

SNL star Chris Kattan finally married his model girlfriend Sunshine Tutt after three years of date. One would think this marriage would actually stand a chance since they actually dated for a little while instead of tying the knot just because they felt like it in the spur of the moment.

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Even after three years of romance and an over-the-top lavish wedding, the entire union fell apart and ended in divorce only two months later. She walked away with a six-figure settlement, and he got a massive hole in his bank account. Hmm, sounds a little bit fishy.

Zsa Zsa Gabor and Felipe de Alba

This failed relationship has got to take the cake. Although Zsa Zsa Gabor has had many failed marriages in the past, her marriage to Felipe de Alba sets the bar for all failed marriages. The couple only managed one day of wedded bliss before they separated. This makes some failed marriages on our list look almost successful.

Zsa Zsa Gabor and Felipe de Alba

In 1986, she married her latest husband Frederic von Anhalt after eight other failed marriages. I don’t know about you, but that sounds like a divorce waiting to happen if someone has had eight failed marriages with one of them only lasting a day!

Michael Jackson and Lisa Marie Presley

Of all of these marriages, this one by far has the most interesting “how we met” story. The two first met when Presley was seven years old. After attending several of Michael Jackson’s concerts in Las Vegas, her father, Elvis Presley, introduced the two in 1974.

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However, their adult relationship did not begin until 1992, so we don’t have to worry about anything too weird with Jackson this time. In true Michael Jackson fashion, he proposed over the phone and Presley said yes. Surprisingly, the marriage lasted a full two years and they continued to date for more than four years after their divorce.

Helen Hunt and Hank Azaria

After dating for a little over six years, it seemed like this couple was ready to take the next step in their relationship and seal the deal for good. Although their relationship seemed to be a bit random, it looked like it was working out for the both of them.

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In 1999, the two got married but unfortunately, married life got the best of them and they divorced a mere 17 months later. However, if you still want to see them together, you can watch old episodes of Mad About You to see the two in action. Looks like they worked better professionally then emotionally.

Jennifer Garner and Scott Foley

Although it’s almost impossible to see Jennifer Garner with anyone except the bad boy Ben Affleck, at one point in time, she had a little something going on with clean-cut actor Scott Foley. The two were married in 2,000 and it looked like a promising relationship at the time.

Jennifer Garner and Scott Foley

However, their marriage only lasted a little over three years. But still, that’s not the worst amount of time we’ve seen yet, not even close. It’s okay, it all worked out for Jennifer in the end!

Ryan Reynolds and Scarlett Johansson

This is one particular relationship that was actually quite shocking to the public when it all fell apart. Both Ryan Reynolds and Scarlett Johansson match each other perfectly in both charisma, looks, popularity, and skill.

Ryan Reynolds and Scarlett Johansson

So, when they got hitched in 2008, everyone assumed this would be one of the few Hollywood couples who could withstand the test of time. However, in 2011, the world was shown otherwise. Although it was tragic, it apparently just wasn’t meant to be, since each one found their next spouse not long after their break up.

Drake and Rhianna

Although technically their story first began in 2005 after Drake fell in love when they first met, nothing really happened until 2009 when they allegedly first kissed. In August 2016, the two decided to make themselves public and even started kissing onstage, along with some other more intimate actions.

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However, all good things must come to an end, and it has been reported that the two are no longer exclusive. Poor Drake. As if he wasn’t already destroyed by enough girls, he can now add Rihanna to that list.

Scarlett Johansson and Sean Penn

I’m not entirely sure how Sean Penn managed to pull this one off, but I tip my hat to him. It is noted that the two got together relatively quickly in early 2011 after Johansson’s falling out with Ryan Reynolds in 2010.

Scarlett Johansson and Sean Penn

The two vacationed together in Mexico in early March, attended Reese Witherspoon’s wedding as a couple, and shred an intense makeout session at the White House Correspondents’ dinner in April. However, the couple called in quits in May of that same year. Short and sweet, but it looks like they both had fun.

Cher and Greg Allman

Back in July 1975, Cher and rock star Greg Allman hightailed it to Las Vegas and got hitched. This was also only a few days after Cher’s divorce was finalized with Sonny Bono, so no time was wasted!

