Did you know that Richard Gere had it going with Cindy Crawford during the Julia Roberts and “Pretty Woman” days? Were you aware that the princess of rock n’ roll married the King of Pop? The celebs dated one another in turns, making sure they all got a taste of each other. Now, you tell us how many times Johnny Depp appears on the list.
Alyssa Milano and Corey Haim
Like many child stars (and adult ones), Corey Haim had substance dependency issues during the 1980s'. He was a teen idol and dated some young ladies during those days, with Alyssa Milano being the most famous of them all.
She was a huge star at the time, with "Who's the Boss?" and would go on to be an even bigger star with roles in hit shows like "Charmed" and "Mistresses". They dated for a few years and broke up at the beginning of the 1990s'. He must have left his mark on Alyssa's life, as she was devastated when she learned about Corey's passing in 2010.
Dennis Quaid and Lea Thompson
The movie "Jaws- 3" brought us a bit more than scary sharks. In 1996, Lea Thompson and Dennis Quaid (who starred in the movie) were seriously dating, and Dennis even proposed. The two were engaged for almost a year but never took the next step.
A few years later, Thompson started to date Howard Deutch, who she met on the set of "Some Kind of Wonderful" and ended up marrying. It seems that Lea Thompson has a thing for men she meets on sets. Then again, these things are bound to happen when people are literally paid to play each other's love interest.
Gwyneth Paltrow and Brad Pitt
In the 1980s and 1990s, you couldn't get better looking than Brad Pitt and Gwyneth Paltrow. They were the most glamorous couple of that era and were adored by all. They dated for two years, which at the time seemed like a lifetime.
A few years later, Gwyneth Paltrow admitted that their relationship ended because she was in a very unstable time in her life and that she practically messed it up. You never know; Paltrow could have saved us the whole Anniston-Jolie story if she would have stuck around. Though it seems like they both landed on their feet eventually.
January Jones and Ashton Kutcher
January Jones and Ashton Kutcher were pretty much leveled out when they first met in 1998. They were both in the spring of their careers, still taking any role proposed, and were working their way up the success ladder. They dated for three years and decided to go on their separate ways in 2001.
Jones has remarked on several occasions that Kutcher was not the ideal partner and was not supportive of her career at all. Since then, the couple kept climbing, though separately. Jones went on to star as Betty Draper in "Mad Men" and Ashton went on to marry Mila Kunis.
Drew Barrymore and Luke Wilson
Many couples start their love story on the sets of a movie, and so did Luke Wilson and Drew Barrymore. "Home Fries" and "Best Man" were where it all began for these two. It must make things so easy when your on-screen partner is your real-life partner. They started to date in 1997 but only lasted until 1999.
Barrymore has said in a number of interviews that Luke Wilson is one of the most important people in her life and that she has been privileged to have known him. We feel he's not the only guy Drew said this about...
Madonna and Sean Penn
Sean Penn and Madonna met in the winter of 1985 and married soon after, in August of the same year. That's a good way to make one year the best in less than six months. "True Blue", one of Madonna's greatest albums, was, in fact, dedicated to Penn.
In January 1989, just before celebrating their fourth anniversary, they decided to call it quits and got divorced. None of them seems to have wallowed in it for too long. They have since moved on, with Sean Penn remarrying twice (one to actress Robin Write and once to actress Leila George) and Madonna remarrying once (to filmmaker Guy Ritchie).
Melanie Griffith and Don Johnson
Don Johnson and Melanie Griffith starred in the last three decades of the 20th century. The mid-1970s is when it all began. Less than a year after they married, they already got divorced, only to retie the knot in 1989.
That second round only lasted for five years during which the two became parents to actress Dakota Johnson who you probably know from the 50 Shades franchise. The mid-1990s were the days when Jonson and Melanie eventually realized that they weren't meant to be, and 1996 was the year they ended the love story for good. What a rollercoaster of a relationship!
George Clooney and Kelly Preston
We bet you never knew that Mr. Nespresso, George Clooney, had a guest appearance on the 1980s show "The Facts of Life." Well, he did, and at the same time (and we didn't know this until researching for this article), he dated Kelly Preston before she went off and married John Travolta.
They dated in 1988, which lasted for only a year, but during that year, they moved in together and even raised a pet pig named Max! After the breakup, Clooney kept the pig and raised it until died at the old age of 18. Who knew he had it in him?
Julia Roberts and Matthew Perry
A pretty woman and one of the funniest guys in the house kicked it off, apparently in 1995. Julia Roberts, known for her remarkable performance in many widescreen movies, was a guest star on "Friends," Mattew Perry's home set. Ironically, Roberts played the role of someone who gets payback on Perry's Chandler for bullying her in school.
The two enjoyed each other's company for almost a year before deciding to end the romance. It is thought that this was the turning point for Mattew Perry, as his drinking problem is said to have begun slightly after the breakup, but this is all hearsay.
Sandra Bullock and Matthew McConaughey
These two did a very good job of hiding their relationship. So much so, that by the time the tabloids realized they were an item, they had already broken up. Apparently, Bullock and McConaughey were together for almost two years and even got engaged secretly! They met in 1996 and immediately felt the sparks while filming on the same set.
For their own reasoning (they kept this a secret, too), they decided to go on their separate ways; however, they have remained close until today. They are very close friends and make it a point to share it with the world.
Arsenio Hall and Paula Abdul
"American Idol" judge Paula Abdul dated Arsenio Hall, who had his very own show. The two met on the set of a movie and lived hectic lives in the entertainment industry. They met while filming "Coming to America," which was a classic Eddie Murphy comedy, and became inseparable.
Even though they broke up, Arsenio mentions that he has only good memories of Paula. They stayed friends, and she even appeared on his show after they broke up. Abdul has since married twice (actor Emilio Estevez and fashion designer Brad Beckerman) but Hall has never married, though he does have one son.
Janice Dickinson and Rob Lowe
Like everyone in the 1980s', all men wanted to be Rob Lowe, and all women wanted to date Rob Lowe. And Janice Dickinson is one woman who actually did that. 1988 was the year it all happened, though it only lasted a few months.
She was a stunning supermodel who escalated her career and later became one of the judges on "America's Next Top Models," in addition to being a successful businesswoman and author. Rob Lowe, on the other hand, is a loved actor, producer, and director, but the 1980s will always be remembered as his peak and pride decade.
Cher and Val Kilmer
Movie stars and musicians of the 1980s and 1990s', practically lived in the same bubble. They mixed with the same people, mingled at the same parties, and dated the same loved ones. Cher, who was at the peak of her career in those days, set her eyes on Val Kilmer, who later co-starred in "Top Gun" with Tom Cruise.
