20 Celebrity Exes You Probably Forgot Existed

From Ryan Reynolds and Alanis Morissette's short-lived engagement to Kate Hudson's fling with Alex Rodriguez, take a trip down memory lane with these celeb exes.

By McKenna Aiello May 02, 2020 12:00 PMTags
Watch: Top 5 Most Expensive Celebrity Divorces

Pat Benatar said it best—love is a battlefield. 

Finding your happily ever after isn't impossible in Hollywood, but it's no secret that some celebs have kissed quite a few frogs before finding their prince or princess.

In the early days of their careers, stars like Alexis Bledel and Milo VentimigliaReese Witherspoon and Jake Gyllenhaal found love on set, while others (we're looking at you Scarlett Johansson and Jack Antonoff) dated long before they ever got their big break. 

Without further ado, it's time to look back at 20 couples that despite not going the distance, still hold a special place in our hearts.

Celebrity Exes You Probably Forgot Existed

From Ryan Reynolds and Alanis Morissette's short-lived engagement to Kate Hudson's fling with Alex Rodriguez, take a trip down memory lane with these celeb exes.

Matthew Perry & Julia Roberts

In his memoir Friends, Lovers and the Big Terrible Thing, Perry opened up about his two-month '90s romance with the Oscar winner, which began after Roberts agreed to guest star on Friends under one condition.

Perry wrote that the Pretty Woman actress "would only do the show if she could be in my story line," adding that he "had to woo her." To do so, he sent Roberts three dozen roses and a note that read, "The only thing more exciting than the prospect of you doing the show is that I finally have an excuse to send you flowers."

But their romance was ultimately shortlived because "dating Julia Roberts had been too much for me," Perry admitted. "I had been constantly certain that she was going to break up with me. Why would she not? I was not enough; I could never be enough; I was broken, bent, unlovable. So instead of facing the inevitable agony of losing her, I broke up with the beautiful and brilliant Julia Roberts."

Alanis Morissette & Ryan Reynolds

We have Drew Barrymore's 2002 birthday bash to thank for this unlikely celeb pairing. The Canadian stars even got engaged two years later, but called it quits in early 2007.

Milo Ventimiglia & Alexis Bledel

During their Gilmore Girls days, the co-stars struck up an offscreen romance between 2002-2006. The pair even discussed marriage at one point, with Bledel telling People, "I think everybody who has been dating for more than a couple of years probably talks about it at some point. It's a fun thing for us to talk about, but that's it."

Michael Bublé & Emily Blunt

The Devil Wears Prada alum dated the pop singer for three years up until 2008. Seven years later, Bublé denied rumors that a cheating scandal was to blame for their split. 

Kim Kardashian & Nick Cannon

The E! reality star dated the rapper for a brief period of time in 2006. 

Mila Kunis & Macaulay Culkin

The That '70s Show actress dated the former child star for almost a decade up until 2011. 

Ellen DeGeneres & Anne Heche

Their 2000 split caused major tabloid controversy, with Heche going on to marry Coleman Laffoon one year later. 

Jessica Biel & Chris Evans

Young love at its finest! The then-rising stars dated from 2001-2006. 

Christina Applegate & Brad Pitt

Rumor has it that the Dead to Me star ditched her date to the 1989 MTV Video Music Awards, who just so happened to be the one and only Mr Pitt. 

Scarlett Johansson & Jack Antonoff

The Bleachers singer romanced the Black Widow actress during their high school days, even attending prom together. 

Kate Hudson & Alex Rodriguez

The New York Yankees star had the A-lister cheering him on from the stands for several months in 2008.

Alex Rodriguez & Cameron Diaz

There's no question the former baseball pro has quite the dating history, which includes a one-year relationship with the Hollywood actress. 

Reese Witherspoon & Jake Gyllenhaal

The A-listers struck up a two-year relationship after working together on the 2007 drama Rendition

Sarah Jessica Parker & Robert Downey Jr.

The Iron Man star's substance abuse issues plagued much of their highly-publicized relationship, which spanned 1984-1991.

Common & Laura Dern

The hip-hop artist and actress sparked romance rumors after working on the 2018 thriller The Tale, but Common would later describe their relationship as strictly platonic. 

Zachary Quinto & Jonathan Groff

Quinto and Groff dated a few years before they broke up in mid-2013, but remain friendly to this day. 

Jennifer Garner & Scott Foley

After meeting on set of Felicity, the actors tied the knot in 2000. Three years later, they separated. 

Madonna & Dennis Rodman

Two of a kind? The "Material Girl" songstress briefly dated the former NBA star in 1994.

Sandra Bullock & Matthew McConaughey

These two became the subject of romance rumors after co-starring in A Time to Kill, which ultimately turned into a two-year relationship.

Asked by Cosmopolitan in 2003 how they managed to stay friends, Bullock said, "It's the work we both put in. There's a great amount of respect and love. I feel very cared for by Matthew. No matter where he is in his life or where I am in mine—he could be married—I know we would stay close."

Tom Cruise & Penelope Cruz

2001's Vanilla Sky brought the A-listers together for a three-year relationship. Cruz's rep denied that Scientology played a role in the breakup, saying that the actress, while not a Scientologist, had found the church courses she took "beneficial."

Lenny Kravitz & Nicole Kidman

The singer and actress called off their engagement in 2003, but the universe brought them back together when Kidman co-starred in Big Little Lies alongside Kravitz's daughter, Zoë Kravitz

Which unlikely love story surprised you the most?