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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.

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