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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.
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."
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.
Long before Yeezy entered the picture, the E! reality star dated the rapper for a brief period of time in 2006.
The That '70s Show actress dated the former child star for almost decade up until 2011.
Their 2000 split caused major tabloid controversy, with Heche going on to marry Coleman Laffoon one year later.
Young love at its finest! The then-rising stars dated from 2001-2006.
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.
Lena Dunham's ex romanced the bombshell actress during their high school days, even attending prom together!
The New York Yankees star had the A-lister cheering him on from the stands for several months in 2008.
The A-listers struck up a two-year relationship after working together on the 2007 drama Rendition.
The Iron Man star's substance abuse issues plagued much of their highly-publicized relationship, which spanned 1984-1991.
There's no question the former baseball pro has quite the dating history, which evidently includes a one-year relationship with the Hollywood actress.
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.
Quinto and Groff dated a few years before they broke up in mid-2013, but remain friendly to this day.
After meeting on set of Felicity, the actors tied the knot in 2000. Three years later, Jen and Scott separated.
Two of a kind? The "Material Girl" songstress briefly dated the former NBA star in 1994.
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."
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."
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.