20 Hollywood Couples We Wish Were Still A Thing

If there's one thing us hopeless romantics want to believe in it's that 'happily ever after'. That's why it's so hard when the universe crushes our hopes by repeatedly tearing our favorite celebrity couples apart like it's no big deal.

Today we've assembled a list of the ones we mourn the most, those couples who made us believe that true love is invincible, only to leave us thinking the world is a cruel place where no good thing lasts long.

From iconic '90s couples like Winona Ryder and Johnny Depp, over everyone's favorite denim duo Britney Spears and Justin Timberlake, to Hollywood's greatest looking love story Angelina Jolie and Brad Pitt—we got them all. Honestly, this list is definitely not for the weak-hearted, and we advise everyone to have some tissues ready—just in case emotions take over.

At the end of the day it seems as if no matter how rich and famous one is, there is no guarantee that a relationship will work out. And seeing celebrities struggle the same way we do is definitely a reminder that these perfect human beings we adore so much are, in reality, just regular people like the rest of us.

Here they are, 20 of our favorite celebrity couples whose unions now, unfortunately, rest in peace.

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20 Angelina Jolie And Brad Pitt

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Alright, we're kicking the list off with a bang: Brangelina was probably the most iconic Hollywood couple of our time. Sure, we loved Brad with Jennifer too, but once the suavest guy in Hollywood made a movie with the most gorgeous lady in the game, all of us were shipping them.

Anyone who saw Mr. & Mrs. Smith could immediately see that there was real-life chemistry between the two actors, and as we know now—the rest was history. So while the two have been together pretty much since then, they only got married in 2014. Two years after that they separated and their divorce was finalized this year. If these two perfect human beings couldn't make it, then what does that mean for the rest of us?

19 Vanessa Hudgens And Zac Efron

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For most millennials, High School Musical was a classic that brought them straight back to their early teens. So naturally, once we found out that Gabriella and Troy were also a thing off-set, we were absolutely thrilled to see this couple flourish. The two dated for five years, but in 2010 they decided to go their separate ways.

Personally, we think that a High School Musical reunion movie needs to happen—we would like to see what our favorite Wildcats are up to after college! And who knows, maybe being on the set together again could rekindle things between these two...

18 Jennifer Lopez And Sean Combs — Aka Puff Diddy At The Time

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Back in the late '90s and early 2000s, J.Lo and Puff Diddy were one of the coolest couples in the music industry. She was just becoming big after the release of her debut album On the 6, and Puff Daddy was trying to figure out what to change his name to. Jokes aside, we think these two were a gorgeous couple, and it's a bummer they couldn't make it work.

As we know, both have moved on—Jenny from the block is currently engaged to former baseball star Alex Rodriguez, and Puff Daddy has, according to Time Magazine, decided to stick to the name Love—we're not kidding.

17 Rachel McAdams And Ryan Gosling

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The Notebook—AKA one of the best romance movies of all time—managed to have us shook to our core, dehydrated from all the crying, and hopeful that one day we would find our Noah (or Allie). And while we were too preoccupied reading all of Nicholas Sparks' books, the two leads hit it off and started appearing together publicly.

Rachel and Ryan were an on-and-off thing from 2005 to 2008, and while both of them are currently in happy relationships, we are lowkey hoping that one day Noah and Allie will reunite, and the world will finally be a safe and peaceful place to live again.

16 Winona Ryder And Johnny Depp

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Now let's go back to a couple that was probably the coolest thing that happened to the '90s—the pairing of Winona Ryder and Johnny Depp. Neither one of them was the classic Hollywood-like star the industry was so fond of, and both of them had this slightly mysterious and twisted vibe.

Regardless, the two were huge stars at the time—perhaps even because they were slightly unusual. They met in 1989, and by 1990 they were already engaged. Unfortunately, after three years they split—but hey, at least we've got these grungy-cool photos to admire! After all, we '90s babies missed this one. How we lament it!

15 Britney Spears And Justin Timberlake

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If you thought Winona and Johnny were a vibe, think again—because teen stars Britney Spears and Justin Timberlake were definitely what dreams were made of in the early 2000s. And let us tell you, the dreams (or rather nightmares) were made of denim.

