Zac Efron and Vanessa Hudgens
I can’t help this one. Every time I think of these two the song “The Start of Something New” starts playing and I get the urge to dance and cry. While Vanessa’s current relationship with Austin Butler is also cute as hell (have you seen their Coachella photos?) a part of me still wishes the most iconic couple of my childhood had stayed together.
Angelina Jolie and Brad Pitt
Why couldn’t this relationship work out? Why! From the moment I watched Mr. & Mrs. Smith I wanted these two to be a couple — sorry Jen. Their chemistry was undeniable and after having three biological and adopted children together I truly thought they’d beat the Hollywood odds and stay together.
Ben Affleck and Jennifer Garner
These two still hang out on occasion, but that doesn’t make the sting of this break up any less painful. At least now I have another reason to cringe while watching Daredevil.
Courteney Cox and David Arquette
After starring in several of the Scream movies together it came as a total shock when this couple decided to call it quits in 2013. I guess that Friends gag where they added “Arquette” to the entire cast’s name needs to be amended, huh?
Alexa Chung and Alex Turner
Every hipster both cried and cheered when this stylish couple broke up. Alex’s band, Arctic Monkeys, released one of their most popular albums to date post-break up and I can’t help but think the songs are about Alexa.
Ryan Gosling and Rachel McAdams
Even though there are numerous reports of these two hating each other while on the set of The Notebook they soon became an item — I bet it was that kissing in the rain scene that did it. Ryan is now a happy husband to Eva Mendes, but it still would’ve been nice to see these two grow old together.
Winona Ryder and Johnny Depp
Is there a single fan of the grunge-era who didn’t cry about the end of this relationship? These two were the perfect couple both on and off camera — remember Edward Scissorhands? I guess the relationship just wasn’t meant to last “forever“.
Reese Witherspoon and Ryan Phillippe
The pair met on Reese’s 21st birthday, married a year later and had two kids but unfortunately it just wasn’t meant to last. They broke up a decade ago and every time I watch Cruel Intentions I want to cry.