Cher and Greg Allman

After their spontaneous marriage, Cher filed for another divorce just nine days after she and Allman made their fateful decision, after realizing that his booze and drug tendencies were too much for her. She hasn’t always had the best pick in men but she definitely learned a lot faster this time around!

Ethel Merman and Ernest Borgnine

Even back in the 1960’s celebrities were making bad decisions to get married without putting any real thought into their future. And just like today many of those marriages fell apart almost as quickly as they first started.

Ethel Merman and Ernest Borgnine

This is exactly what happened to Ethel Erman and Ernest Borgnine who were married in 1964. The couple put a lot of modern-day actors and actresses to shame when they filed for divorce only 32 days later. This was not the first rodeo for either one of the highly acclaimed Hollywood stars. Ethel had been married and divorced four times, and Borgnine five..

Taylor Swift and Tom Hiddleston

This pair was an odd couple, to begin with, so it was no real shocker that their fling only lasted for around 3 months. It is said that Taylor was the one that broke things off due to the drama surrounding the entire relationship. Maybe she needed inspiration for her next hit album?

Taylor Swift and Tom Hiddleston

It was stated that there was too much pressure, including from Taylor’s fans who didn’t take to the whole thing. It was a good look for Tom to be dating Taylor, but not the other way around because it was the Taylor show and Tom was just an extra in it. Tough break, man.

Nicky Hilton and Todd Andrew Meister

Before getting into an expensive love-triangle lawsuit with his assistant, Todd Andrew Meister was on the front pages of magazines for marrying Nicky Hilton in a quick Las Vegas wedding in 2004. In August, around 2:30 am, it became official with Paris Hilton being Nicky’s bridesmaid and Jeff Beacher the best man.

Nicky Hilton and Todd Andrew Meister

The wedding was said to be beautiful with high energy (how could it not be at 2:30 in Vegas?) Just as soon as it happened, it ended, and the two were divorced no less than three months after their Vegas extravaganza.

George Clooney and Talia Balsam

George Clooney was once established as the unattainable bachelor until he married his current wife in 2014. Because of this, it is usually forgotten that for a brief period of time he was married to Talia Balsam from 1989 until 1993.

George Clooney and Talia Balsam

The two got married in Las Vegas on December 15, 1989, yet their marriage only lasted for a brief four years. Clooney recalls the entire situation by saying, “I probably-definitely- wasn’t someone who should have been married at that point. I just don’t feel like I gave Talia a fair shot”. However, despite their split, they still remain friends.

Macaulay Culkin and Rachel Miner

Macaulay Culkin and Rachel miner got engaged in 1998 and exchanged vows a year later. They were both 17 at the time, so we can see where this is going. What they didn’t realize when they decided to get married was that it would transform their love affair into a not-so-solid husband and wife relationship.

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Their marriage didn’t last long with them ending their relationship in a divorce in 2000. It was later revealed, not so surprisingly, that everyone was against their relationship, especially their parents, which made it incredibly difficult to maintain their closeness. Much like Clooney and Balsam, the two didn’t take their split hard and are still friends today.

Drew Barrymore and Jeremy Thomas

Drew Barrymore was just 19 when she decided it was a good idea to marry a welsh bar owner after just six weeks of dating in 1994. However, it only took her about two months of marriage to discover that she desperately needed a divorce.

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We could let this one go, saying it was a bad decision of a youthful girl with too much popularity and money, however, this is the second time she’s been on this list. Maybe Drew should take a step back before she keeps throwing herself into random marriages.

Russell Brand and Katy Perry

After some time dating, the couple decided to tie the knot in India in 2010. However, the marriage quickly fell apart when Brand let Perry know through a text message that he was filing for a divorce. In an interview, Brand noted that their marriage only lasted for two years because of the “undulating nature of fame.”

Russell Brand and Katy Perry

He explained that it was both of their busy schedules that was the real issue as to why their marriage didn’t work. He still has warm feelings towards her, but it is unlikely she feels the same.

Johnny Depp and Amber Heard

In February 2015, Johnny Depp and Amber Heard shared a lavish island wedding ceremony together. Although the couple seemed happy for a while, the news came out of nowhere when Amber filed a restraining order on the 53-year-old actor. She claims that there was domestic abuse occurring in their relationship.

