Celebs Who Used To Date But We Forgot About It

Sep 03, 2021James Montalvo

Hollywood may be the land of the stars but it's also the land of failed high-profile relationships. The sheer number of beautiful A-listers in proximity with each other makes it difficult to keep up with who's dating whom. With that in mind, we've decided to talk about celebrity couples that most people forgot were even a thing, to begin with. Here are a bunch of celebrities who use to date, that we forgot about.

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JOSH GROBAN & JANUARY JONES

January Jones kicks off this list. She's one of our few repeat offenders for this list. She dated singer Josh Groban from 2003 to 2006. As unlikely as this pairing may seem like today, the two were pretty serious together. As Groban tells it, it was his longest relationship ever back then. They made the usual red-carpet rounds but the love fizzled into nothing after two and a half years.

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JENNIFER ESPOSITO & BRADLEY COOPER

Jenifer Esposito is probably better known for her roles in television than for her films. The same could be said for Bradley Cooper if she hadn't landed The Hangover. Before his rise to superstardom, however, Cooper was with Esposito from 2006 to 2007. They dated, got hitched, and divorced in a span of a year. Their marriage only lasted four months, and tabloids described it as toxic.

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GWEN STEFANI & TONY KANAL

In more recent years, Gwen Stefani has made a name for herself in the world of television thanks to The Voice and her relationship with her co-judge, Blake Shelton. For now, we'll talk about her first long-term and serious relationship with her former bandmate, Tony Kanal. Kanal was their band's, No Doubt, bassist. They broke up while on tour and promoting their first album which was 'brutal' for both of them. The break up ended up as motivation for Stefani finding her solo career, and writing the 'Don't Speak.'

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KATE HUDSON & ALEX RODRIGUEZ

For only a few months in 2009, actress Kate Hudson dated baseball superstar Alex Rodriguez. To be frank, Rodriguez's list of past loves that can be considered high-profile deserves a list of its own. However, Hudson and Rodriguez got close enough to invite her step-dad, Kurt Russel, and mom Goldie Hawn out to watch one of his games.

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KATIE HOLMES & CHRIS KLEIN

Before Katie Holmes' dramatic and controversial marriage to Tom Cruise, she was dating a fellow young actor by the name of Chris Klein. The dreamy-eyed Klein is one of the stars of the American Pie franchise as well as We Were Soldiers with Mel Gibson. The two dated from 2000 to 2005. They even got engaged, but then Tom Cruise happened.

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TOM CRUISE & PENELOPE CRUZ

Speaking of Tom Cruise, he's on this list too. Before Katie Holmes, Cruise was tied up with another star who is also on the list, Penelope Cruz. The two actors met on the set of Vanilla Sky, and it's pretty obvious that sparks flew pretty quickly. I mean just look at that beautiful ex-couple. The relationship lasted until 2004, a little after that Cruise was jumping on Oprah's couch for Holmes.

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MILA KUNIS & MACAULAY CULKIN

Just when you think things couldn't get weirder, we'd like to remind you that Macaulay Culkin -- yes, the boy from Home Alone -- used to date, Mila Kunis. The Home Alone and the 'That 70s Show' star started dating in 2002 when Kunis was only 18 years old. They went steady for eight years before calling it quits. 

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JOHNNY DEPP & KATE MOSS

There's no surprise that on a list of romances from the past we see Johnny Depp. He dated international supermodel, Kate Moss from 1994-98. Sufficient to say that the pair, although collectively breath-taking, was doomed from the start. Depp's reputation for having difficult mood swings was the cause of this power-couple's downfall.

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BRAD PITT & GWYNETH PALTROW

Of course, Brad Pitt is on this list. But while the world is still reeling from his divorce from Angelina Jolie and is stunned by his new, hot German model girlfriend, let's take a trip down memory lane. From 1994-97, he was in a serious relationship with fellow actor, Gwyneth Paltrow. They met on the set of Se7en, and Brad even proposed. 

