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Weird Celebrity Couples You Forgot Dated in the ‘90s and the ‘00s

Hands up if you forgot Ryan Reynolds and Alanis Morissette were a couple?!

    Unless you’re an emotionless robot who doesn’t have any concept of love or human emotion (same), there’s a high chance that adorable couples make your heart all warm and cozy. Yep, you feel the same tingly emotions when you see a cute puppy or eat a tub (or ten) of ice cream, and seeing other people happy just puts a spring in your step. These feelings get even more intense when you realize that your favorite celebrities are the ones that are in love. This is largely because we care more about these celebs than we do our actual lives, and because we love them with all of our hearts. Alas, they will never know how we truly feel. Unless you’re reading this, Mark Ruffalo, because we are completely and utterly in love with you.

    Over the course of Hollywood history, some of the coolest celeb couples have come out of the woodwork. There’s been Brad and Angelina, Beyonce and Jay-Z, Ellen DeGeneres and Portia De Rossi, Will Smith and Jada Pinkett Smith, and that’s just the start. But what if we told you that there have been some other celebrity couples that those in the limelight have “conveniently” forgotten about? Yuh-huh, it seems as though we’re not the only ones who pretend as though some relationships didn’t happen and some exes didn’t exist. These weird couples were totally legit, and they dated during the ‘90s and ‘00s. Prepare to cringe your ice cold heart out.

    Sandra Bullock and Matthew McConaughey

    Sandra Bullock and Matthew McConaughey were a couple in the 1990s

    Aw, weren’t these two the cutest?! Well, kinda. Sandra Bullock and Matthew McConaughey met on the set of “A Time To Kill” in 1996, and started dating pretty soon after. Unfortunately, it seems as though they didn’t have it in them to become the next Hollywood power couples, as their relationship didn’t seem to materialize into anything special. A year after their breakup, Sandra reported that Matthew was a “powerful force” in her life and that they had fabulous chemistry together. Errr, is that good?


    Madonna and Dennis Rodman

    Madonna and Dennis Rodman dated in 1994

    Remember the time when Madonna dated a basketball player? No, neither do we. Nevertheless, it totally happened, and we have this rather weird/iconic/odd photograph to prove it. Madonna and the infamous Dennis Rodman got together in 1994 and dated for a couple of months, and it seemed as though they were perfectly quirky for each other. The Queen of Pop once called her basketball bae “the Madonna of the NBA world,” but it only really seemed to be a fling. Slam-dunk.


    Gwyneth Paltrow and Brad Pitt

    Gwyneth Paltrow and Brad Pitt were together in the 90s and even got engaged

    These two blondies hit it off in the ‘90s, and it’s been reported that they shared everything. They shared love, they shared laughter, and they even shared their homes for a little while. They probably even shared their hair dye. Gwyneth and Brad got together in 1995, and even got engaged! Unfortunately, the wedding planning got called off in 1997, and they decided to separate. Every cloud has a silver lining though, because this breakup eventually led us closer to Brangelina.


    Julia Roberts and Kiefer Sutherland

    Julia Roberts and Kiefer Sutherland were dating in the 1990s

    Julia Roberts and Kiefer Sutherland dated when Julia was at the peak of her Hollywood presence and fame (which, to be honest, has been ongoing since the dawn of time). The two of them dated in the ‘90s and were even engaged to be married. They spent months planning the most romantic wedding and Kiefer couldn’t wait to be her husband. However, a few days before her wedding, Julia Roberts was a literal Runaway Bride and ran off with Sutherland’s friend, Jason Patric. Yikes.


    Winona Ryder and Matt Damon

    Winona Ryder and Matt Damon were a couple for a brief time in the 90s

    We’re so sad this relationship didn’t pan out. The two famous stars of Hollywood began dating each other after they were introduced to each other by Gwyneth Paltrow (it’s a small world when you’re rich and famous) and hit it off straight away. Winona Ryder and Matt Damon only really dated for a year, which is a shame, because they would have made the most beautiful babies. We can still pretend that they had something super special though, right? You know, to put a smile on our faces?


    Ashton Kutcher and Brittany Murphy

    Ashton Kutcher and Brittany Murphy were an item in 2003

    Ashton Kutcher and Brittany Murphy’s relationship was a match made in Hollywood. Quite literally. These two iconic actors met on the set of Just Married in 2003, where they were roped in to play a married couple. It seems as though they took their method acting to the next level when the cameras were turned off, as they later got close in real life. So close, in fact, that there were rumors they were even engaged off set. Sadly, their relationship only lasted a couple of months.