They were a hot item between 1982 and 1984 and then called it quits. Cher said that Kilmer was much younger than her, which was a big issue back in the day, and that older guys (or guys the same age as she was) just weren't interesting enough for her.
Michal Jackson and Brooke Shields
Unlike today, at the beginning of the 1980s, things were different, and the number of stars was limited. Not every artist that came up with a new song instantly became famous, whereas today, you don't need much to be recognized worldwide. Michal Jackson, at the time, was known and loved globally. As was Brooke Shields
He dated Brooke Shields for a while, but apparently, they weren't both aligned with how they wanted things to go. Jackson proposed a number of times; however, Shields tells a different story and has always claimed that they were no more than two good friends.
Christina Applegate and Brad Pitt
In the 80s, Brad Pitt and Christina Applegate were (like many well-known stars at the time) in the spring of their careers. Pitt just started to walk through the path of fame, and Applegate was breaking through with her role in "Married With Children."
These two were friends as teenagers. Pitt (together with other future stars such as Jason Priestly) would come to her parent's house for Sunday lunches. Pitt was even her date to the 1989 MTV Movie Awards, though she left with someone else… awkward! They both went on to other partners eventually, though. Applegate is now married to musician Martyn LeNoble, and Pitt, well... we all know what happened with him.
Christine Taylor and Neil Patrick Harris
Dr. Doogie Howser is not all a goody two shoes. Way before he came out and revealed to the world his orientation, he dated actress Christine Taylor. She is best known and loved for her role in "The Brady Bunch" and in "The Wedding Singer." They dated from 1997 until 1998. A relationship that lasted just over a year.
They were a relatively private and quiet couple, with not too many horror stories to make the paparazzi's day. These days, Doogie is happily married to David Burtka, and Christine is married to Ben Stiller, also in a very happy way.
Robert Downey Jr. and Sarah Jessica Parker
Way back in the 1980s, Robert Downay Jr. was still unknown for his roles as "Iron man" in the MCU. In fact, he was so out of it with his substance dependency that it seems that Sara Jessica Parker came just in time to put him back on his feet.
The two were filming a movie together, ending in a seven-year relationship. Downey found it hard to let go of his former lifestyle, which was difficult for Parker to handle. Since then, he has left his mark in "Chaplin" and "Sherlock Holmes," and Parker has left us wondering whatever happened to Mr. Big and the City.
Lisa Marie Presley and Michael Jackson
This is about as good as it gets. The King of Pop dated the King of Rock n Roll's daughter. AKA the Rock n Roll princess. The early 1990s were the days when everything was about Michael Jackson's legal accusations, and Lisa Marie managed to make the wind blow in a different way.
Lisa Marie even famously starred in Jackson's music video for his ballad "You Are Not Alone". They were married for under two years and had no children together, yet they managed to preserve their titles, which they both left as their legacy following each of their deaths.
Winona Ryder and Matt Damon
Sometimes in life, all you need is a best friend to introduce you to their partner's best friend, and there you go. You get yourself a boyfriend. In the late 1990s', Gwyneth Paltrow was Winona Ryder's best friend. Paltrow was also dating Ben Affleck. Matt Damon was Affleck's best friend and you can see where this is going.
The two hit it off and a match was made. Damon and Ryder dated for over three years and were known as Hollywood's hottest couple back then. Matt Damon quickly moved on to his next story in life, and Winona Ryder wasn't left far behind.
Elle Macpherson and Billy Joel
Apparently, you don't have to be the best-looking guy in the class to date the most beautiful girl around. Well, that's how it was back in the 1980s'. Back then, the known and loved "Piano Man" was (and still is) a successful musician and one of the best-selling artists of all time.
During those days, Joel started to date Elle Macpherson, who back then was (and still is) a beautiful model making her way through law school (though that law part was only true for about a year). The two dated for a short time and then decided to go their own way.
Courtney Love and Edward Norton
Courtney Love's most famous relationship was and will always be the one she had with the late Kurt Cobain but this entry is about a different relationship. The movie "The People vs. Larry Flynt" is where it all began. Norton and Love co-starred and started to date shortly after. They dated for over four years, which turned them into a well-known couple in the Hollywood scene.
Like all couples, they had their ups and downs. However, their downs seemed to make the headlines way too often. In 1999, Courtney Love practically ditched Edward in the middle of a fight and never returned.
Alyssa Milano and David Arquette
When you get into show business at a very young age you are bound to have at least one VIP relationship. Alyssa Milano was under the age of 20 when she began her romantic affair with David Arquette. Those were the shining days of "Who's The Boss?" for Milano and the days of "The Outsiders" and "Parenthood" for Arquette.
There was such a buzz covering these two back in the day that you might have thought there was a huge love affair going on between them. The truth is, their story lasted for just over 60 days, turning this romantic episode into a 60 minutes show.
Jon Bon Jovi and Diane Lane
Diane Lane is best known for her role in the 1979 movie, "A Little Romance." Only years later, she returned to the public eye with the 1989 TV series, "Lonesome Dove." Since then, she has captured our hearts in numerous roles and has left her mark in Hollywood.
During her 20s, she dated Jon Bon Jovi, who, in those days, did no more than sweep floors and write songs. It was only at the end of the 1 Nowadays, the man is happily married to the same woman (Dorothea Hurley) since 1989.980s that Bon Jovi became the Bon Jovi we know and love today.
Jennifer Grey and Matthew Broderick
Before Jennifer Grey put on her dirty dancing shoes, she starred in the 1986 huge teen hit "Ferris Bueller's Day Off," where Bueller was played by no other than Matthew Broderick. Funnily enough, in the movie, they played siblings who were always at each other's throats, but the sparks between the two were still there and undeniably so. However, they were kept secret for quite a while.
Their romance was revealed shortly before "Dirty Dancing" was released, and not long after, they decided to call it quits. The two have since had their fair share of much-publicized relationships: Broaderick with actress Sarah Jessica Parker and Grey with actor Clark Gregg.
Tatum O'Neal and John McEnroe
In the 1980s', John McEnroe was a professional superstar tennis player. He is known for throwing his temper on the tennis court, eventually leading to conflicts with the tennis association. Tatum O'Neal is a well-known actress who snagged an Academy Award when she was just ten years old.
When these two met back in 1986, he was at the peak of his career, and she was dealing with an illegal substance issue, which didn't stop them from getting married. They ended their marriage in 1994, which was followed by an ugly court case, accusations on both sides, and a 1980's story to be told.