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RICHARD GERE & CINDY CRAWFORD

In the late-80s and early-90s, Richard Gere was one of the most sought after leading men in Hollywood. Naturally, he had a successful and beautiful woman that matched his stardom. This was none other than supermodel, Cindy Crawford. They were together from 1991-95, were married, and share a son. However, their seventeen year age gap and the fact that they were never friends, to begin with, kept things from lasting.

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EDWARD NORTON & SALMA HAYEK

Yes, you better believe it. Movie stars Salma Hayek and Edward Norton were once a couple. They even stayed together for almost five years. The actors were an item from 1999-03, and it's been reported that they were set up by their chiropractor. They even shared the screen in Hayek's Oscar-nominated biopic, Frida.

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UMA THURMAN & GARY OLDMAN

If you remember Gary Oldman being married to Uma Thurman, then we're pretty sure you were always caught up on celebrity gossip back in 1990 up to 1992. Back then, Uma Thurman was only eighteen when she fell head of heels in love for the now-great British actor. Their union was the actress' first marriage, both parties agreed it was a mistake

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RENEE ZELLWEGER AND JIM CARREY

For a brief spell at the turn of the millennium actors, Renee Zellweger and Jim Carrey had a romance. For them, days between 1999 to 2000 would be a rollercoaster of passion, love, and loss. They even got engaged, but for one reason or the other, it fell through. Carrey even calls Zellweger 'the great love of his life.'

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JENNIFER LOPEZ & P. DIDDY

When the 2000s came rolling in, there arguably wasn't a bigger couple in the music industry than Jennifer Lopez and P. Diddy. The rapper and music producer dated the Latin-American singer and actress from 1999 to 2001. Unfortunately, as you know by the title of this list, they didn't stay together. Lopez believes Diddy cheated, but there hasn't been any concrete proof of that made public.

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JENNIFER ANISTON & VINCE VAUGHN

The late-90s to early 2000s saw Jennifer Aniston rise from the world of television, to becoming one of the hottest names in Hollywood. Among her high-profile romances after being married to Brad Pitt was a run-in with actor and comedian, Vince Vaughn. From 2005-06, the two Hollywood stars dated, but the fact that they were always working tore them apart.

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CAMERON DIAZ & JUSTIN TIMBERLAKE

These days you probably can't picture Justin Timberlake being beside anyone other than his beautiful wife, Jessica Biel. But from 2003-06, the renowned pop & RnB singer was dating a different actress, Cameron Diaz. The two met at the Kids Choice Awards in 2003 when Diaz presented Justin with an award. 

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RYAN GOSLING & SANDRA BULLOCK

When we first saw this headline, we all went "really?" For some reason, a lot of folks have forgotten that, from 2001 to 2002, stars Ryan Gosling and Sandra Bullock were an item. Bullock was fresh from the success Ms. Congeniality, no doubt Gosling was smitten by it. But they in fact met on the set of 'Numbers' and began dating but split a few short years after.

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JULIA ROBERTS & KEIFER SUTHERLAND

When talking about whirlwind romances from the past, look no further than Julia Roberts and Kiefer Sutherland. Julia was an up and coming actress destined for stardom, and Sutherland was one of Hollywood's biggest bad boys. Sparks went flying when they met on the set of Flatliners. They dated from1990 to 1991 and culminated in Roberts leaving Sutherland on the altar.  

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HEATH LEDGER & NAOMI WATTS

How does one forget that at one time, two of Hollywood's hottest Australian imports got together? From 2002 to 2004, the ravaging beautiful Naomi Watts was swept off her feet by a young actor by the name of Heath Ledger. Watts was ready for a family, Ledger wasn't that was the end of them, but she wrote a touching piece on his passing in 2011.

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ASHTON KUTCHER & JANUARY JONES

Back when Ashton Kutcher was a young Hollywood heartthrob, he dated Mad Men's, January Jones. From 1998 to 2001, the two stars were an item. During that time, Jones was better known for being a supermodel and was exploring a career in acting when she and Kutcher were living together. It's been speculated that they split because Kutcher wasn't supportive of Jones' acting career.

