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
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
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
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 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
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’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
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
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
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
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
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
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 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
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.