The 15 Most Sob-Worthy Celebrity Breakups

Hi, my name is Nadine and I’m a secret celebrity gossip junkie. Hi, Nadine.

I distinctly remember finding a copy of the People Magazine issue with the beautiful Princess Diana on the cover in my parents house, soon after my Dad married my Step-mom. I remember exactly where I was as I flipped through it, confused why anyone would care about people they didn’t know. Who are these people? Why are they famous? And why does my (then new) Step-mother even care?

Fast forward to today. I visit Us Magazine and People.com more than I’d like to admit. I could tell you what any celebrity named their baby. Seriously. Try me. Gwen Stefani and Gavin Rossdale? Kingston, Zuma, and Apollo. Naomi Watts & Liev Schreiber? Samuel and Alexander (known as Sasha). Yeah, I know nicknames too. And let’s not forget, I predicted North West’s name and came decently close for Prince George.

So as you can imagine, sometimes a certain celebrity couple doing some “conscious uncoupling” really bums me out. Though Gwyneth and Chris didn’t. Here’s some who did.

1. Ashley Simpson and Pete Wentz

ashlee simpson and pete wentz

Maybe because she’s got edge or maybe because she put out one of my favorite albums of the 00’s (Autobiography, duh), but Ashlee has always been my favorite Simpson. And I just really wanted them to work!

2. Reese Witherspoon and Jake Gylenhall

Reese Witherspoon and Jake Gyllenhaal

They seemed so down to earth! He was good with her kids! They did family stuff!

3. Jake Gylenhall and Taylor Swift

Jake and Taylor

They were a thing for a total of what? Two seconds? Okay okay! I just want Jake to settle down with a nice girl.

4. Nina Dobrev and Ian Somerholder

nina and ian

I have no idea why this bummed me out so much, except that I feel like they had amazing chemistry on The Vampire Diaries and I always pretend that translates to real life.

5. Robert Pattinson and Kristen Stewart

Kristen Stewart and Robert Pattinson

Some of you might hate me for having this one on the list but hey, these two sure kept things interesting.

6. Susan Sarandon and Tim Robbins

Susan Sarandon and Tim Robbins

20 years in together in Hollywood? Well done.

7. Rachel McAdams and Ryan Gosling

Ryan Gosling and Rachel McAdams

If you’re a bird, I’m a bird. IT FELT SO REAL. And now he had to go and have a kid with Eva Mendes. Mehhhhhh.

8. Michelle Williams and Jason Segel

Michelle Williams and Jason Segel

When I found out they were together I remember thinking “Yeah, I get that. They make sense.” I hoped his humor would heal her heart. He seemed like he was good with her kid. They did normal family stuff in Brooklyn. Sob.

9. Amy Pohler and Will Arnett

Amy Poehler and Will Arnett

Honestly, I really just feel like family dinners in their household would have been amazing.

10. Heidi Klum and Seal

heidi-and-seal

They could have at least procreated 5 more times before splitting. The world needs more people as beautiful as their kids.

11. Taye Diggs and Idina Menzel

idina menzel and taye diggs
A match made in broadway heaven!

12. J.Lo and Puffy

J Lo and P Diddy

I KNOW. Seriously, Nadine? J.Lo and Puffy? BUT YES. Everyone knows she was so much better with him that with Marc Anthony (ick). She’s Jenny from the Block! She needed a bad boy like Puffy.

13. Orlando Bloom and Miranda Kerr

Miranda and Orlando

They seemed chill. Bummer.

14. Khloe Kardashian and Lamar Odom

lamar odom and khloe kardashian

Everything about their breakup made me sad. Even now when Khloe references Lamar in recent episodes of K&K take the Hampton’s, I’m sad all over again. Kudos to Khloe for handling everything (and we know it was a lot), like a respectful, kind, and loving person. Every once in a while an article pops up that they are reconciling and I get my hopes up.

15. Brad Pitt and Jennifer Aniston

Jennifer Aniston and Brad Pitt

You knew this had to be on the list, didn’t you? I remember exactly where I was when I found out they were splitting. It was the cover of a tabloid magazine in my orthodontist office and my 16-year-old self just could not handle all the feelings.

Which celeb breakup bummed you out the most? Do you have one to add to this list?

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