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The Saddest Celebrity Breakups Of All Time

There’s nothing quite like getting far too invested in a celebrity relationship, am I right? The unadulterated joy you get from projecting your fantasies onto total and complete strangers. The inexplicable rush upon seeing photos of them on a red carpet, looking better than you probably will in your whole life. The perverse satisfaction derived from “insider news” from “trusted sources” that definitely wasn’t planted by either of their publicists. It’s one of the simple, incredibly invasive pleasures of living in the 21st century.

But as the saying goes: celebrities, they’re just like us! Which means their relationships fail, even though we swore this time they wouldn’t. Except what’s different here is that the entire world watches and interjects their unwarranted opinions into what is already a horrifying and traumatic period of two people’s lives. Remember that time, in a blissful era where he wasn’t the leader of the free world, that Donald Trump tweeted (repeatedly) about Robert Pattinson and Kristen Stewart’s breakup? Imagine that, but coming from every mother with a Facebook account across the entire world.

While many celeb breakups are expected, pre-ordained from the moment that first paparazzi photo hits TMZ, there are a handful of splits that managed to send shockwaves around the world, that seemed to rock the very foundation upon which the notion of love so perilously rests. These are their stories.

Vanessa Hudgens And Zac Efron

Listen. I know some of you don’t care about this couple at all and to that I have one thing to say: you’re wrong. Zanessa kicks off our list because, at the tender age of 14, I sat directly behind them on the Pirates of the Caribbean ride at Disneyland and nearly burst into tears afterwards, so believe me when I say my world was rocked by this breakup.

Some of you weren’t in the midst of your painful and pivotal middle school years when High School Musical dropped—meaning your mid-pubescent romantic renaissance wasn’t awoken by the young love between Troy Bolton and Gabriella Montez—and it SHOWS.

Zanessa were the embodiment of young Hollywood from approximately 2005–2010. They were simultaneously everything we wanted to be and everything we could never have. To this day I couldn’t tell you which one I was actually more jealous of, but just that I still think back on them fondly, quietly hoping that they do the same of each other.

Rachel McAdams And Ryan Gosling

Listen: God doesn’t give with two hands. You don’t get to look like Rachel McAdams or Ryan Gosling and then end up with Rachel McAdams or Ryan Gosling. You don’t get to play one of the most essential romantic couples of the 21st century and then live happily ever after together, okay?? That notion, while comforting for the rest of us, doesn’t make this breakup any less sad.

What did, however, make it almost unbearable was knowing that this kind of passion existed in the world and now no longer does. As if we needed one more reminder that nothing good can last forever.

That video looks like it was filmed on a flip phone in the pre-historic era, and that’s because it probably was, but it doesn’t even matter! No amount of terrible camera quality can dampen the raw passion of this scene. Please indulge me for a moment as we all take a stroll down memory lane to the 2005 VMAs.

The award was “Best Kiss” and the competition was nonexistent. The era was peak The Notebook fever, a time when we all actually waxed poetic about Alzheimer’s. This sequence, so choreographed, so perfect, so effortless in its ability to remind us that we are mere mortals existing at the leisure of an indifferent God, will live in infamy.

The “come hither” finger gesture? The effortless lift? The goofy smile on her face afterwards? The casual way Ryan Gosling strolls to the podium with Rachel McAdams resting on his hip like a basket of freshly washed laundry? Unparalleled, all of it. I don’t care if the rest of their relationship was utter garbage; it was all worth it for this sacred moment in pop culture history.

Will Arnett And Amy Poehler

You know how every time any notable celebrity couple breaks up and every single person in the universe takes to Twitter to say the exact same thing: love is dead!!!! Amy and Will were that first couple for me.

These two were a beacon of hope in my early-adolescence, a North star by which I could guide my own life. You see, Will and Amy instilled in me the (wildly naïve) belief that one day, I too could marry a man just as funny as I, and then we could live the rest of our lives together being funnier than everyone else. What can I say? I was young. I was innocent. I was still under the incredibly mistaken impression that Will Arnett was as funny as Amy Poehler.

Regardless, the end of Will and Amy was the end of an era, one in which we all breathed a little lighter and dreamed a little higher. At least we have their adorable, inexplicably red-haired children to remember them by.

Jennifer Aniston And Brad Pitt

This breakup wasn’t sad so much for the end of the relationship itself, but more so because of what it created. The end of Jennifer Aniston and Brad Pitt kicked off a decade long, unnecessarily cruel Spinster Hunt, targeted at a woman who deserved not one bit of it, instead of the man who cheated on her. Weird, right? Almost like double standards exist or something.

You want to talk about life being unfair? Let’s talk about Jennifer Aniston. I mean, sure, she gets to look like Jennifer Aniston. But I think she earned those arms and the rest of that age-proof body after going through what she did.

First, her husband cheats on her with Angelina Jolie, another woman so inhumanely beautiful that it breaks my brain to imagine them existing on the same plane of existence. Then the two suffer a public, nasty divorce, during which constant media coverage compares and contrasts two women who have no business being pitted against one another.

From then on out, no matter the circumstance, Jennifer will be harassed throughout every relationship she pursues. If she’s happy and thriving, it’s a countdown to the inevitable doom. If it ends, for any reason whatsoever, headlines everywhere read “Will Jennifer Ever Find Love Again?” or “Jennifer Alone Forever.”  The woman can’t win.

And now, nearly 14 years later, the rumors have started up again! Will they? Won’t they? What does Angelina think? What kind of woman takes back a cheating husband? How much more money can we squeeze out of this tired story?

Leave Jennifer alone! Let her live! Let her f*ck her stupid hot ex if she wants to! Thank you for coming to my Ted Talk!

John Krasinski And Emily Blunt 

JUST KIDDING! But please take this as my formal notice that, in the event of this ever happening, I will be shipping myself to the convent that Katy Perry keeps trying to steal from those nuns.

Images: Giphy (5)

Mary Kate Fotch
Mary Kate recently moved to Amsterdam, where she spends a good chunk of her time trying to not die on a bike. She was forced to develop a sense of humor at an early age for many reasons, not the least of which being that she grew up with the name Mary Kate during the Olsen twin era. Follow her on Instagram if you're interested almost exclusively in Huji edits or stories about her overweight cat.