Drew Barrymore and Edward Norton
Everyone says I love you, and everyone loves Drew Barrymore. How could you not? She has "adorable" written all over her face. Drew Barrymore and Edward Norton starred together in "Everyone Says I Love You" but only started to date a few years later. In 1999, Barrymore escorted Norton to the Acadamy Awards, and the stars were glowing for the two.
Their relationship didn't survive the welcoming of the new millennium, and before 2000 burst into the world, the two went their separate ways. Norton's way has led him to marry his current wife, Shauna Robertson, and Barrymore's way led her to two marriages and two divorces.
Kristen Johnson and Ryan Reynolds
Between 1999 and 2000, the sun shone for Kristen Johnson and Ryan Reynolds. Back then, Reynolds was making it big on "Two Guys and a Girl," and Johnson was doing the same while starring on "3rd Rock From the Sun". For a while, these two had it going.
People are always looking for spicy or interesting relationship stories but they won't be getting them from these two, who seem to have ended things on good terms. In recent interviews, both couldn't come up with any juicy stories about their past, but Kristen did say that Reynolds was a one-of-a-kind kind of guy, just not suited for her.
Sylvester Stallone and Brigitte Nielsen
During the 1980s, Sylvester Stallone and Brigitte Nielsen were one relationship that was always starring at the top of the headlines. Most of the gossip around them was based on rumors, but plenty of it was based on real-life issues the couple went through.
Nielsen, a Danish actress who appeared on the UK "Big Brother Show," and Stallone managed to preserve their marriage for less than two years, and in 1987 the two went their separate ways. Today they are both happily married — Stallone to Jennifer Flavin (third and current wife) and Nielsen to Mattia Dessì (fifth and current husband).
Winona Ryder and Johnny Depp
The indie couple of the early 90s, Johnny Depp and Winona Ryder were the black sheep of Hollywood. Both dark-haired beauties that took on some quirky films, their love seemed like a match made in heaven. The two met in 1989 at the premiere of Ryder's film "Great Balls of Fire!" — the classic biopic of the late Jerry Lee Lewis.
By the time they co-starred in "Edward Scissorhands" in 1990, the world was enamored by them. Constantly overwhelmed by the press, the public pressures weighed on their relationship. Eventually, they gave in and, by 1993, decided to end it.
Heather Locklear and Tommy Lee
If you're from the 1980s', you probably remember Heather Locklear from "Dynasty". If you're from the 1990s', you are obviously a "Melrose Place" lover. Either way, Locklear was on top of the list, making her an icon of those decades. Tommy Lee was the Mötley Crüe drummer, and in 1996 they both tied the knot.
After him being unfaithful to her, they divorced in 1993, which allowed her to marry Richie Sambora, and allowed him to marry Pamela Anderson (and later Britney Furlan). It looks like Locklear has a thing for musicians, and Tommy Lee, for sure, has a thing for blondes.
Cameron Diaz and Matt Dillon
"A Kiss Before Dying," "Singles," and "There's Something About Mary" are only some of the movies Matt Dillon is recognized for. He might have been happily (or not so happily) married in the movies he starred in, but in real life, the facts are slightly different.
1995 was the year for Matt Dillon and Cameron Diaz, who was at the highlight of her career at the time. The relationship lasted for three years, and the two decided to break up in 1998. Rumors say Cameron wanted to take the next step in life together with Dillon. He, however, was nowhere near.
Jerry Hall and Mick Jagger
Models and rockstars go hand in hand like burgers and fries. Just ask these two. In 1991, lead singer and one of the founder members of The Rolling Stones, Mick Jagger, and actress-model Jerry Hall married in exotic Bali, Indonesia.
However, eight years later, their fairy tale marriage ended after Hall discovered that Mick had been unfaithful to her, which ended up with the third party bearing a child. It seems that as one of the most influential figures in rock and roll, you have one too many temptations. Jagger has fathered eight children with five women. Jagger, stick to music!
Lenny Kravitz and Lisa Bonet
Last century (ugh, we know it's technically true but we still get the creeps when we see those words in that context), Lisa Bonet was making it big as Denise Huxtable on "The Cosby Show," while Lenny Kravitz was making it big as a musician.
To us, they always seemed like the perfect match; however, things were not all stable for the two. They married not long after they met and divorced not long after they married. They had a daughter together, which will keep them in some ways together for as long as they live, whether they like it or not.
Sheryl Crow and Owen Wilson
The country, jazz, pop, and rock star Sheryl Crow has dated a few big names; the famous Eric Clapton is one of them. She never really settled down with anyone and never bore children of her own. She has, though, adopted two boys who she brings up alone.
Back in the 199os', Crow had an on-and-off relationship with Owen Wilson that ended not much longer after it started. Wilson is known for his unsteady ways when it comes to relationships, so the ending of this little romance story didn't come as a surprise to us. He later went on to have three children with three other partners.
Tom Cruise and Rebecca De Mornay
1983 was the year for Rebecca De Mornay and Tom Cruise. They were both working on the set of "Risky Business" at the time, which turned into a real-life romance. Apparently, while they were shooting the movie, Rebecca was already involved with Harry Dean, but this didn't stop her from starting a new relationship with Cruise. By 1985, the story between the two was over.
Tom Cruise had an amazing career in front of him, with "Top Gun" being the biggest success of those days, and Rebecca De Mornay went on to star in numerous movies, such as "The Three Musketeers," and "The Hand That Rocks The Cradle."
Gwyneth Paltrow and Ben Affleck
This story has somewhat of a circular structure: Ben Affleck and Gwyneth Paltrow met on the set of one movie and then had to meet again, after they had already broken up, to promote another movie. That, in itself, already sounds like a movie.
They first fell in love in 1998's "Shakespeare in Love," and by the time their 2000 flick "Bounce" came out in the year 2000, they were already apart. Gwyneth was quoted saying that Ben isn't the type of boyfriend you marry, but the one you date to heal childhood trauma. We don't know if that's a compliment or not.
Melissa Gilbert and Rob Lowe
Mellisa Gilbert spent most of her childhood years on the little prairie, so no wonder she fell madly in love with mega babe Rob Lowe when she first met him. We doubt it if there were charmers like Lowe on the prairie. Gilbert and Lowe went out for over six years, with a few breakups along the way.
At one stage, they got engaged, but that never led to a wedding. Rob carried on with his life, spreading his charms on other women, and Melissa nourished her career, became a producer and politician, and is happily married to Timothy Busfield.
Emilio Estevez and Demi Moore
Before starring as Andrew Clark, the athlete in "The Breakfast Club," Emilio Estevez was introduced to the stunning Demi Moore (who was still before her "Indecent Proposal" and "Ghost" days). They dated for a while and got engaged but never tied the knot.
