Celebrity exes running into each other at award shows and events is an inevitable occupational hazard.
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As anyone who has ever crossed paths with a former lover at a mutual friend’s party or in a local coffee shop knows, it is one of the most awkward things a person can experience. Now imagine doing it with cameras and millions of people watching? Count us out.
For stars like Brad Pitt, who has many exes working in his industry, running into an ex happens so often that he seems to handle the awkwardness better than most. Then there are stars like Vanessa Hudgens who attempts to avoid all eye contact with her ex-boyfriend, Austin Butler, became a viral video. Or Miranda Kerr and Orlando Bloom whose red carpet run-in was caught on camera too. And don’t even get us started on the exes who ran into each other while attending an event with a new partner!
Stars really are just like us! They’ve had breakups that are messy, amicable and everything in between and they too feel the urge to jump into the nearest bush when they run into an ex. Except, in their case, there is no hiding on a red carpet or at an award show when there are cameras covering all angles.
With a hectic award show season every single year, stars can’t help but have their share of uncomfortable run-ins. To relieve their pain, we’ve compiled the times famous exes crossed paths and were caught on camera.
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Brad Pitt & Jennifer Aniston
Image Credit: Emma McIntyre/Getty Images for Turner After being part of one of Hollywood’s most dramatic divorces and affair scandals, who would have expected that Brad Pitt and Jennifer Aniston would have ever shared the same air? The exes seemed to leave the past in the past at the 2020 SAG Awards when they shared a heartfelt, yet still a little hard to watch, moment after they both took home awards.
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Brad Pitt & Gwyneth Paltrow
Image Credit: Tammie Arroyo/Getty Images Pitt is no stranger to dodging, or even supporting, exes at events. He has also shared a space with former girlfriend Gwyneth Paltrow, including at the 2020 Golden Globes where Aniston was also in attendance.
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Miranda Kerr & Orlando Bloom
Image Credit: Jon Kopaloff/FilmMagic via Getty Images In 2013, Miranda Kerr and Orlando Bloom posed lovingly together at the Vanity Fair Oscar Party but by the following year, their attendance at the event looked very different.
After announcing their separation in October 2013, the exes attended the event separately in February 2014 and cameras caught Bloom awkwardly interupting one of Kerr’s interviews to greet his former wife.
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Sofía Vergara & Nick Loeb
Image Credit: Walter McBride/Corbis via Getty Images Sofía Vergara and Nick Loeb dated from 2010 until 2014 and if their ongoing legal battle over frozen embryos is anything to go by, we’re guessing it is far from amicable between the exes.
So when cameras caught Vergara appearing to ignore Loeb after he greeted her during an interview on a 2014 red carpet, the second-hand embarrasment was real.
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Casper Smart, Jennifer Lopez & Sean Combs
Image Credit: Charley Gallay/Getty Images for Chopard Running into an ex is awkward but running into an ex while with your new boyfriend is just down right excruciating. Luckily Jennifer Lopez managed to survive introducing her boyfriend, Casper Smart, to her ex, Diddy, at the 2013 Golden Globes After Party.
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Harry Styles & Taylor Swift
Image Credit: Andrew H. Walker/WireImage via Getty Images Like Rihanna, we had our popcorn out when Taylor Swift and Harry Styles both attended the 2013 VMAs months after their breakup. While we don’t know if the two spoke at the show, photographers did catch Swift swiftly passing Styles. She was also seen allegedly muttering something rude while Styles was accepting an award with his One Direction bandmates.
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Lenny Kravitz & Nicole Kidman
Image Credit: Kevin Mazur/WireImage via Getty Images When you’re as cool, calm and collected as Lenny Kravitz, there is no such thing as an awkward moment. But we’re betting that Nicole Kidman felt at least slightly uncomfortable while posing with her former fiancé, who she dated briefly in 2003, and her now-husband, Keith Urban, at the 2013 CMT Music Awards.
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Renée Zellweger & Bradley Cooper
Image Credit: Kevin Winter/Getty Images Renée Zellweger and Bradley Cooper’s romance was never officially confirmed by the couple but, after meeting on the set of Case 39 in 2006, they were reported to be living together in 2010. By 2011, the couple called it quits.
In 2020, the pair ran into one another and were photographed chatting at the Oscars.
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Blake Shelton & Miranda Lambert
Image Credit: Heather Wines/CBS via Getty Images Country music award shows have been an uncomfortable affair for Miranda Lambert and Blake Shelton ever since their 2015 divorce but they have largely avoided one another.
However, in 2019, Shelton was sitting front and center with new partner Gwen Stefani during Lambert’s CMT Awards performance which may have included a dig at her ex-husband.
During a performance of “Little Red Wagon,” Lambert sang, “got the Hell outta Oklahoma,” which references Shelton’s home state.
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Demi Lovato & Joe Jonas
Image Credit: Kevin Mazur/VF17/WireImage via Getty Images Demi Lovato and Joe Jonas posed for photos together at the Vanity Fair Oscars Party in 2017, seven years after their breakup, while Jonas was dating future wife Sophie Turner.
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Billy Crudup & Claire Danes
Image Credit: Peter Kramer/Getty Images Billy Crudup and Claire Danes, pictured here in 2006, were both nominated for SAG Awards in 2016, ten years after their split.
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Harry Styles, Cara Delevigne & Kendall Jenner
Image Credit: David M. Benett/Getty Images Harry Styles’ December 2014 appearance at the British Fashion Awards will go down in pop culture history thanks to this photo of him running into Cara Delevigne and Kendall Jenner.
Delevigne and Styles were romantically linked in 2013. Styles and Jenner were spotted on a few dates in late 2013 and early 2014 but actually ended up striking up their on-off romance again shortly after the award show.
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Emma Stone & Kieran Culkin
Image Credit: Matt Winkelmeyer/MG22/Getty Images for The Met Museum/Vogue Emma Stone and Kieran Culkin dated between 2009 and 2011 but luckily they seem to have kept thing civil by the looks of this 2022 Met Gala appearance.
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Vanessa Hudgens & Austin Butler
Image Credit: WireImage After ending the 10-year relationship in 2019, Vanessa Hudgens and Austin Butler awkwardly skirted around each other at the 2023 Oscars where Butler was nominated for Best Actor and Hudgens was hosting the pre-show.
Butler was interviewed by Hudgens’ co-host but the two were seen in close proximity when the actress avoided eye contact while passing the Elvis star.