Johnny Depp and Amber Heard

After a lot of ambiguity and back-and-forth, the two finalized their divorce in January 2017. Although there still hasn’t been enough proof to establish if these claims are true, it’s another short-lived celebrity relationship to add to our list.

Amy Winehouse and Blake Fiedler Civil

Amy and Blake’s relationship was a very public affair when it was going on. Both of them wrote songs about each other, and their relationship was under the constant microscope of the public eye.

Amy Winehouse and Blake Fiedler Civil

The two were married in Florida in 2007 but Blake filed for a divorce in January 2009, after photos of Winehouse with another man in the Carribean emerged. During the divorce, Amy admitted that she was on and off drugs during their time together and that her relationship with Blake was solely based on doing drugs together.

Jennifer Aniston And Adam Duritz

Jennifer Aniston is an icon, but in 1995, Friends was only one season in and Aniston wasn’t yet at the top of her game. The actress dated the lead singer of the Counting Crows, Adam Duritz. Their relationship was so short, many haven’t even heard of it. It sounds to be more like a fan-fling, as Duritz claims “We never even slept together.”

Jennifer Aniston And Adam Duritz

Even if it was just a fling, Aniston was probably a little bothered when Duritz quickly moved on to her Friends co-star and good friend, Courtney Cox! Although it’s better than getting sloppy seconds.

Kirsten Dunst and Justin Long

This relationship wasn’t welcomed with open arms by fans, as Justin Long had just left a serious relationship with actress Drew Barrymore when he was spotted soon after with Kirsten Dunst in 2014. In fact, it wasn’t the first time that the two actresses have dated the same man, as they also both dated Fabrizio Moretti, the drummer of The Strokes.

Kirsten Dunst and Justin Long

Barrymore and Dunst seem to have the same type in men, or maybe men are drawn to similarities they share. It was only two months when Dunst called it quits with Long. Dunst is now engaged to her Fargo co-star Jesse Plemons.

Kristen Cavallari And Nick Lachey

This reality TV star and boy band heartthrob duo didn’t last long. They briefly dated in 2006, when Kristen Cavallari was fresh out of Laguna Beach High School and Nick Lachey had just divorced artist Jessica Simpson.

Kristen Cavallari And Nick Lachey

Their relationship was barely a blip on the radar, Lachey began dating his now-wife Vanessa Minnillo that same year after she appeared in his music video. That’s no loss for Cavallari, who is now married to NFL quarterback Jay Cutler. Both Lachey and Cavallari have three children and are amicable when they are at the same events.

Alyssa Milano And David Arquette

Just as actress Alyssa Milano’s career was in full swing as she played Samantha Micelli on Who’s The Boss, she briefly dated actor David Arquette. This was back in 1991 when Milano had just split from Corey Haim, and Arquette had not yet met his now-wife Courteney Cox.

Alyssa Milano And David Arquette

In the few photos of the two together, they’re smiling and look very cute together. But for how short their relationship was, it was probably more of a friendly fling. Milano is now married to an agent by the name of David Bugliari.

Carmen Electra And Simon Cowell

So this one is pretty unexpected. While they’re both known for their fiery personalities, you wouldn’t piece together that Carmen Electra and Simon Cowell would be seen cuddling up together- but it happened. This was in 2012, and Electra had split from ex-fiance Rob Patterson and began appearing on a dating TV show called The Choice, where she was featured as a celebrity bachelorette.

Carmen Electra And Simon Cowell

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The couple only lasted from December 2012 to February 2013. While most people dodge relationships during the holiday season, perhaps this unlikely duo was caught up in the magic, that quickly vanished just a couple months later.

Mischa Barton And Luke Pritchard

Actresses and musicians seem to play well together, as actress Mischa Barton and The Kooks frontman Luke Pritchard are another duo on this list. Like the rest, their relationship was a short one, lasting from December 2008 to March 2009. They started out as friends and ended as friends.

Mischa Barton And Luke Pritchard

After the breakup, Barton wrote on her blog. “I think Luke is a great guy, but the type better suited as a friend. We have a surprising amount of mutual friends in England and I don’t regret our time together, I just couldn’t keep it going.” Ouch, sounds like one of those tales of nice guys finishing last.