They were both madly in love with one another, but apparently, that was not enough for Estevez to not play the game with another woman simultaneously. When Demi's therapist advised her not to take it any further with Emilio, she knew they had to go separately. But other relationships were not too far ahead for either of them.
Tyra Banks and Seal
In the 1990s, Seal was one of the biggest stars around, with his greatest hit, "Kiss From a Rose," winning several awards at the time. Seal is better known for his relationship with Heidi Klum (which was highly publicized but famously ended in a divorce), but before then, another supermodel was on the scene.
Seal and Tyra Banks dated for three months. Their relationship was kept relatively low-key, and besides one event that they appeared together, no one made a fuss of them. In fact, other than Seal's marriage to Klum, both stars' love life didn't make too many headlines.
Corey Feldman and Drew Barrymore
The child stars of the 1980s were very different than the ones of today. Back then, if you appeared in one movie, you probably appeared in them all. During his teens, Corey Feldman starred in "Friday the 13th", "Gremlins," "The Goonies," and the all-time classic, "Stand by Me."
In 1989, Feldman dated Drew Barrymore, also known as a child star of those days. It's actually kind of sweet when you think about it — they were probably the only people who could fully understand each other. The two came together as an item to the Oscars that very same year.
Kate Moss and Johnny Depp
Johnny Depp and Kate Moss were quite an item for a hot minute. And by hit minute we mean about four years, between 1994 to 1998. In 2007, Johnny Depp was interviewed speaking fondly about Kate Moss, which would have made you think Moss and Depp had it going really well at the time.
Well, the truth is that it wasn't all that good. Their relationship came after Depp's love story with Winona Ryder, which became a huge story within the Hollywood tales and lasted for just over three years. All parties involved went on to have other high-profile relationships.
Cher and Tom Cruise
The iconic Cher can get away with almost anything. When she was a 38-year-old lady, she got away with dating a 22-year-old young man by the name of Tom Cruise. Now, we aren't really sure what they mean when they say "get away with" in this context. It's not like people (let alone people in Hollywood) get punished for a relationship with an age gap.
He was just taking his first footsteps in the Hollywood world, while she had already built her reputation as a successful singer. The two dated for a while, not turning their story into something great. They were busier smiling to the cameras than actually trying to make something work.
Gary Oldman and Uma Thurman
Uma Thurman is one you just gotta love. And Gary Oldman thought that, too, back in the 1990s. Oldman was Thurman's first true love, as she once said in an interview. She said she was a young and inexperienced woman involved with a man twelve years her senior.
She also said that it isn't a surprise that their relationship ended when it did — less than two years after they tied the knot. Uma even took it a step further by adding that this was the mistake of her life. He was 12 years older than her, and what was done has been done.
Madonna and Vanilla Ice
The queen of pop dating the king of ice cream. What a strange couple they were. There was a slight age gap between the two, and according to Vanilla's story, she taught him many things he didn't know about relationships.
They dated for just under a year and broke up because Vanilla Ice didn't approve of the book she released at the time, which exposed him in a disrespectful way. Now, we ask you, Mr. Vanilla, it is known that the queen says whatever is on her mind, anywhere, anytime, and about anyone. What exactly did you expect when you started to date her?
Tom Cruise and Nicole Kidman
You might have thought this golden oldie wouldn't get a mention on this list. But how could we forget the Nicole Kidman-Tom Cruise love story? Kidman met Cruise in 1989, during the filming of "Days of Thunder," and from her dating history, it seems she may have a thing for guys who are shorter than her.
On Christmas Eve of 1990, Kidman and Cruise got married. It was Cruise's second marriage at the time. They even adopted two children, Isabella Jane and Connor Anthony, while they were married. In 2001, the couple split. Cruise filed the divorce. In 2006, Kidman admitted that she still loved Cruise dearly, and it wasn't easy to totally erase him from her life.
Molly Ringwald and Anthony Michael Hall
Molly Ringwald and Anthony Michael Hall are the perfect examples of "when a beauty dates a geek." They both starred in the 1980's movies, "Sixteen Candles" and "The Breakfast Club," and dated for a short while after making these hits. These were 80s idols that were adored by teenagers all over the world who loved to see them together.
The fans grew up, and so did the stars, each going their separate way but remaining good friends until this day. Nowadays, Ringwald is married to American writer Panio Gianopoulos and shares a daughter with him. Hall is married to actress Lucia Oskerova.
Richard Gere and Cindy Crawford
In 1987, Richard Gere already had a resume of women he had dated, which listed, amongst others, Kim Basinger, Priscilla Presley, and a few other big names. He was the stud to end all studs. Stunning Cindy Crawford was only in her early twenties when she met Mr. Gere, which led to the two marrying in 1991.
Crawford didn't want to waste her precious twenties with the silver fox and decided to untie the knot. She was one of the hottest women alive during the 1990s, and he was, and still remains, a true charmer any woman would love to have.
Kim Basinger and Prince
The movie "Batman," which was screened in 1989, was where it all began for Kim Basinger and musician Prince. Basinger starred in the movie, while Prince was responsible for the amazing soundtrack. Kim Basinger was interviewed once, and she said very freely that the time with Prince was very meaningful for her, as all moments were back then.
She was a free spirit who did whatever was on her mind, and judging by Prince's public image, he was very similar to her in that respect. Apparently, dating Prince was right up her alley. The two even worked together on music projects!
Winona Ryder and Christian Slater
It is no surprise that this romantic story took its first steps on set. It happened to many stars, and it happened to Christian Slater and Winona Ryder too. Slater and Ryder starred together in the 1988 movie "Heathers" and had a massive crush on one another, so it's a good thing they played a couple.
They announced publicly that they were an item, even though their relationship didn't last too long. Winona Ryder said that Slater was just another story to add to her relationship book. Slater, however, admits that Winona was the love of his life and the woman he always wanted.
Reese Witherspoon and Ryan Phillippe
Where would we be without the ultimate '90s rollercoaster romance between Reese Witherspoon and Ryan Phillipe? The pair met when Ryan crashed Reese's birthday party. He turned out to be a very welcomed uninvited guest!
In 1999 they went on to star as doomed lovers in the cult classic "Cruel Intentions" and got hitched a few months later. After rumors and suspicions of Ryan allegedly playing around with other women, Phillipe and Witherspoon called it quits. They have two children together — a daughter named Ava and a son named Deacon, who they continue to happily co-parent to this day.
