Home / Breakups That Broke Us

No Couple Meant More to Zillennial Theater Kids Than Zac Efron and Vanessa Hudgens

The couple originated with the "High School Musical" franchise and ended shortly after the series, but I still think about their...

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Usher and Chilli Taught Me a Crucial Lesson About Standards

'Confessions' singer Usher and TLC's Chilli broke up in 2003. Almost 20 years later, the fallout still affects how I date.

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Sometimes I Miss J-Rod

Jennifer Lopez and Alex Rodriguez dated for four years before splitting in early 2021.

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Aubrey Plaza and Michael Cera's Romance Gave Brief Hope to Weirdos Everywhere

Aubrey Plaza and Michael Cera dated quietly after meeting on the set of 'Scott Pilgrim vs. the World', though we didn't find out until...

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Camila Cabello and Shawn Mendes Were My Favorite Publicly Freaky Pair

Camila Cabello and Shawn Mendes were so unabashedly cringe-y I couldn't help but stan. And then they broke up.

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Demi Moore and Ashton Kutcher Had the Relationship I Wanted for My Divorced Mom

Ashton Kutcher and Demi Moore were together for almost a decade — and their relationship made me believe my divorced mom, like Demi, could find...

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The Only Bennifer I Have Room for In My Heart: Ben Affleck and Jennifer Garner

Ben Affleck and Jennifer Garner seemed like the perfect power couple.

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Gwyneth Paltrow and Brad Pitt Were Too Hot to Fail

Gwyneth Paltrow and Brad Pitt dated and became engaged during the '90s, and everyone — including me — thought they were perfection...

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Pete Davidson and Ariana Grande's Relationship Validated the Intense Way I Love

Ariana Grande and Pete Davidson were first linked in 2018, got engaged shortly after, and then ended the relationship less than a year later.

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Kourtney Kardashian and Scott Disick Taught Me to Trust My Eyes — Not My Heart

After over a decade together, Kourtney Kardashian and Scott Disick finally broke up. The split felt inevitable to most people, but impossible to me.

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I Stayed Single in the Hopes of Finding the Lamar Odom to My Khloé Kardashian

Khloé and Lamar had a whirlwind, playful romance — and I wanted what they had. But after four years together, they broke up, only to be reunited...

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No Couple Meant More to Zillennial Theater Kids Than Zac Efron and Vanessa Hudgens

The couple originated with the "High School Musical" franchise and ended shortly after the series, but I still think about their...

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Say What You Will About Lena Dunham, She and Jack Antonoff Have One of the Saddest Love Stories of All Time

Lena Dunham and Jack Antonoff broke up in 2018 after 5 years together. But the fallout is what stopped me in my tracks.

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Miley Cyrus and Liam Hemsworth Were Supposed to Make It, Dammit

Miley Cyrus and Liam Hemsworth were together on and off for nearly 10 years. If anyone was supposed to make it, I was sure it was 'The Last...

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Michelle Williams and Phil Elverum Had the Most Romantic Love Story of All Time

Michelle Williams and musician Phil Elverum broke up after less than a year together, shattering the illusion of moody, romantic relationships.

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Angelina Jolie and Brad Pitt's Divorce Haunted My Own Relationship

Brad Pitt and Angelina Jolie's very public, very messy, divorce made me believe I'd always be the other woman.

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I'll Never Forget When Katy Perry Was Dumped by Russell Brand via Text Message

Katy Perry's divorce from Russell Brand was famously featured in her tour documentary, 'Part of Me,' and as a post-grad I deeply...

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I Thought Paris Hilton and Paris Latsis Had a Chance — Even After She Complained About the $4.7 M Ring

Paris Hilton's 2005 engagement to Greek shipping heir Paris Latsis was a match made in tabloid heaven. Until it wasn't.

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Freida Pinto and Dev Patel's "Amicable" Split Was My Parents' Divorce All Over Again

Freida Pinto and Dev Patel dated for six years after meeting on the set of 'Slumdog Millionaire.' Their "amicable" breakup still...

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Jennifer Garner and Michael Vartan Were the Only Couple I Shipped — Until I Learned About Fuckbois

'Alias' stars Jennifer Garner and Michael Vartan's breakup was personally challenging for one writer.

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Rihanna’s Breakup With Her Billionaire Boyfriend Killed My Power Couple Fantasy

Rihanna and Hassan Jameel, a billionaire businessman, made me wonder if I could actually live out my power couple dreams. The singer and the Jameel...

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Janelle Monáe and Tessa Thompson Were the Best Couple That Never Was

Janelle Monae and Tessa Thompson may have been the hardest-to-handle on-again-off-again relationship that never was quite official. Especially for...

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Prince Harry and Chelsy Davy's Breakup Showed Me Love Doesn’t Always Conquer All

Prince Harry dated Chelsy Davy on and off from 2004 to 2010. It seemed like their love was true, but Davy knew she didn't want a life in the...

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Kirsten Dunst and Jake Gyllenhaal's Breakup Is Forever Linked to My Parents' Divorce

Kirsten Dunst and Jake Gyllenhaal are forever linked to the ideal of young love between indie darlings, an iconic salad photo, and my parents'...

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Angelina Jolie and Billy Bob Thornton Were an Absolutely Chaotic Couple and I Loved Them for It

When Angelina Jolie and Billy Bob Thornton wed in 2000, and when their marriage ended two years later, it felt like the end of the wild, insatiable...

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Helena Bonham Carter and Tim Burton’s Split Killed My Dream of Never Cohabiting with My Partner

When Helena Bonham Carter and Tim Burton broke up, it killed my dreams of living separately from a partner.

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I Will Never Understand Chris Evans and Jenny Slate's Perfect Relationship

Jenny Slate and Chris Evans were two halves of the perfect couple - even if I didn't understand the dynamic of their relationship.

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When the Spice Girls Broke Up, I Realized Friendship Does Actually End

The universe's supply of girl power decreased 20% the day Geri Halliwell left the Spice Girls. What is a world without Ginger Spice? Here's...

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