Nicole Kidman and Lenny Kravitz

What?! Yep, Nicole Kidman has a thing for musicians too. After she divorced Tom Cruise, but before she married Keith Urban, Kidman was engaged to Lenny Kravitz. Yes, engaged. Kidman and Kravitz met and began dating in 2003 and quickly became secretly engaged.

Nicole Kidman and Lenny Kravitz

They must have had a feeling that it wouldn’t work out because they kept it a secret until they broke up, less than a year later. “It just wasn’t right. I wasn’t ready. We weren’t ready,” she later told Vanity Fair.

Giselle Bundchen And Josh Hartnett

Well, Josh Harnett certainly looks happy here, and who wouldn’t be, with their arm around supermodel Giselle Bundchen? The actor and supermodel had a fling in 2000, just before Bundchen began dating Leonardo DiCaprio- this woman has quite the list of lovers!

Giselle Bundchen And Josh Hartnett

Harnett, on the other hand, stayed out of the public eye with his relationships and turned to activism. He confirmed he was in a relationship with English actress Tamsin Egerton, and the two quietly had two children together. It’s no secret that Bundchen went on to marry New England Patriots quarterback Tom Brady in 2006.

Renee Zellweger And George Clooney

George Clooney is one of the dreamiest guys in Hollywood, so it’s no surprise that the actor ended up on this list twice. This time, it’s for his relationship with actress Renee Zellweger. While Clooney is now happily married to Amal, he dated around quite a bit in the 1990’s and 2000’s.

Renee Zellweger And George Clooney

It was 2001 that he dated Zellweger for a short time.

In 2008 they both starred in the film Leatherheads, where they play each other’s love interests. That sounds like it could be extremely awkward, however, Zellweger said of their chemistry, “Oh, there’s a natural comfort there, absolutely.”

Tara Reid And Carson Daly

Yep, another person to appear twice on the list is Tara Reid, for her relationship with host Carson Daly. Reid has a long history of rushed romances, and this one was no different. The pair met on Total Request Live in March of 2000 and began dating right away.

Tara Reid And Carson Daly

Before The rest of us could catch up, they moved in together in an apartment in New York City. By the end of October, they were engaged. Maybe their friends and family stepped in to help them hit the brakes on their hot and heavy romance because by June of the following year, they announced their split.

Cameron Diaz And Sean Combs

We bet you didn’t think of that one. But it’s true, actress Cameron Diaz and Artist and Producer Sean ‘Diddy’ Combs were romantically involved in 2008. While both their reps repeatedly denied their relationship, It was clear that something was going on between the actress and entrepreneur.

Cameron Diaz And Sean Combs

Apparently, Diddy didn’t do all he could to woo Diaz, and he lost his chance with her. According to his friends, she’s the one that got away. “If I could turn back time, things would be different!”’ The Daily Mail reports Diddy saying over dinner in 2014. “She’s the sexiest girl in the world.”

Esther Nazarov And Fred Durst

Fred Durst, Limp Bizkit’s frontman, was a big name in the ’90s with hit singles and packed shows. It’s no secret that Durst loved the spotlight and was often the center of controversy. He once claimed he was in a relationship with Britney Spears, which her reps strongly denied.

Esther Nazarov And Fred Durst

In 2009, Durst quickly became engaged and married Esther Nazarov in where else, but Las Vegas. It may have been a drunken regret, as their relationship ended after only three months! He announced the split on Twitter, which happens to be the same way Durst announced their marriage.

Madonna And Dennis Rodman

In 1994, before her marriage to Guy Ritchie, Madonna dated NBA star Dennis Rodman, but for only a few months. Even though the romance didn’t last long, the couple way over-shared their experiences together, as many would expect when two sex symbols get together.

Madonna And Dennis Rodman

It sounds like there are no bad feelings between the two, after their brief romance. In 2015, during an interview with Us Weekly, Madonna described both Rodman and her ex Vanilla Ice, saying, “If I were trapped on a desert island with either Vanilla Ice or Dennis Rodman, I would pick Dennis,” she said. “He has a better sense of humor. Plus, he could always wear my clothes.”