The two dated for approximately three years, but when Justin released "Cry Me a River" in late 2002, we all knew Britney and Justin were a thing of the past. The video featured a very obvious Britney look-alike and the storyline implied she had done him wrong. Well, at least we won't get to see any more full-on denim looks from these two...

14 Jennifer Garner And Ben Affleck

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We still can't believe Bennifer vol. II is not a thing anymore. A quick recap for anyone who doesn't remember: Ben Affleck used to date Jennifer Lopez for 18 months in the early 2000s—a period we have Gigli, one of the worst rated movies ever, to thank for.

Either way, in mid-2004 Ben started dating actress Jennifer Garner, with whom he has three adorable kids. Unfortunately, in 2015 the couple announced their separation, and with that, the second Bennifer was a thing of history as well. Maybe Ben's third Jennifer will be the one. After all, they do say the third time's the charm!

13 Helena Bonham Carter And Tim Burton

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Helena Bonham Carter and Tim Burton were one of the biggest power couples of the 2000s, with working together on movies such as Corpse Bride, Charlie and the Chocolate Factory, Alice in Wonderland and Dark Shadows, and plenty others. The couple has two children together, but after over twelve years of being pretty much inseparable, Helena and Tim decided to call it quits in 2014.

While we are incredibly sad that this iconic couple couldn't figure their differences out, we are also miserable because we probably won't get to see them work on movies together anytime soon, either. It's a loss for love and a loss for film!

12 Reese Witherspoon And Ryan Phillippe

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Here's another couple we definitely thought would last forever. Unfortunately, the world is a harsh place where nothing is ever safe—and neither were Reese Witherspoon and Ryan Phillippe. According to IMDB, Reese and Ryan met in 1997 at her 21st birthday party. After that it went quite quickly for the Cruel Intentions stars: they got engaged in 1998 and married in 1999.

The couple has two beautiful children together who look like the spitting image of both of them, but after eight years of marriage, these lovebirds got divorced in 2007. As for us—after looking at these nine couples so far, we're questioning whether true love exists at all.

11 Hugh Grant And Liz Hurley

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Number ten on our list are Hugh Grant And Liz Hurley—two stars who ruled the '90s. They met on the set of Remando Al Viento in 1987 and pretty much immediately started dating. In 2000, after thirteen years together, the two decided to go their separate ways.

By now we're pretty sure that true love—the way they show it in the movies—does not exist. At least Hugh and Liz managed to stay close friends after their separation, and Hugh is even the godfather to Liz's son Damian. Who knows, maybe one day they'll co-star in another film and rekindle those flames!

10 Jenna Dewan And Channing Tatum


Anyone who was a young adult in the 2000s remembers how big the Step Up franchise was—especially the first installment with Jenna Dewan and Channing Tatum. Once the two met on set, they slowly started falling in love, and by 2008 the couple was engaged. They married the next year and in 2013 their daughter Everly was born.

Unfortunately, in 2018 the two stars announced that they were splitting and Jenna filed for divorce. Anyone who saw their chemistry in Step Up kind of hoped that this couple would make it to a happily ever after, but once again, the odds were not in their favor.

9 Emma Stone And Andrew Garfield

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Another Hollywood couple that everyone loved was Emma Stone and Andrew Garfield. The two met at the set of The Amazing Spider-Man in 2010 and have been dating on-and-off for a couple of years. Both refused to talk about their relationship publicly, and while they tried to keep it as private as possible, it was still well-documented by the media.

Personally, we think they were adorable together and it's a bummer they couldn't work things out. It's definitely obvious that having a relationship under the eye of the public cannot be easy—and it surely doesn't help these high-profile relationships to survive.

8 Fergie And Josh Duhamel

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Fergie and Josh Duhamel are another one of those couples who lasted for so long we were convinced they were in it for life. The two started dating in 2004, became engaged in 2007, married in 2009, and had their son Axl Jack the same year. It seemed as if they have done everything right, and in all the photos we'd see of them they always looked picture perfect and happy.