Brooke Sheilds and Liam Neeson
Despite their 13-year age gap, Brooke Sheilds and Liam Neeson hit it off in late 1991. Their love connection was so intense that Neeson popped the question after only 3 months of dating! However, shortly after the proposal, Liam flew home to deal with his home flooding.
Brooke apparently patiently waited to hear from her fiance but never did. Yep, he ghosted her! Even Brooke Shields can get ghosted, apparently. No one is safe anymore. A few months later, when he got his senses back, he came crawling back to her and re-proposed, to which Sheilds answered, "NO." Go, Brooke!
Lance Bass and Danielle Fishel
"Boy Meets World" star Danielle Fishel and NSYNC member Lance Bass were high school sweethearts back in the 90s and even went to prom together. The young lovers weren't meant to be but remained good friends. After Lance came out as gay in 2006, Danielle was incredibly supportive of her former flame.
Lance recently told Danielle, "I always knew you would completely accept me," on his podcast "The Daily Popcast with Lance Bass." Now that's love! The two eventually found romance in other partners — Bass is married to actor Michael Turchin and Fishel is married to film producer Jensen Karp.
Ellen DeGeneres and Anne Heche
Just mere days before Ellen DeGeneres's iconic "InStyle" magazine cover where she announced to the world that she was gay hit the stands, she met the late actress Anne Heche at the 1997 Vanity Fair Oscars Afterparty. It was an instant connection and very soon the two skyrocketed into being the most famous queer couple in Hollywood at the time.
Unfortunately, their relationship ended a few years later when Heche apparently left Ellen with no explanation. In a 2001 interview with the "Los Angeles Times," Ellen admitted, "I'm left with everybody else wondering what happened...I feel betrayed." Talk about being blindsided!
Matt Damon and Minnie Driver
1997 was a great year for Matt Damon. Not only was his critically acclaimed film "Good Will Hunting" released (for which he would later win an Academy Award for best screenplay) but he also found love.
Matt and Minnie met on the set of the film and started dating. However, any good will (pun absolutely intended) between the two fizzled out when Damon broke up with Minnie by announcing to the world that he was single on "Oprah." Millions of viewers, including Minnie herself, were shocked by the announcement! Not a cool move, Matt. We wonder what Luciana, his current wife, has to say about it.
Notorious B.I.G and Faith Evans
In a whirlwind romance, the iconic rapper, the late Notorious B.I.G. (also known as Biggie Smalls) met musician Faith Evans on the set of a photoshoot in 1994. A mere eight days later — yes eight days — the two were married! These two knew how to move quickly!
Reportedly, while the romantic relationship between the two began to fizzle out, they remained friends. They even welcomed a baby boy into the world in 1996. Unfortunately, the rapper never got to enjoy being a father for too long as he was killed a mere six months after his son's birth.
David Spade and Kristy Swanson
It is no secret that Spade is more celebrated for his humor and comedic work than he is for his physical appearance, but that has not stopped him from dating some of the most attractive women in the industry. In fact, the "Saturday Night Live" alum and comedian has a rather lengthy list of former flames.
One of the first on the list is actress Kirsty Swanson. Spade and Swanson met on the set of the 1996 film, "Heads in a Duffel Bag." With a title like that, it's no wonder the film bombed. However, love blossomed between the stars which lasted for almost a year.
Joaquin Phoenix and Liv Tyler
It seems that Live Tyler really believes in love at first sight! In an interview with "The Morning Call," Liv revealed that, "I fell in love with Joaquin the second I saw him" on set for the 1997 film "Inventing the Abbots." Sadly, their romance only lasted for three years until the pair split. It's alleged that Liv was more dedicated to the relationship than he was.
Whatever the case may be, they remain friends. According to Tyler she doesn't fall in love very often. She has, however, had two more serious relationships after Phoenix. Phoenix is currently in a relationship with actress Rooney Mara.
Ted Danson and Whoopi Goldberg
While on the set of the 1993 film, "Made in America," Ted Danson and Whoopi Goldberg started a romance that has since been dubbed "the affair that cost Danson $30 million." Quite the title. Ted Danson had been married to his wife Casey Coates for almost two decades when he and Whoopi ignited their surprising romance.
Once the secret was out, Coates filed for divorce which ultimately cost Danson a cool $30 million as well as a butchered reputation. After a year and a half, Whoopi and Ted called it quits in an anything-but-amicable breakup. Was it all worth it?
Michael Keaton and Courteney Cox
The year was 1989. Before Michael Keaton donned the Batman suit and before Courteney Cox was having coffee with her friends at Central Perk, the pair met and fell in love. After six years together, and rumored potential engagement, Keaton and Cox called it quits.
The two went their separate ways and got married — Cox married David Arquette and Keaton married Caroline McWilliams. While it's never been revealed what caused the breakup, Courteney admitted to "People" magazine in 1995 that "We still love each other." Considering they are both divorced now, could there ever be a comeback? We sure hope so.
Salma Hayek and Ed Norton
There are so many Hollywood couples who met while working together on one set or another. But apparently, there are more ways for celebrities to be introduced to each other. Who needs Cupid when you have a chiropractor? Yup, Hollywood royalty Selma Hayek and Edward Norton met through their mutual chiropractor in 1999!
Turns out he or she really had the couple's backs...Ha Ha Ha. The private pair dated for a few years until parting ways in 2003. While the cause of the split has never come to light, Hayek and Norton still seem amicable, even attending each other's weddings.
Thurston Moore and Kim Gordon
Thurston Moore and Kim Gordon were the ultimate romantic Rock and Roll royalty. The two musicians met, fell in love, and formed the iconic band Sonic Youth back in 1981. Moore and Gordon even tied the knot in 1984 making them the coolest married couple in the music industry at the time.
Unlike a love song, the rockers' relationship untimely turned very sour. It turned out that Thurston was secretly seeing his book editor Eva Pinz. Kim discovered the truth when she noticed suspicious texts on Thurston's phone. Sonic Youth imploded and the couple's relationship ended in a messy divorce.
Spike Jonze and Sofia Coppola
It seems that the band Sonic Youth was a hotspot for romance. Not only did former flames Thurston Moore and Kim Gordon form the band but directors Spike Jonze and Sofia Coppola met on the set of Sonic Youth's music video "100%."
What was first a formidable friendship soon blossomed into a romance that led the two to say their vows at Sofia's famous father's (Francis Ford Coppola's) vineyard in 1999. Sadly, Coppola and Jonze sadly split up a few years later. Some have even speculated that Sofia's film "Lost in Translation" drew inspiration from her strained relationship with Jonze.
