15 Celebrity Couples Who Broke Off Engagements And Broke Our Hearts

March 18, 2014  |  
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Whether they were perfect for each other, or just equally perfectly broken, we thought these couples could have done one another some good. We were sad when they put a ring on it…and then took the ring off.

Kanye West and Alexis Phifer

Kanye and the lovely designer Alexis broke things off just as Kanye began to shoot into stardom. We all knew that from then on Kanye would never have a healthy sized ego again.

Britney Spears and Jason Trawick

Jason was Britney’s manager and looked over her personal affairs. After the shaved head stint and other questionable decisions, we thought having a caretaker could do her some good.




Jennifer Lopez and Ben Affleck

A) These two just have some of the most symmetrical faces in Hollywood and would have made beautiful babies and B) We always thought J Lo’s sass would be good for the calm and collected Ben.

 Nick Cannon and Selita Ebanks

We are only sad in retrospect that the two broke things off because they were super cute together, but we love Nick with Mimi too.


Zoe Saldana and Keith Britton

These two just oozed elegance, and we loved the idea of an up and coming actress being grounded by someone not in the “industry.”

Katie Holmes and Chris Klein

This is another engagement that, in retrospect, we’re sad didn’t happen. Happy-go-lucky Chris Klein could have saved Katie from the hypnotic scientologist ways of Tom Cruise. And just look at the dimples on this pair: they belonged together.

Kelly Rowland and Roy Williams

We just loved the look of the big former NFL player and the petite Miss Rowland together. And the story of the football player and singer is everyone’s favorite Hollywood fantasy.


Vivica A. Fox and Omar White

A club promoter and one of the fiercest women on television just made sense together. And perhaps their split was what made Vivica downspiral into the plastic surgeon’s office. Again and again and again.

Rachel McAdams and Ryan Gosling

The stars of “The Notebook” devastated us with their real life story more than they did in their breakthrough film when they called it quits. They should have never teased us like that. It wasn’t right.


The Game and Tiffney Cambridge

These two have been together for so long now. Perhaps what devastated us the most wasn’t that the two broke off their engagement but that they stayed together after. What was that all about?

Jesse James and Kat Von D

We just don’t think there is a more beautifully wild and broken pair out there than these two. There are few men whose company will make Kat’s neck tattoo look somehow classy.

Aretha Franklin and Willie Wilderson

We just want to see the woman whose voice has soothed us through so many heartaches find love in the last years of her life! Is that so much to ask?

Lance Armstrong and Sheryl Crow

We always had the feeling that strong-minded Sheryl kept Lance in line. And look what happened after they split? Drug scandal everywhere.

Erica Dixon and Lil’ Scrappy

The drama between these two on “Love and Hip Hop Atlanta” was almost too much for us to handle: first she said yes, then she said no. We were hoping one couple would come out normal from this show.


Julia Roberts and Kiefer Sutherland

These two starred in some of our favorite films of the 80’s and 90’s and we felt like, maybe if they’d stayed together, just maybe time could have stood still and we could have all had feathered bangs forever.

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