Gemma Ward And Heath Ledger

Before his untimely death, supermodel Gemma Ward dated actor Heath Ledger in 2007. They’re both Australians, born in Perth, and shared a connection. Their relationship didn’t last, maybe because Ledger had recently split from his long-term relationship with Michelle Williams, but Ward remembers him lovingly after his tragic death in 2008 at the age of 28.

Gemma Ward And Heath Ledger

In 2011, Ward told the Herald Sun, “There was no one like him – and no one will ever be like him,” she said. “I’m just so grateful I got to meet him and get as close as I did with him.

Kate Hudson And Lance Armstrong

Kate Hudson doesn’t keep her love life a secret, as she’s dated Alex Rodriguez, Dax Shepard, Owen Wilson and others. She’s also been caught making out with quite a few stars, but we’re here to talk about her relationship with the golden boy gone bad, Lance Armstrong.

Kate Hudson And Lance Armstrong

Hudson and Armstrong dated for a couple of months in 2008 and were in You, Me, and Dupree together. That might raise a few eyebrows, as she was dating Owen Wilson on-again-off-again during that time as well. Hudson was spotted spending time with Armstrong and his kids in Austin, but their relationship has long since fizzled out.

Rachel McAdams And Josh Lucas

Rachel McAdams perhaps fulfilled many peoples’ dreams when she began dating her Notebook co-star and love interest Ryan Gosling. However, that romance ended and she turned to actor Josh Lucas in 2009- for a minute. They were spotted cuddling and kissing on the streets of Canada in early March, where McAdams lives.

Rachel McAdams And Josh Lucas

However, the chemistry wasn’t there as much as it appeared, and the couple quickly split. In 2011, Lucas went on to get engaged after six weeks of dating writer Jessica Henriquez, but unfortunately, they divorced in 2014. Taking the time to get to know someone is not overrated!

Kat Von D And Jesse James

Kat Von D is the tattooer who rose to fame in Miami Ink and started her own show, LA Ink. She’s previously dated Nikki Six, Steve-O and others, and started dating Jesse James in August of 2010, just months after Sandra Bullock filed for divorce with James. Also that year, more women came out and said they slept with James during their marriage.

Kat Von D And Jesse James

That didn’t bother Von D- at first. Less than a year after they started dating, the pair became engaged in January of 2011. But, once a cheater, always a cheater, and James went back to his old ways. They called off the engagement in July 2011.

Avril Lavigne And Chad Kroeger

Okay, this was an unlikely duo from the start. While both hailing from Canada, and both musical artists, their sounds are quite different from one another. Anyway, after divorcing Sum 41’s Deryck Whibley, Lavigne dated Brody Jenner before meeting Chad Kroeger in July 2012. After dating for only one month, Kroeger, who had never been married before and was nine years older than Lavigne, proposed. The pop rocker said ‘yes’ and they were engaged in August 2012.

Avril Lavigne And Chad Kroeger

By September 2015, Lavigne announced on Instagram that the couple had separated. In March of the following year, however, the couple was spotted together, igniting rumors that they may be trying to rekindle their romance.

Kaley Cuoco And Ryan Sweeting

After three months of dating, actress Kaley Cuoco and professional tennis player Ryan Sweeting became engaged in September 2013 and were married by the end of the year. Talk about a whirlwind romance! Of their marriage she described herself as a happy housewife, “I cook for Ryan five nights a week: it makes me feel like a housewife. I love that. I know it sounds old-fashioned, but I like the idea of women taking care of their men.”

Kaley Cuoco And Ryan Sweeting

Sadly by September 2015, the couple announced that they were getting a divorce. Cuoco is now dating equestrian Karl Cook.

Scarlett Johansson And Jared Leto

Jared Leto has dated and been spotted with many, many starlets of Hollywood, including Cameron Diaz, Ashley Olsen, Lindsay Lohan and Paris Hilton. Scarlett Johansson gave him a shot in 2004, and by the sound of it, she wishes she didn’t. The relationship lasted less than a year, but Johansson describes how she hit ‘rock bottom’ while dating him.

Scarlett Johansson And Jared Leto

She told Cosmopolitan, “Long, long ago, I had someone in my life who was forever unavailable… but, like, so attractively unavailable. Rock bottom is the moment when you’re like, ‘I’ve lost myself. This isn’t me.'” Plus, anyone who checks their phone while kissing Johansson doesn’t deserve her in the first place!