Carson Daly and Jennifer Love Hewitt
If you were a TRL-loving teen, then you know all about the iconic relationship between MTV star Carson Daly and 90's actress Jennifer Love Hewitt, star of "I Know What You Did Last Summer." The two got together in 1998 and were so loved up that Daly went and got a tattoo of Jenniffer on his leg! Talk about a commitment.
As we all know, relationship tattoos often jinx a relationship. Carson and Jennifer called it quits. While the two remain good friends, Carson was shocked to discover the news of his break-up from "E! News" and not from Jennifer directly.
Fiona Apple and Paul Thomas Anderson
In 1997, songstress and indie music princess Fiona Apple and Director Paul Thomas Anderson were regarded as the ultimate 90s power couple. Not only was the pair a love match, but they collaborated on various projects together. Fiona lent her musical talent to Paul's film "Magnolia," while Paul directed four of Fiona's music videos.
What an idyllic portrait of the life of a couple of artists! Unfortunately, after four years, the relationship fizzled out. Fiona has since spoken out about the high pedestal the media put the relationship on and has revealed that the relationship had many negative and toxic elements.
Brad Pitt and Jennifer Aniston
Possibly THE It Couple of the 90s (and yes, the early 2000s) and America's sweethearts were, of course, Brad Pitt and Jennifer Aniston. One of the most famous celeb couples in Hollywood history began in a rather ordinary way. The pair was set up on a date by mutual friends. The rest was pop-culture history.
The end of Brad and Jennifer's marriage marked the beginning of a tabloid tsunami that would last years of rumors and gossip surrounding the failed romance. The two re-ignited rekindled romance rumors when spotted being very supportive of one another during the 2021 awards season.
Bruce Willis and Demi Moore
Talk about a whirlwind romance! Demi Moore and Bruce Willis first laid eyes on one another in July 1987 when... ahem... Demi was still involved with another man. She was engaged to Emilio Estevez at the time. It didn't take long for Demi to end her engagement with Estevez and jump head-first into a relationship with Bruce.
A mere five months after the first meeting, the two eloped in Las Vegas (how original). For a long time, they were one of the most high-profile couples in show business. However, After giving birth to three daughters and ten years of marriage, Moore and Willis divorced.
Gwen Stefani and Gavin Rossdale
In a burst of magical music match-making, Gwen Stefani's band, No Doubt, opened for Gavin Rossdale's band, Bush, in 1995. The songbirds quickly became love birds, and after a six-year relationship, the two got married! Sounds like a classic story. We're sure it can be made into a musical in a heartbeat. However, it didn't last.
Things seemed to be peachy for the pair, who then welcomed three children into the world. However, after it became apparent that Gavin was engaging in some...extra-marital activities with the family nanny...yawn... The two soon got divorced, and Gwen has since moved on with country crooner Blake Shelton.
David Bowie and Iman
One of the most successful showbiz couples has got to be David Bowie and Iman. While they had both been married, it seems that their love for each other was bigger than anything they had experienced before. The power pair were together for 26 years before Bowie's untimely passing.
The two first locked eyes on one another in 1990 at a dinner party. In an interview with "Hello Magazine," Bowie said, "My attraction to her was immediate and all-encompassing... That she would be my wife, in my head, was a done deal.” *Sniff* Can someone pass us the tissues, please?
David Copperfield and Claudia Schiffer
Some call it love, and some call it magic. Famous magician and illusionist David Copperfield managed to woo supermodel Claudia Schiffer by asking her for assistance during one of his shows in 1993. Would you look at that, apparently, magic tricks can, in fact, get you a girl! A year later, the two were engaged!
However, the engagement would never bloom into a marriage. The pair split up in 1999. What's particularly peculiar about the pairing is the controversy that surrounded it. Many have speculated that the relationship was a long ruse in order to boost Copperfield's fame. However, both Schiffer and Copperfield strongly deny this. Hmm...
Goldie Hawn and Kurt Russell
It's not unusual for co-stars to canoodle; however, what is unusual is for the canoodling to last for over 30 years. That happens to be the case for the loved-up pair Goldie Hawn and Kurt Russell. The two ignited their long-lasting relationship flame while on the set of the 1983 film "Swing Shift."
The two have welcomed a son named Wyatt as a sibling to Goldie's Kate and Oliver from her previous marriage to Bill Hudson. While all three children have the acting bug, it's pretty clear that Kate Hudson has garnered the most fame and success. When asked about the key to the pair's relationship success, Goldie credits the two for never marrying and having time to themselves.
Christie Brinkley and Billy Joel
In a meeting that would only be possible for the rich and famous, music icon Billy Joel and supermodel Christie Brinkley met while on a luxurious vacation in the Caribbean in 1983. How fancy! The piano man himself used his musical talents to woo his future wife.
Joel played the piano on the island where Brinkley and her group were vacationing, and the rest is history! It seems that the couple had a love for the sea as they tied the knot on a super yacht two years later. Sadly, due to busy schedules and failed communication, the pair divorced.
Pamela Anderson and Tommy-Lee
One of the most infamous couples of the 90s was undoubtedly Pamela Anderson and Tommy Lee. The two had a rather off-beat first encounter. After locking eyes at a New Year's Eve Party in 1994, Tommy Lee licked Pamela's face. Apparently, that swept her off her feet!
In what only can be described as a whirlwind romance, Tommy and Pamela were married only days later! Unfortunately, the pair's private love life became tabloid fodder which ultimately lead to their marriage breaking down. The two share two sons — Brandon and Dylan — both of whom are making their way in entertainment.
Hugh Grant and Elizabeth Hurley
As costars do, Hugh Grant and Elizabeth Hurley met and fell in love on the set of the 1987 film "Remando al Viento." The couple was together for an impressive 13 years (which may as well be 50 years in Hollywood time). If England hadn't already had actual royals, these two could definitely fill in that spot.
However, the relationship was far from perfect. Hugh was caught in a rather compromising position with a... let's call her a lady of the night... in 1995. Despite the shock and hurt on Hurley's part, the two stayed together for another five years before finally ending their relationship.
Melanie Griffith and Antonio Banderas
It's not surprising, given all the glamourous stars in attendance, that Hollywood award shows make for a great opportunity to meet your future lover. After all, that red carpet is right there and it's full of attractive people looking their absolute best. This was the case for Antonio Banderas and Melanie Griffith.
Banderas first saw Griffith at the 1989 Academy Awards and fell in love. Griffith was still married to Don Johnson at the time. It was only six years later, while co-starring in the 1995 film "Two Much", that the pair (who were...ahem...both married at the time) got together. Well, the pair lasted together until 2014, when they eventually split.
