16 Celebrity Exes Who Awkwardly Crossed Paths at the 2025 Golden Globes

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January 6, 2025 at 3:04pm EST

The 2025 Golden Globes was a who’s who of Hollywood’s most famous faces so, inevitably, some of these stars have history!

While there were definitely plenty of adorable moments from Hollywood’s cutest couples on the red carpet and fashionable moments from best-dressed stars, there were a couple of potentially awkward run-ins from celebrity exes.

We’ve all been there, you show up to a party and your ex is there. Well, count yourself lucky that there were no cameras around unlike at the Golden Globes.

For stars like Leighton Meester, Sebastian Stan and Angelina Jolie, the red carpet was filled with past loves and scorned exes, and we do not envy these stars for having to navigate (and avoid) a run-in.

See which celebrity exes shared the red carpet at the 2025 Golden Globes.

Billy Bob Thornton & Angelina Jolie

Image Credit: Jason Armond / Los Angeles Times via Getty Images, Michael Buckner/GG2025

After freshly finalizing her divorce from ex-husband Brad Pitt, Angelina Jolie was on a high at the 2025 Golden Globes — even though two other exes were in attendance!

Jolie’s ex-husband Billy Bob Thornton was in attendance with his wife of 10 years Connie Angland. Jolie and Thornton married in 2000 after two months of dating and separated in 2002.
Angelina Jolie & Colin Farrell

Image Credit: JC Olivera/GG2025

Angelina Jolie and Colin Farrell were briefly linked after filming 2004’s Alexander together — in which Jolie, oddly enough, played Farrell’s mother. However, their romance never quite got off the ground.

Farrell, who won an award in the Best Actor in a Limited Series category for his work in The Penguin, attended the event solo while Jolie took her daughter as her plus one. Does that mean they’re both single?
Timothée Chalamet & Eiza González

Image Credit: Earl Gibson III/GG2025, Michael Buckner/GG2025

Timothée Chalamet only had eyes (and hands) for girlfriend Kylie Jenner at the 2025 Golden Globes, where he was nominated for his role in A Complete Unknown.

However, the couple did share the room with actress Eiza González who Chalamet had a brief summer fling with back in 2020.
Kieran Culkin & Emma Stone

Image Credit: John Nacion/GG2025, John Nacion//GG2025

The most wholesome ex crossover of the night belonged to Kieran Culkin and Emma Stone who were attending thanks to their project, A Real Pain. Stone, alongside her husband Dave McCary, produced the film in which Culkin stars. Culkin also won for his supporting role!

Stone and Culkin dated from 2010 to 2011 after meeting on the set of the 2009 movie Paper Man but have been close friends ever since.
Sebastian Stan & Leighton Meester

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Gossip Girl fans, this might be the closest we’re getting to a reunion! Sebastian Stan and Leighton Meester, who you might know better as Carter Baizen and Blair Waldorf, dated 2008 until 2010 after meeting on the show.

However, both attended the 2025 Golden Globes with their now-partners. Meester was there to support husband Adam Brody who was nominated for his role in Nobody Wants This. Stan attended with girlfriend Annabelle Wallis and won a Golden Globe for his leading role in A Different Man.
Edward Norton & Salma Hayek

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Another of Hollywood’s forgotten couples crossed paths at the Golden Globes! Salma Hayek and Edward Norton met in 1999 and dated until their breakup in 2003.

Norton attended with his wife Shauna Robertson while Hayek, who is married to François-Henri Pinault, flew solo.
Emma Stone & Andrew Garfield

Image Credit: JC Olivera/GG2025, Gilbert Flores/GG2025

In addition to celebrating with ex-boyfriend Kieran Culkin, Emma Stone also shared the room with Andrew Garfield who she famously dated for four years before their 2015 split after they met on the set of The Amazing Spider-Man in 2011.
Jake Gyllenhaal & Kirsten Dunst

Image Credit: Earl Gibson III/GG2025, Gilbert Flores/GG2025

Who could forget this 2000s power couple? Jake Gyllenhaal and Kirsten Dunst dated from 2002 until 2004 but have long since separated.

Dunst attended with husband of two years Jesse Plemons, who was nominated for his role in Kinds of Kindness.