Celeb Relationships From The ’90s We’re Still Not Over

Another day, another celebrity breakup.

And each time we can’t help but say to ourselves, “Well that’s it, love is dead.” I mean if it can’t work for famous stars, what hope is there for the rest of us? (Good news, still lots of hope.)

However, we still remember the shock of the great Brad Pitt and Jennifer Aniston’s split of 2005, the Ben Affleck and Jennifer Garner divorce of 2018, and most recently we have been grieving Miley Cyrus and Liam Hemsworth’s separation. Though, honestly we’re still hoping they find there way back to each other.

So many breakups seem to shake us to our very core, and make us doubt our beliefs about relationships in general. But, we have to admit, the real peak of the celebrity mega couple, and subsequent breakup was the ’90s.

Ah, the 1990’s – the decade was filled with butterfly clips, baggy pants, and a number of other ridiculous fashion choices. Though somehow, even more outrageous than the clothing choices, were the A-list relationships. Seriously, some of the couples during that time we had NO idea ever dated, while others simple made us drop our jaws to the floor.

In hindsight, a lot of these couples don’t make sense, but that doesn’t mean they weren’t special or deserved to be remembered. After all, we all know you have to kiss a lot of frogs before you find your Prince Charming. And let’s just say Hollywood is filled with a lot of the same frogs.

Let’s take a look back on famous couples from the ’90s, and the breakups we may have seen coming.

Brad Pitt and Gwyneth Paltrow

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Before there was Brad and Jen, there was Brad and Gwyn.

The couple pretty much defined the ’90s power couple after meeting on the set of Se7en in 1994. The couple was almost as successful as the movie and it wasn’t long before they were serious. Brad even referred to her as the “love of my life” in his Golden Globes speech. Yikes. The couple was together for roughly three years before breaking up in 1997.

It also recently came out that during their relationship Brad had spoken up to Harvey Weinstein, who had made unwanted passes at Gwyneth.

While they didn’t technically didn’t meet in the 1990’s, the couple would end up being together for the entire decade. They met at Kidman’s audition for Days of Thunder in 1989, and were married just one year later. They also during the course of their relationship made three movies together (including one with Stanley Kubrick that almost tore them apart,) and adopted two children. Their love didn’t make it far into the new millennium and they got divorced in 2001. After they split, Cruises relationship with the Church of Scientology became tabloid fodder for the reason they broke up, but its never been confirmed.

Sarah Jessica Parker and Robert Downey Jr.

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One of the first couples of the early ’90s to fall.

When you think of Sarah Jessica Parker, now, it’s hard to imagine her with anyone other than Matthew Broderick. It’s also hard to picture Robert Downey Jr. before he became the behemoth character of Iron Man. But the ’80s and ’90s were a different time.

The two met on the set of Firstborn and stayed together for seven years, also known as an eternity in Hollywood.

Unfortunately, their relationship came at the height of Downey Jr.’s drug addictions, and Parker has been open about it leading to their split.

In an interview with Vanity Fair she reflected on the relationship saying, “There was a huge amount of time spent making sure he was ok. At a certain point, I had the courage to say, ‘I’m going to walk away, and I’m just going to pray that you don’t die.'” Luckily, both parties went on the lead happy and successful lives following the traumatic split.

Jennifer Lopez and Sean “Diddy” Combs

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Who could forget “the dress?”

When Jennifer Lopez started dating Sean Combs in 1999, they quickly transformed into JLO and Puff Daddy. (Could there really be a more ’90s name for a couple?) The pair met while Lopez was recording her first album. Not only did their romance rock the music industry, it also rocked the fashion world. Each time the couple appeared on a red carpet they turned heads. Sometimes while wearing matching bandanas. Sadly, they broke up in 2001, partly due to his infidelity, according to Lopez.

Tobey Maguire and Rashida Jones

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Wait, what?

Yes. In one of the most surprising couples of all time, many forget that Rashida Jones and Tobey Maguire dated. It was right before their careers really took off. They even got engaged. Weird to think that Spider-Man and Ann Perkins could have been a couple. The pair split right before Maguire landed the coveted role in Sam Raimi’s Spider-Man after dating for three years.

Winona Ryder and Johnny Depp

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Name a more ’90s couple. I’ll wait.

Johnny Depp and Winona Ryder were powerhouse stars in their own right when they got together in 1989. The two met at a premiere of Great Balls Of Fire! Their romance was a complete whirlwind, and they even got engaged after only five months of dating. Plus, a few of us still remember the “Winona Forever” tattoo that Depp got on his arm. Though they never married, Depp and Ryder were engaged for the duration of their three year relationship.