    Cameron Diaz and Matt Dillon

    Cameron Diaz and Matt Dillon dated for three years in the 90s/00s

    You probably remember Cameron Diaz and Matt Dillon from the hilariously funny movie, There’s Something About Mary. Sure, Dillon plays a stalker, but who cares? At the time of filming, these two were actually dating and had been for three years. They seemed like the perfect couple, and everyone thought they would be the new Goldie Hawn and Kurt Russell (AKA ultimate legends). Unfortunately, they ended things just after they called wraps on filming. Perhaps it was the stalking thing that kinda freaked her out. Makes sense.


    Matthew McConaughey and Janet Jackson

    Matthew McConaughey and Janet Jackson were a short lived couple in 2002

    Would you ever believe these two were actually an item? The King of Hollywood and the Queen of pop? Quite possibly the oddest combination of people. Like, ever. But yep, this really did happen, and we have the pictures to prove it. They dated for a few months in 2002, but it seems as though this match just wasn’t meant to be. They ended things soon after, and if Matthew didn’t sing “Sorry Ms. Jackson, oooh, this love isn’t for reaaaaaaaal,” then he seriously missed out on a trick there.


    Courtney Love and Ed Norton

    Courtney Love and Ed Norton dated for three years from 1996 until 1999

    And the award for the most random relationship in the history of celeb couples goes to….Courtney Love and Ed Norton! Hurrah! Three cheers for these guys! This pair started dating in 1996 after appearing in The People vs. Larry Flynt, and it seems as though they hit it off straight away. Their relationship soon ramped up a notch as Ed later popped the question, and they even made preparations for their wedding. They were engaged for six months and together for three years before they eventually broke up in 1999. Weird.


    Julia Roberts and Benjamin Bratt

    Julia Roberts and Benjamin Bratt dated for four years

    Because we love Julia Roberts so much, we had to write about her twice. We feel like anything less would be a disservice to her. We also have to write about her twice because her taste in men has always been a little questionable. No offense. Although Julia Roberts and Benjamin Bratt looked like a picture postcard, their work schedules made their four-year relationship a strain, and they eventually parted ways. Four years is a long time, man. How did we forget about these guys?


    Ellen DeGeneres and Anne Heche

    Ellen DeGeneres and Anne Heche were together during the 1990s

    If you don’t remember these two together, simply Google ‘Ellen DeGeneres and Anne Heche + Red Carpet’ and we’re sure the memories will come flooding back. These two rocked the red carpet and coordinated their outfits, their eyewear, and their hair. Genius. This relationship is even more memorable because this was Ellen’s first LGBT relationship since she publicly came out in 1997. Although we’re sad they broke up, we have three words for you: Portia De Rossi.


    Lance Armstrong and Ashley Olsen

    Lance Armstrong and Ashley Olsen dated in 2007

    Okay, we really, really, really wish we remember this happening, because it sounds like we may have been having a nightmare. Professional cyclist Lance Armstrong dated former child-star and one-half of the Olsen sisters, Ashley Olsen back in 2007. This was just after he’d split from Tory Burch, but their odd relationship didn’t last long. Their little love affair came to an end when Lance was urged to ditch Ashley to protect his image. It turns out that his fans weren’t happy about their 15-year age gap…


    January Jones and Ashton Kutcher

    January Jones and Ashton Kutcher dated from 1998 until 2001

    January Jones and Ashton Kutcher dated from 1998 until 2001 when she was just an Abercrombie and Fitch model trying to make it in the acting world. I mean, what a winner for both of them, am I right? But it seems their relationship was cut short because Ashton had no faith in her acting and told her she wasn’t going to make it in Hollywood. Okay, maybe that wasn’t such a winner for her. That was actually kinda harsh. Well, she sure showed him.


    Alyssa Milano and David Arquette

    Alyssa Milano and David Arquette dated in 1991

    Nowadays, we know David Arquette for his 14-year marriage to Courteney Cox, but did you know that he also dated this former child star? Alyssa Milano and David Arquette had a brief fling in 1991, but it ended pretty quickly. The Who’s The Boss? star and the popular actor and filmmaker had pretty hectic schedules and had their eyes on other people. Well that must have been pretty awkward. At least try and hide your wandering eyes, guys.


    Minnie Driver and Matt Damon

    Minnie Driver and Matt Damon dated in 1996 for a year

    Weren’t these two just the cutest? Their relationship didn’t start on the school playground. Instead, their love blossomed on the set of Good Will Hunting. They first started dating in 1996 and were together for a year before Matt Damon did the unthinkable. Without talking to his ‘girlfriend’ or ending things in person, he went on Oprah and announced it to the world. Not cool, Matt Damon.