Jude Law and Sadie Frost
Before the tumultuous tabloid headlines surrounding Jude Law and Sienna Miller, there was Jude Law and Sadie Frost's relationship. Law and Frost met on the set of the film 1992 film "Shopping." While Frost was married to Gary Kemp at the time, she admitted in her biography "Crazy Days," "The force of the love I felt for Jude and his intense ambition made me feel out of control."
The two got together and eventually got hitched in 1997. Jude's career skyrocketed at the time, which added great strain on the already rocky relationship. Frost eventually filed for divorce in 20013.
Busy Phillips and Colin Hanks
Unlike most celebrity couples, Busy Phillips and Colin Hanks did not need the entertainment industry to put them together. There were no movie sets or award shows in their meeting story. The two met and started dating in college in 1997. The love between the two blossomed while they were both attending Marymount University.
Despite breaking up a few years later, the two have only had good things to say about one another over the years. The two remain such good friends that they've made several talk show appearances together over the years and their children (from separate relationships) even go to the same school!
Alec Baldwin and Kim Basinger
Ah, yet another loved-up co-star couple! Alec Baldwin and Kim Basinger met on the set of the 1990 film "The Marrying Man" and ignited their fiery relationship. As if the name of their film was a premonition for their future, Basinger and Baldwin were married a mere six weeks after first getting together.
Unfortunately, their love wasn't built to last. Basinger filed for divorce from Baldwin eight years after tying the knot. They famously have one daughter together — Ireland Baldwin, who has been enjoying quite an established career in the industry as a model, actress, and social media personality.
Chloe Sevigny and Harmony Korine
Ah, young love! Before Chloe Sevigny was an acclaimed actress and Harmony Korine a cult-classic director, the pair were just friends in their early teens. When it came time to cast actors for his first film, "Kids", Korine turned to Sevigny. Once the film was completed in 1994, the pair became more than just friends and co-workers.
Sevigny and Korine embarked on an on-again-off-again relationship that lasted several years but finally ended in the early 2000s. Since then, both of them have found true love — Sevigny is now married to an art gallery owner named Siniša Mačković, and Korine is married to former actress Rachel Simon.
Julia Roberts and Lyle Lovett
In a relationship that no one saw coming, Julia Roberts and Lyle Lovett had a whirlwind romance in 1993. The pair got hitched only three weeks after dating! Three weeks is usually enough time to finish a book (depending on the book) or go on a really fancy vacation. They are hardly enough time to decide you want to spend the rest of your life with a person.
The writing was on the wall when Lovett admitted in an interview with "People Magazine" that before tying the knot, "we’d never spent more than seven days together.” After two years of marriage, the relationship fizzled out and ended in divorce.
John Cusack and Jami Gertz
Back in the 1980s and 1990s, John Cusack set the standards for all men in the industry. Apparently, not only was he an inspiration for other men, but he was also very popular amongst women. Take Jami Gertz, for example. Gertz was a member of the famously known "Brat Pack" of the 1980s, and the two had things going around 1983.
They met on the set of "Sixteen Candles," and before it even began, the romance was already over. Cusack has since moved on to other relationships, though he has been extremely private about all of them, and Gertz went on to marry philanthropist Tony Ressler.
Jay Leno and Sharon Osbourne
Wait, what? Hasn't Sharon Osbourne been married to Ozzy since the dawn of time? Well, apparently she hasn't. Just like anyone else, she has her own history, though hers is arguably cooler than most. Before Sharon Osbourne was titled the First Lady of Rock&Roll, she had a short affair with Jay Leno.
Yes, THE Jay Leno. They met by coincidence at a bar and had a little fling. As it turns out, Osbourne didn't take the whole thing too seriously. Two months after they had their fling, Leno introduced his now-wife, the love of his life, to Osbourne, making the whole fling — history.
Chris O'Donnell and Reese Witherspoon
In 1993 Chris O'Donnell was 22 years old, and Reese Witherspoon was barely 16. She accompanied O'Donnell to a tribute party following his appearance in the movie "Scent of a Woman" and if anyone ever looked like the dictionary definition of the term "baby face", it has to be these two.
There was a bit more going on than just accompanying one another. Chris O'Donnell had reportedly admitted at the time that he had a soft spot for Whitherspoon and thought she was very nice. She, on the other hand, never spared a compliment and said that they were just friends.
Emilio Estevez and Paula Abdul
Emilio Estevez, known to most of us as the star of "The Breakfast Club" and "Young Guns," met Paula Abdul in 1991. They married just one year later, in 1992, and by 1994 the couple was already divorced. Well, that's the short version of it, at least. We are sure that each of them has a whole narrative to spill.
In one interview, Abdul said that their relationship ended because she wanted to have children. Emilio, who already had two children from a previous relationship, wasn't interested, leaving the two devastated and heartbroken. While she did get married after that, she has never had children.
Jennifer Garner and Scott Foley
Jennifer Garner met Scott Foley in 1998 when they were shooting "Felicity." Garner played Foley's girlfriend and, as so often happens for actors, ended up falling madly in love with him, for real. In 2000 they were married and, in 2003, divorced.
They both believe that their marriage never made it because they see themselves as "Hollywood victims." Everything is done in seventh gear, everything is instant and done in the heat of emotions, so it is not surprising that so many couples break up. Garner famously met her next husband, Ben Affleck, on a movie set too, and while their marriage lasted longer than her first, they eventually divorced.
John Cusack and Melissa Gilbert
In a turn of events, these two got involved in what looks like a classic game of jealousy, guilt, and emotional tugging. So, the little girl from the little prairie supposedly used Cusack to get back at Rob Lowe, who she dated for almost six years prior to bumping into Cusack.
Just one important detail: Lowe was Cusack's best friend at the time. She admitted this happened and excused it by saying that this was her own personal way of dealing with a broken heart and John just happened to be at the right time but in the wrong place.
Jennifer Love Hewitt and Will Friedle
When Jennifer Love Hewitt and Will Friedle were just 18 years old, they played best friends on the set of the movie "Trojan War", and we have a feeling you know where this is going to go but we will tell you anyway. The two kicked off a true love relationship from there on.
Later on, Hewit would play one of Friedle's love interests in "Boy Meets World." The relationship between the two on set was far more interesting than what was going on in reality, and the couple split up not long after they became publicly known as an item.
Denise Richards and Paul Walker
The late Paul Walker made it big when he starred in the movie "Tammy and the T-Rex" alongside Denise Richards. Now, he didn't succeed because of how great the movie was but because of what followed. He hit it off with one of the biggest names in the industry at that time.
