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 Ventimiglia, Reese 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.
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.
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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.
Dimitrios Kambouris/WireImage
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 Alexis 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.”
Steve Granitz/WireImage
Michael Bublé & Emily Blunt
Who knew? 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.
John Shearer/WireImage for William Rast
Kim Kardashian & Nick Cannon
Long before Yeezy entered the picture, the E! reality star dated the rapper for a brief period of time in 2006.
Dimitrios Kambouris/WireImage.com
Mila Kunis & Macaulay Culkin
The That ’70s Show actress dated the former child star for almost decade up until 2011.
SGranitz/WireImage
Ellen DeGeneres & Anne Heche
Their 2000 split caused major tabloid controversy, with Heche going on to marry Coleman Laffoon one year later.
Jon Kopaloff/FilmMagic
Jessica Biel & Chris Evans
Young love at its finest! The then-rising stars dated from 2001-2006.
Barry King/Getty Images
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.
Evan Agostini/ImageDirect
Scarlett Johansson & Jack Antonoff
Lena Dunham‘s ex romanced the bombshell actress during their high school days, even attending prom together!
Matrix/Flynetpictures.com
Kate Hudson & Alex Rodriguez
The New York Yankees star had the A-lister cheering him on from the stands for several months in 2008.
CHRISTOPHE SIMON/AFP/Getty Images
Reese Witherspoon & Jake Gyllenhaal
The A-listers struck up a two-year relationship after working together on the 2007 drama Rendition.
Jeff Kravitz/FilmMagic
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.
George Pimentel/Getty Images for Creative Artists Agency
Alex Rodriguez & Cameron Diaz
There’s no question the former baseball pro has quite the dating history, which evidently includes a one-year relationship with the Hollywood actress.
Jerod Harris/Getty Images for Sundance Film Festival)
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.
Bunny, PacificCoastNews.com
Zachary Quinto & Jonathan Groff
Quinto and Groff dated a few years before they broke up in mid-2013, but remain friendly to this day.
Jon Kopaloff/Getty Images
Jennifer Garner & Scott Foley
After meeting on set of Felicity, the actors tied the knot in 2000. Three years later, Jen and Scott separated.
Photo by Andrew D. Bernstein/NBAE via Getty Images
Madonna & Dennis Rodman
Two of a kind? The “Material Girl” songstress briefly dated the former NBA star in 1994.
Jim Smeal/WireImage
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.”
Kevin Mazur/WireImage.com
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.”
Rick Diamond/Getty Images
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?
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