    Ryan Gosling and Sandra Bullock

    Ryan Gosling and Sandra Bullock were a couple in the early 00s

    Okay, how did we ever forget that these two were a couple?! These two are the greatest. But their relationship was pretty weird. Sandra and Ryan dated back in the early ‘00s and get this… he was 21, and she was 37! Who knew Sandra was a cougar? Despite the fact they look amazing together, their relationship eventually ended, and Ryan went on to have major #RelationshipGoals with Eva Mendes. Yep, we kinda want to be them.


    Courteney Cox and Michael Keaton

    Courteney Cox and Michael Keaton dated for 5 years from 1990

    It’s hard to imagine Courteney Cox without Chandler Bing by her side, but you’ve probably forgotten that this Friends actress and the guitarist for Snow Patrol started dating in 1990 and dated for five years! Friends close to the pair often said that the spark between them was undeniable, but the relationship broke down after Courteney was linked with fellow Friends star, Matthew Perry.


    Mariah Carey and Derek Jeter

    Mariah Carey and Derek Jeter dated in 1996 for nearly 2 years

    It’s hard to think of Mariah Carey with someone other than Nick Cannon, but it seems as though that ship wasn’t always sailing in the Mariah marina. Mariah hooked up with Yankee star, Derek Jeter, in 1996 and dated for nearly two years. In the end, the two found the media pressure surrounding their relationship too much, and decided to part ways. They have been friends ever since, because who doesn’t want to be besties with Carey?


    Sarah Jessica Parker and Robert Downey Jr.

    Sarah Jessica Parker and Robert Downey Jr. were a couple in the early 90s

    What do you get if you mix a SATC star with Iron Man? Well, Sarah Jessica Parker and Robert Downey Jr.’s relationship. The two of them dated back in the early ‘90s but sadly broke up because of Robert’s notorious narcotics problem. Which, in hindsight, is probably for the best. After all, who would want to see Iron Man going shopping with the closet queen standing next to him? Not us. That’s so not his style.


    John Mayer and Taylor Swift

    John Mayer and Taylor Swift were a couple in the late 00s

    John Mayer and Taylor Swift were the sweethearts of the late ‘00s. We could just imagine them having romantic dinner together, singing country songs and serenading each other. I mean, that’s what singers do all the time, right? But sadly, these lovebirds’ schedules kept them apart, and they ended their relationship in 2010. But it didn’t end well, with Mayer since cursing the day she was born. Right…


    Madonna and Vanilla Ice

    Madonna and Vanilla Ice dated in the 90s

    Okay, how do we not remember this happened?! Ice Ice, Baby. Back in 1990, Madonna and Vanilla Ice mixed together to create one pop/rap concoction, and were were kinda here for it. After all, they dated in the only way Madonna and Vanilla Ice could. Their relationship was fuelled by narcotics, alcohol, partying and (ahem) physical encounters. Unfortunately, their relationship came to an end after Madonna published her book which featured pictures of Ice without any clothes on.


    Rachel Wood and Marilyn Manson

    Rachel Wood and Marilyn Manson were a couple for 3 years

    We have to give credit to anyone who decides to date, Marilyn Manson. We’re sure he’s a great guy, but we just couldn’t risk him stealing our eyeliner all the time. Nevertheless, Rachel Wood obviously had more patience than we could ever have, as she and Marilyn Manson had a pretty solid relationship in Hollywood terms. They dated and were engaged for three years before it all came crumbling down.


    Quentin Tarantino and Margaret Cho

    Quentin Tarantino and Margaret Cho dated in the 1990s

    It’s hard to think of hard-nosed Tarantino with a hilarious comedienne, but anything and everything seemed to happen in the ‘90s. These two met after Quentin was roped in to direct an episode of ‘All American Girl,’ which just so happened to be Cho’s show. They hit it off from there but broke things off after a couple of months. Ah, the world could have been so different if they had stayed together.


    Whoopi Goldberg and Ted Danson

    Whoopi Goldberg and Ted Danson had an affair in the 90s

    If you don’t remember Whoopi Goldberg and Ted Danson as a couple, you might remember the scandal surrounding The Good Place star. Ted and Whoopi started having an affair while he was still married with his wife and came into the public eye when he suffered from a pretty public $30 million divorce. They eventually carried on their relationship…until they split up in 1993, just one year after the divorce proceedings. Ted would definitely get into the Bad Place for that.


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