By Megan Riedlinger
8:02am PST, Feb 14, 2024
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Join us as we look back at some of the celeb couples who split on or around Valentine's Day, starting with this duo…
Jennifer Aniston and Justin Theroux started dating in 2011, got engaged in 2012 and tied the knot in 2015, but it wasn't meant to be: They announced their breakup the day after Valentine's Day in 2018. "In an effort to reduce any further speculation, we have decided to announce our separation," they said in a statement. "This decision was mutual and lovingly made at the end of last year. We are two best friends who have decided to part ways as a couple, but look forward to continuing our cherished friendship."
Keep reading to see more stars who went through similarly unfortunately timed breakups…
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Does Kanye West have a Valentine's Day curse…?! The rapper spent the first month and a half of 2022 enjoying a whirlwind romance with actress-artist Julia Fox after they met in Miami on New Year's Eve. But it wasn't meant to be: On Feb. 14, 2022, her rep released a statement announcing that they were "no longer together." The "Uncut Gems" star also addressed the breakup on her Instagram Story on V-Day, writing, "Kanye and I are on good terms! I have love for him but I wasn't in love with the man."
MORE: Famous couples reveal how they met and fell in love
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Days after Lady Gaga attended the 2019 Grammy Awards on Feb. 10 without agent Christian Carino — or the engagement ring he gave her when he popped the question in 2017 — her rep confirmed to People magazine that they'd called it quits.
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In 2015, Regina King opened up to Us Weekly about the time she got dumped on V-Day: "Someone broke up with me on Valentine's [Day]," she said, adding, "Then he actually sent me flowers that said, 'I still love you,' and I threw the flowers in the trash." Fans assumed she was talking about her famous ex Malcolm-Jamal Warner — from whom she split in 2013 — though she never publicly named him.
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Milo Ventimiglia and Hayden Panettiere threw in the towel just a few days after Valentine's Day in 2009. The stars kicked off their two-year relationship while co-starring on "Heroes" when she was 18 and he was 30.
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Just one day after Valentine's Day in 2012, the news broke that "One Tree Hill" co-stars Sophia Bush and Austin Nichols had officially called it quits after six years of off-and-on coupledom.
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What's worse than a breakup before Valentine's Day? A really tumultuous breakup that makes headlines right after the holiday. When "I Am Number Four" co-stars Dianna Agron and Alex Pettyfer called it quits in February 2011 after less than a year of dating, things reportedly got so nasty, the "Glee" star moved out of the home they shared right around V-Day — mere days before their sci-fi flick debuted on Feb. 18.
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Jude Law and Sienna Miller ended their on-again, off-again love affair less than a week before Valentine's Day in 2011.
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Shortly before Valentine's Day in 2016, Nina Dobrev and Austin Stowell went their separate ways following seven months of coupledom. The actress hinted at the breakup when she took to social media on V-Day to share a photo of herself with her friends, which she captioned, "Sunday Funday #HappyGALentinesDay."
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Nick Jonas and Delta Goodrem dated for about nine months in 2011 when he was 19 and she was 27. A week after Valentine's Day in 2012, the age-mismatched singers confirmed that they'd thrown in the towel.
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Jordin Sparks and Sage the Gemini shared their breakup news just four days before Valentine's Day in 2016. They'd been an item for about nine months.
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Hilary Duff filed to divorce Mike Comrie in February 2015 — a year after they separated in early 2014. The divorce was finalized in February 2016 — about a week and a half before Valentine's Day.
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Bam Margera's second wife, Nicole "Nikki" Boyd, filed for legal separation from the former "Jacka**" star on Feb. 15, 2023 — just one day after Valentine's Day. (Court papers listed their actual breakup date as Sept. 14, 2021.) Her attorney told People magazine that Nikki felt she had no choice but to finally file "due to [Bam's] continuing drug and alcohol abuse, erratic behavior, and due to his failure to provide support for her and their son," adding, "Nikki has put everything she has into trying to get Bam to stay sober, and to trying to preserve her family."
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Actor Tim Robbins filed to divorce Gratiela Brancusi on Jan. 27, 2021 — just a couple weeks before Valentine's Day. It came as a huge surprise because no one knew the couple of about three years had even tied the knot.
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On Feb. 3, 2021 — just 11 days shy of Valentine's Day — Us Weekly reported that actress Patricia Rahman filed to divorce "Buffy the Vampire Slayer" actor James Marsters following their 10th wedding anniversary the previous month.
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Rebel Wilson and Jacob Busch called it quits in early 2021 — just a few months after they made their relationship Instagram official in September 2020. The Australian actress revealed her single status on Instagram on Feb. 2, 2021, captioning a photo of herself, "Lots on my mind… aghhhhhh… #single-girl-heading-to-Super-Bowl!" Two days later, Us Weekly reported that Rebel dumped the Anheuser-Busch scion via text in mid-January.
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Simon Baker and his wife of 29 years, Rebecca Rigg, called it quits shortly before Valentine's Day on Jan. 29, 2021. "We remain close friends and our three children will always be the most important focus of our lives," they said in a statement shared with People magazine, which reported they'd actually quietly separated the previous April.
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Amanda Seyfried and Ryan Phillippe briefly dated from late 2010 to early February 2011. They reconnected that March but called it quits for good just four months later.
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"Teen Mom" star Maci Bookout split from Kyle King a week before Valentine's Day in 2012 after she caught him cheating on her. Though they briefly reconciled, it ultimately wasn't meant to be for the couple of about two years.