Obviously, you can't just put these two beautiful creatures in the same room and NOT expect something to happen. These were the mid-1990s, and Denise Richards was one of the most beautiful and desirable women around. They were a ridiculously stunning couple who enjoyed the limelight for a good while.
Joey Lawrence and Keri Russell
Way before he became one of our most hated yet loved characters on "Felicity," Joey Lawrence was busy galavanting with Keri Russell down the streets of Hollywood. Their short relationship lasted for just under six months and had its share of drama.
As it turns out, while Russell was involved with Lawrence, she was still in an on-and-off relationship with the ex-boyfriend Tony Lucca of "The Mickey Mouse Club." The two have since tried their hand in marriage (to other people, of course), in divorce, and in parenting. Lawrence is currently married and Russell is in a relationship with another co-star, Matthew Rhys.
Fred Savage and Jennifer Love Hewitt
Fred Savage gained immense popularity in the late '80s and early '90s for his role as the lead in "The Wonder Years." At the same time, Hewitt was 14 and making a name for herself on Disney's "Kids Incorporated." The two young stars eventually crossed paths.
In an Instagram Live interview with TooFab, Hewitt reminisced about crushing on Savage. She revealed that for their first date, Savage took her to the Laugh Factory for a comedy show. Unfortunately, their love story was short-lived because of Hewitt's unusual pet: a pig. She said she never saw him again because he was really creeped out.
John Cusack and Lili Taylor
John Cusack and Lili Taylor starred together on "Say Anything." As it turns out, Taylor wasn't satisfied with only dating Cusack, as it was reported that she had a bit on the side with D.V. DeVincentis, one of Cusack's best friends at the time. Though they probably didn't stay friends after that.
In 2000 Taylor and Cusack starred together again, this time in the movie "High Fidelity." How ironic, considering how their previous relationship ended. The affair between the two never skyrocket, and maybe that's a good thing when you think about the uncomfortable events that made them go their separate ways in the first place.
Liam Neeson and Helen Mirren
This might come as a shock to you, but during the 1980s, the queen of the Oscars dated the king of the screen for almost five long years. Neeson and Mirren met playing the roles of Gawain and Morgana on the set of "Excalibur" when they were still both unknown.
They lived together, loved one another deeply, and admitted that, at the time, they were considered a serious item. Mirren confessed that the two broke up because Liam had difficulty being under Helen's shadow. If only he would have realized that such a great actor could never be under anyone's shadow.
Justin Timberlake and Fergie
Before NSYNC became NSYNC, the pop girl group Wild Orchid was a big thing, and Justin Timberlake and Fergie had it going. They were both in the entertainment industry from a young age, which is probably what drew them to one another. Timberlake was just 16 years old, and Fergie was seven years his senior. Age was never a barrier until Britney came along.
They have since both had high-profile relationships. Fergie married actor Josh Duhamel, had a son with him, and then the two got divorced. Timberlake is currently married to actress Jessica Biel, and they now share two kids.
Charlie Sheen and Robin Wright
Notoriously a bad boy, every single relationship that Charlie Sheen has been involved in reached the tabloids and the headlines. Except for one. Not much is known about his short affair with Robin Wright, and we are here to tell you all about it.
Sheen and Write had a sweet teenage romance that went on from 1981 until 1982. Sheen was 16, Write was 15, and they two were both in high school. This obviously explains why the press wasn't in on it when the two were an item. Since then, the two have dated many other Hollywood stars, enough to fill up another list.
Juliette Lewis and Brad Pitt
Before he became an A-lister, before his Hollywood royalty days, and before "Thelma and Louise," Pitt dated his co-star at the time, Juliette Lewis. She starred alongside him in "Too Young to Die?" and they were together for just over four years, despite a significant age difference between them.
In 1993 the couple decided to go their separate ways. They had an innocent love affair that would probably never survived if they would have met at an older age. Lewis married (and divorced) professional skateboarder Steve Berra, and Brad became Brad Pitt and had a lot of women to date.
Lisa Kudrow and Conan O'Brien
It is Conan O'Brien who we must thank for turning Lisa Kudrow into Lisa Kudrow (and Phoebe). As it turned out, Kudrow met O'Brien at an improv comedy class, and as soon as she set her eyes on him, she fell madly in love. Honestly, these two make such sense together that we're surprised we couldn't guess their history with each other.
The two dated for a while until they realized that a great sense of humor on both sides was not enough to keep the two together. O'Brien was the one who encouraged Kudrow to follow her dream and become an actress. And what a great job he did.
John Cusack and Janice Dickinson
The romance between John Cusack and Janice Dickinson was intensive and wild. Or, at least, that is what the papers said when they discovered the two were getting romantic with each other. The two were seeing each other a little after Cusack ended his story with Claire Forlani and before he had a short fling with Melissa Gilbert. What a busy guy.
It was reported that the two were caught while playing adult games in an airplane restroom. Hey, when they say "get a room" this isn't the kind of room they mean. Dickinson claimed that Cusack had no sense of humor and that she found him pretty dry.
Jessica Simpson and Jensen Ackles
Jenson Ackles was Jessica Simpson's first love and the first guy to give her a broken heart. In 1998, when Simpson was just 18 years old, she dated the "Supernatural" star, Jensen Ackles. Not long after, their romantic love affair in life would turn into a horror movie, for Simpson at least.
It took Simpson a long time to get over Ackles. The poor thing. On one episode of "Newlyweds," Simpson told her ex-husband Nick Lachey, that she was devastated after the breakup with her first love. She never mentioned the name, but it was obvious who she was referring to.
Jon Hamm and Jennifer Westfeldt
The love story between Jon Hamm and Jennifer Westfeldt began in the late 1990s and lasted almost two decades. They first met in 1997, way before Westfeldt starred in "Kissing Jessica Stein" and before Hamm found himself on the set of "Mad Men."
Jon was a party animal who enjoys the big and ravishing Hollywood parties, while Jennifer was the stay-at-home kind of girl, so they were destined to eventually go their separate ways. Really, people? You're together from 1997 to 2015 and THIS is the thing that finally comes between you? Anyway, Hamm is now engaged to actress Anna Osceola.
Robin Thicke and Paula Patton
We know that the love story between Robin Thicke and Paula Patton happened before either of them turned 20. We can only assume that what was going on between them was pure puppy love, but who would have believed these two were together for 21 years?
These were the early 1990s; they fell in love and were by each other's side through thick and thin. Or, shall we say, Thicke and thin? Until 2014 when they realized 21 years was more than enough. While we are unaware of any current partner Paula may have, Robin is currently seeing model April Love.