They even co-starred in the classic Tim Burton film Edward Scissorhands.

After they broke up in 1993, and called their engagement off, hearts around the world mourned the loss of their favorite grunge couple. Years later, Ryder said in an interview with Elle that Depp was her first real heartbreak. “I had just done Dracula and Edward Scissorhands. And I think it was really ironic because like everybody else just thought I had like everything in the world, you know, I had no reason to be depressed, everything was sort of at its peak, but inside I was completely lost.”

Elizabeth Hurley and Hugh Grant

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Their cheating scandal that rocked the world.

To say Hugh Grant and Elizabeth Hurley were an iconic couple of the ’90s is an understatement. Grant had just solidified his status as the charming British bad-boy, (We’re still swooning over him honestly) and Elizabeth Hurley was a model, and one of the most beautiful women in the world. The two met on the set of a Spanish film in 1987, and the pair quickly became Hollywood royalty.

Then, everything came to an (almost) screeching halt in 1995.

The couple had been together for eight years when it was revealed Grant was caught with “a known prostitute” named Divine Brown. The story was one of the biggest scandals the industry had ever seen, and many thought it might be the end of Grant’s career, let alone his relationship. Shockingly, neither happened. Grant’s career continued to skyrocket, and Hurley managed to forgive him. The two remained together for another five years before splitting for good in 2000. The pair remain best friends with each other to this day. Must be true love.

Jennifer Aniston and Tate Donovan

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Turns out there might be something more awkward than a breakup.

Jennifer Aniston has had her fair share of high profile relationships. But, one that has flown surprisingly under the radar is her romance with actor Tate Donovan. The duo was introduced by mutual friends in 1995, just one year after a little show called Friends premiered. The pair dated for a couple of years, and Donovan would even surprise her with romantic gifts

He even bought her a puppy for Valentine’s Day.

Apparently Aniston walked into her dressing room and Donovan had put a puppy with a ribbon sitting in it. We don’t know about you but that sounds like the most romantic surprise ever. (Someone buy us a puppy please.) It seemed like the two were heading for wedded bliss. But sadly, reportedly her fame started to make him uncomfortable.

He never wanted to be that much in the public eye.

At the time Donovan even told People magazine, “Literally, our second date, there were video cameras everywhere, and I was like, ‘I’m out of here.'” However, Aniston was the one who finally broke things off, and she did it just a few weeks before he was set to guest star on Friends. After breakup up in the real life, the pair had to meet, fall in love, and break up again. This time though, it was all onscreen. Talk about a rough coping mechanism.

Reese Witherspoon and Ryan Phillippe

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We’re still not over this breakup. *Sigh*

After meeting on the set of Cruel Intentions, it wasn’t long before Reese Witherspoon and Ryan Phillippe became Hollywood’s new “It” couple. The pair seemed destined for endgame and dated for two years before they got married. They also would have two kids together, Ava and Deacon. However, they ended up divorcing in 2006.

What went wrong?

According to Reese, it was a lot to do with age. When asked about timing she said while she was happy with the way things turned out, she encourages other women to wait a little longer. “I got married when I was 23, and I had two kids by the time I was 27,” she said. “I don’t know, sometimes it’s good to know yourself [first].” Luckily, both Witherspoon and Phillippe remained friends and committed co-parents.

Cameron Diaz and Matt Dillon

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There’s just something about Cameron.

Cameron Diaz was undeniably one of the biggest starlets of the ’90s. She had transitioned from model to successful actress with films like The Mask, and My Best Friend’s Wedding. While her career was taking off, she began dating actor Matt Dillon. They met while both filming projects in Minnesota. (We’re guessing the super low temperatures make for the perfect cuddling atmosphere.) They dated for about three years before Diaz broke it off after filming their movie, There’s Something About Mary. Dillon has hinted it’s because he was ready to settle down, and she wasn’t.

Ellen Degeneres and Anne Heche

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Heche entered her first openly gay relationship with the famed comedian.

The couple met at a Vanity Fair Oscar’s party and immediately hit it off. The year was 1997, and Heche had just traveled the awards circuit for her movie with Al Pacino, and Degeneres was still starring in her own prime-time show. The pair became somewhat official after they were spotted getting close at President Bill Clinton’s White House Correspondence Dinner. The pair dated for three years before calling it quits in a rather messy breakup. Reportedly, Heche blames Degeneres for derailing her career, and the talk show host has banned her from the show. Seems like all is fair in love and war?

Matt Damon and Minnie Driver

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Wait, they dated?