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MATT DAMON & MINNIE DRIVER

Matt Damon and Minnie Driver were once Hollywood's promising young stars who just happened to be a couple. They met on the set of Good Will Hunting and started making public appearances in 1997. It's unclear why the two broke up, despite Driver being totally cool with the bromance between Damon and Ben Affleck. But Damon controversially announced the break up on Oprah, which Driver thought was "fantastically inappropriate.” 

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JENNIFER GARNER & SCOTT FOLEY

If you don't remember who Scott Foley is, that's okay. He hasn't been in many big projects in recent years. We won't forgive you, however, if you don't know who Jennifer Garner is. Anyway, these two met when they were young up and coming actors on Foley's tv show, Felicity.  Garner was a guest star. She would land Alias after that, and Hollywood took over. They were married from 2000-04.

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LEONARDO DICAPRIO & GISELE BUNDCHEN

I don't know about you, but it seems that Leo's countless flings with the world's most beautiful women tend to drown the fact that he and supermodel Gisele Bundchen were together for almost six years. Well, the two dated 1999-2005. The two were living the fast and high life that young celebrities tend to do. This took a toll on Giselle who wanted change, Leo didn't and that's that.

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ALANIS MORISSETTE & RYAN REYNOLDS

In the early 2000s, Ryan Reynolds was an up and coming actor, miles away from the Hollywood big-shot he is today. One thing remains the same though, that's his massive appeal to the ladies. From 2002 to 2005, the aspiring Hollywood actor dated recording artist, Alanis Morissette. They even found themselves engaged for three years, but as we know, it didn't work out.

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SARAH JESSICA PARKER & ROBERT DOWNEY JR.

One of the 80s' biggest bad boys turned out to be one of Hollywood's most profitable stars. You wouldn't have guessed it back then though as Robert Downey Jr. -- yes, Iron Man himself, was a bit of a troubled young star. From 1984 to 1991, RDJ was in an off and on relationship with Sarah Jessica Parker, the future star of Sex and the City. Unfortunately, he couldn't keep himself together to save their relationship.

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KIRSTEN DUNST & JAKE GYLLENHAAL

Back when Kirsten Dunst & Jake Gyllenhaal were an item, they were a couple of young and promising movie stars on the verge of superstardom. However, the difference in personalities that attracted the two stars to each other ended up being their downfall. The dated form 2002-04. They were a very tabloid heavy couple, and it was for a good reason. Just look them up in your free time.

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MATTHEW MCCONAUGHEY & PENELOPE CRUZ 

Once upon a time Matthew McConaughey and Penelope Cruz were an item. The two became co-stars in Shara, and that's where things got going. Naturally, when two beautiful actors are cast opposite each other you're gonna expect sparks to fly and they did between 2005 and 2006. However, it only lasted until the actor met his future wife while at a bar while still dating Cruz. I guess that's Hollywood for you.

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COURTNEY COX & MICHAEL KEATON 

Taking us back to the late-80s and early-90s is Courtney Cox and Michael Keaton. The two started dating the way a lot of celebrities started dating back before cellphones and sliding into DMs became something, they were introduced by a mutual friend. They dated for six years, keeping themselves out of the line of sight of tabloids for most of it, preferring to have dates at home. They were together from 1989 to 1995. 

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MADONNA & SEAN PENN

Finally, we have a pairing that will make you really wonder what was going on around the 80s. How did this become a thing at all? Sean Penn, yes the stoner dude from your favorite 80s teen movies was married to the Queen of Pop, Madonna. They were married from 1985 to 1989 but still, go on record saying they love each other to this day. 

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Was that a wild blast from the past or what? Did you ever know about these celebrity couples before reading about them now? Which one was the oddest pairing in your opinion? Let us know in the comment section and make sure to check out Amomedia for more great content like this.

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