But in 2017 the two announced that they were separating—and once again that fairytale love story we all like to believe in was completely crushed. But hey, maybe some great music will come out of the split?

7 Anna Faris And Chris Pratt

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While we're talking about couples who were together for a decade, we have to mention Anna Faris and Chris Pratt. Honestly, out of all the couples on our list, this one may be one of our favorites—just 'cause the two were always goofing around and having fun. But yeah, they are on the list, which means they're not goofing around anymore.

The two met in 2007, got engaged in 2008, and married in 2009 in a small ceremony in Bali, Indonesia. In 2012 they welcomed their son and we all thought this would be one happy family forever. But in 2017 they announced their separation, and once again our hearts were ripped out.

6 Sophia Bush And Chad Michael Murray

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Here's a couple whose separation was a bit messy compared to the rest on our list. According to Biography, Sophia Bush and Chad Michael Murray got engaged in 2004 after meeting on the set of One Tree Hill and married in 2005—the same year they announced their separation.

Here's where it gets interesting: Sophia actually filed papers for an annulment, citing fraud—which she was not granted. The two officially got divorced in 2006, but still had to frequently work together on One Tree Hill. We are clearly huge Lucas and Brooke fans, which is why they made the list, but we have to admit it's a crazy story!

5 Lisa Bonet And Lenny Kravitz

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One of the coolest couples on our list (besides Winona and Johnny) is definitely Lisa Bonet and Lenny Kravitz! The two got married on Lisa's 20th birthday in 1987, and the following year she gave birth to their daughter Zoë. Unfortunately, the two separated in 1993 but managed to remain close friends.

Nowadays, Lisa is married to actor Jason Momoa, and even though we love the two together, we can't help but feel a bit sad that Lisa and Lenny are not a thing anymore... Just look at those photos of them—they were always so effortlessly unique and cool together.

4 Rachel Bilson And Adam Brody

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Next on our list is a couple that true The O.C. fans will never get over, the one and only Summer and Seth. Once it became public that Rachel Bilson and Adam Brody, who were playing the two, were actually dating in real life, the world felt like a peaceful place full of love and happiness.

Okay, we may be overexaggerating, but you get the point. After three years of dating, though, the couple split, and Rachel moved on to actor Hayden Christensen, while Adam got married to actress Leighton Meester. At least Adam and Leighton are still together, though they tend to fly under the radar these days.

3 Demi Moore And Bruce Willis

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Before we wrap things up, we had to include another great '90s couple, and this time we're talking about Demi Moore and Bruce Willis. The two got married in 1987 and have three daughters together: Rumer—born in 1988, Scout—born in 1991, and Tallulah born in 1994.

After more than ten years together, the two announced their separation in 1988 and got their divorce finalized in 2000. Of course, we're still hoping that one day they'll realize separating was the biggest mistake of their lives (especially given Demi's subsequent marriage to and divorce from Ashton Kutcher), and until then we'll just keep looking at old photos of the two.

2 Kristen Stewart And Robert Pattinson

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Anyone who thought this list would not include Bella and Edward seriously underestimated our teen obsession with vampires. There's just something about actors who play love interests on screen and then end up falling in love in real life that gets us so excited. Probably because it, in a weird way, feels as if those characters they played became reality—and who doesn't love that?

These two started being seen together off-set in 2009, and eventually it was very obvious that they were dating—even though they didn't publicly talk about it until 2012—when Kristen was snapped in an awkward pic with Snow White and the Huntsman director Rupert Sanders.

1 Jessica Simpson And Nick Lachey

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Lastly, we couldn't end this list without everyone's favorite reality TV couple, Jessica Simpson and Nick Lachey. The two met in 1998 at a Christmas party, and well, the rest was pretty well-documented in the 2003 MTV reality show Newlyweds: Nick and Jessica. And who wouldn't love watching these two singers be beautiful together?

The show aired until late 2005, and in 2006 the couple announced they were getting divorced. Luckily for us, the show lives on forever, and if we can't have Jessica and Nick together in real life anymore, at least a Newlyweds marathon will give us those happy-couple nostalgia vibes once again.

Sources: Biography, IMDB, Time

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