Turns out, Matt Damon wasn’t sure either. At least that’s not the impression he gave on Oprah. Let’s go back to the beginning. They met on the set on Damon’s breakout film, Good Will Hunting, where Driver starred as his love interest. Soon life imitated art, and the pair began dating offscreen as well. However, they weren’t together for long, and broke up in 1998. At least, that’s what Damon said.

When asked if he was single on Oprah’s talk show, he said yes.

And Driver had no idea. Driver spoke about the breakup in an interview with the Los Angeles Times saying, “It’s horrendous breaking up with someone anyone, but to have it be so public and to be cast in a role that I would never play if they were paying me-this wronged worm! It’s unfortunate.” Well, safe to say when these two separated, it was for good.

Ben Affleck and Gwyneth Paltrow

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Like his best friend and co-star Matt Damon, Ben Affleck had his share of high-profile breakups.

After her relationship ended with Brad Pitt, and future husband Chris Martin was still ways away, Gwyneth Paltrow dated Ben Affleck. It’s hard to tell whether the relationship was ever serious, though they were off and on a lot. But it is rumored they had talked about marriage and settling down. In fact, that’s a big reason Paltrow says they split.

She recently went onto Howard Stern and opened up about her time with Affleck.

According to Paltrow, she didn’t think Affleck was in a good place to have a girlfriend at the time, despite them dating for three years between 1997 and 2000. “I think that when you’re in your twenties, you can get swept up in [good looks],” she said. “When you’re a kid, you tend to be more shallow and you’re also immature, so you think that being with a good looking person validates yourself in some kind of way. It’s not true.”

Justin Timberlake and Fergie

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They dated before Britney? Whoa.

Seriously. A few years before Britney Spears and Justin Timberlake became the golden couple of pop music, Timberlake was wooing another pop princess, Fergie. It was back in 1997, and the pair met because Fergie’s friend was dating J.C. Chasez. (Talk about a #TBT.) According to Fergie, the relationship was never serious and he was “Mr. Right Now.” Though they did apparently take a steamy vacation to Hawaii together.

Johnny Depp and Kate Moss

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After Winona, came Kate.

While Johnny Depp had no shortage of flings after breaking up with fiancee Winona Ryder, his next serious relationship was super model Kate Moss. The two met in 1994, at Cafe Tabac in New York City, a famous hangout at the time for the rich and mega-famous. He was 31, she was only 20. But their relationship lasted four years, and was nothing short of extravagant.

Ah, young love?

According to Moss, the actor would often present her with lavish and over-the-top gifts. This included a diamond necklace that was “hidden down the crack of his ass.” He also once filled a bathtub with $1,000 of champagne in a West London hotel. However, the two parted, partially due to Depp’s rampant mood swings. Though Moss still speaks fondly of the romance.

Courtney Love and Edward Norton

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And the award for most unlikely couple of the ’90s goes to…?

Believe it or not, Courtney Love and Edward Norton dated for four years between 1995 and 1999. The pair were so serious they even got engaged. (Yes, we can’t understand why no one is talking about this either.) Reportedly, their relationship was very volatile and often filled with intense fighting. Though the relationship has ended, their fighting has not. Love still talks about Norton on Twitter.

Bruce Willis and Demi Moore

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The marriage that defined the decade.

While most ’90s relationships are a long forgotten memory, everyone remembers the era of Demi Moore and Bruce Willis. The couple met at a screening in 1987 for the movie Stakeout, and immediately hit it off. They got so close, so quickly, that they wed four months later. Their whirlwind romance however, wasn’t short lived. They were married until 1998, and had three children together Rumer, Scout, and Tallulah.

They also have nailed the amicable exes thing, they often hung out with each others new loves (*cough* Ashton Kutcher *cough*) and have remained on friendly terms.

Joaquin Phoenix and Liv Tyler

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There’s almost nothing as powerful as a first love.

Joaquin Phoenix and Live Tyler were just starting out their careers when they met in 1995. They were only in their late teens and found each other an important transition time in their lives, and both have referred to the other as a “first love.” The pair dated for three years, and even starred in Inventing the Abbotts. Though their relationship ran its course early, the two remained friends, and their families still hangout! When asked about Tyler he said, “She’s a darling. I’ve said it over and over again. When Liv and I met, it was for a reason — I really needed her and she really needed me.”

Dennis Rodman and Madonna

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Some love stories are short, and some are barely a sentence.

Dennis Rodman and Madonna have both been linked to their fair share of celebrities. But the ’90s were a magical, simpler, time when it seemed like the most random of stars were falling in love with each other. This was the brief time when Rodman and Madonna were an item. They got together in 1994, and only lasted for two short months, albeit a very public two months. They were photographed everywhere, and many basketball fans blamed Madonna for being a distraction during the NBA Playoffs.