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 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


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?

  • Jae

    I’m totally with you on two things: I can’t accept that Ryan Gosling has had a child with Eva Mendes; and I, too, feel bad about Khloé and Lamar’s break-up.

  • I will never get over Brad and Jenn’s break up.. it is just too sad. Could you imagine how perfect those babies would have been? I can’t even think about it.

  • Autumn

    KHLOE AND LAMAR. MY FAVORITE. I honestly have so much respect for how she shows love and just…. ugh, please can they get back together?

  • Khloe and Lamar break up still has me in tears. I think they were really meant to be together, and every time I hear Khloe talking about Lamar in an episode it makes me so sad for her.

  • Oh my gosh Heidi and Seal. They’re probably the only people on this list who I legitimately thought would be together forever. I was so sad when they broke up! I’m also way too invested in celeb couples. Ha!

  • ahh this post made me sad. Rachel and Ryan forever!

  • Khloe and Lamar hurt my heart! She’s the one Kardashian I can deal with.

  • The next episode I’m watching of Friends is the one where Brad Pitt visits for Thanksgiving dinner. It always makes me sad that they split up 🙁

  • Some of these I didn’t even know were together. I’m shamefully bad at pop culture. But I will say, Orlando Bloom and Miranda Kerr were my favorite together. They’re a match in beauty heaven.

  • team aniston FOREVER! i am also really broken up over amy and will (i pretend we are friends so it feels like i have a right to feel so sad)!

  • Brad & Jen have always been the couple-I-most-want-back-together, but I love her with Justin now (how hot is he?!). I’m with you on Nina & Ian – I always think that onscreen chemistry must be real. But maybe we are onto something. I mean, how many couples start dating after filming a movie together!

  • Oh my. #15 is #1 on my list. I was just watching the Friends episode where he plays a character from Ross, Rachel, and Monica’s high school that hates Rachel. They were it! Ya know it’s pretty obvious he’s happy with Angelina what’s her face, which stinks. I blame her for all of it. Also Amy and Will should have been together forever. I still cannot believe that one.


    Also- Nina and Ian kill me. UGH.

  • Omg yes to all of these. Fellow celebrity gossip junkie over here! I read religiously, and in high school, one of my best friends used to get so mad because I could name every obscure celebrity’s child’s name but forgot his dog’s name (it was ONE TIME), ha! I was totally heartbroken over all of these, and in my mind, Rachel and Ryan will reunite one day!!

  • I still feel like Ryan Gosling and Rachel McAdams were meant to be together. Did you know they were born in the same hospital? If that doesn’t make them meant to be together I don’t know what does!

  • I volunteer to be the nice girl Jake needs.

  • One that made me sad was Zac Efron and Vanessa Hudgens. They were ADORABLE!

  • Orlando Bloom and Miranda Kerr’s child hit the good-looking gene pool jackpot. I’m sad they didn’t workout, I was rooting for them. Also, I just realized Miranda Kerr is 31. I thought she was about 24!

  • OK, maybe I’m showing my age here, but Tom and Nicole — they were together forever (n Hollywood years).

    Remember, this was when he was hot. Before everyone knew he was crazy.

  • Khloe & Lamar, Taye & Idina and Kristen & Robert bummed me out the most. I just loved reading about their relationships because they seemed so real. It’s like I could feel the love (albeit kinda weird love concern Kristen and Robert).
    I also didn’t know Heidi and Seal broke up, and now I’m kinda heartbroken for them. I loved them!

  • I’m still a little sad about Britney and Justin. Head-to-toe denim 4eva!

  • ALLL of the above! Especially Rachel and Ryan and I mean Jennifer and Brad?! Angie and Brad are just not as awesome.. I get way too sad about these celeb breakups, too!

  • #1 ughhh I loved them together!

  • Reese and Jake made me SO happy!

  • There will never be a celebrity reak up that hurts as much as Jen and Brad. You had some huge ones on here but one that I was definitely sad over was Courtney and David Arquette. But Jen and Brad // Ian and Nina are the absolute worst 🙁

  • Jen and Brad breaking up is the saddest celebrity couple break up for me. Following that is Miranda and Orlando’s break-up. I also cannot get over the fact that Ryan now has a child with Eva M.

  • Britney and Justin. Disney pop star love. It should have worked out!!!

  • Oh yeah, I briefly lost faith in relationships when Amy Poehler and Will Arnett split up. And Kim Gordon and Thurson Moore from Sonic Youth.

  • I am, and probably always will be, a Brad fan so to say I was upset by the Jen/Brad split wouldn’t quite accurately describe it haha. But I do remember exactly what I was doing when I first saw it on the news.

  • I loved Nina and Ian together. I also loved Rachel and Ryan together. Angie Harmon and Jason Sehorn recently split. This made me so sad because I was watching the night he proposed to her on Leno. Aw!

  • I know we just met. And I know that there’s a chance that you will judge me for the rest of existence based on this comment. And I feel the need to caveat it with I don’t watch all that much big people television, I somehow got stuck in a Disney loop. ALL of that said. I’m really kind of sad about Selena Gomez & Justin Bieber. I just liked the ridiculousness of the whole thing. And watching their Call Me Maybe You Tube video too many times kind of did me in as well. Anway. If you don’t show up at the #PHLBloggers event next month I will assume it was because of this comment. Apologies.

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