Being a member of the Hollywood elite doesn’t protect you from romantic disasters. These 15 celebs had relationships that fell apart on or around the year’s most romantic day. *face-palm*
Kelly Osbourne & Bert McCracken
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Kelly dated the grunge rocker in 2002, during the second season of the TV show, The Osbournes, which caused some tension as he was not well-liked among the rest of the family.
Kelly Osbourne & Bert McCracken
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Instincts were correct when Bert dumped Kelly on Valentine’s Day. Nice!
Justin Theroux & Jennifer Aniston
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Everything seemed rosy for the pair, who married in 2015 after dating for four years.
Justin Theroux & Jennifer Aniston
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Unfortunately, it wasn’t to be, as the couple both announced their separation two years later. However, the two are still good pals and regularly pop up in pics on each other’s social media.
J-Lo & P Diddy
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The pair’s highly-publicized relationship came to a blinding halt around Valentine’s Day in 2003 after rumors began to swirl that Diddy was doing the dirty behind J-Lo’s back.
J-Lo & P Diddy
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Jennifer told the press that while she never caught him red-handed, “she just knew.”
Kim Kardashian & Kayne West
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These two are always close to tabloids for one reason or another. However, the duo shocked the world when they announced their marriage had ended in 2021.
Kim Kardashian & Kayne West
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The pair cited “irreconcilable differences” as their reason for calling it a day.
Julia Fox & Kanye West
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West appears again! The two dated for a month at the beginning of 2022 before calling it quits circa Valentine’s Day.
Julia Fox & Kanye West
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Supposedly Julia grew quickly tired of Kanye’s “unresolved issues.”
Lady Gaga & Christian Carino
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Gaga called off her engagement with former manager Christian because he allegedly was a bit too needy.
Lady Gaga & Christian Carino
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Whispers of jealousy and constant badgering of her were reportedly the reason the Joanne singer pulled the plug.
Rebel Wilson & Jacob Busch
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Before Rebel found love with her current partner, Ramona, she was in a relationship with businessman Jacob Busch.
Rebel Wilson & Jacob Busch
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However, the couple called it a day in early February 2021, allegedly breaking up over text.
Amanda Seyfried & Ryan Phillipe
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These two had a non-serious on-off relationship back in 2011. However, after reconciling briefly, both decided to go their separate ways.
Amanda Seyfried & Ryan Phillipe
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Reportedly the split was amicable, with “no bad blood” between the pair.
Milo Ventimiglia and Hayden Panettiere
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The pair dated for two years after meeting on the set of the show, Heroes, with the eleven-year age gap between the two causing quite a stir.
Milo Ventimiglia and Hayden Panettiere
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Fiercely tight-lipped about their private life together, what went wrong between them has never been revealed. However, milo has since said dating co-workers is a “bad idea.”
Sophia Bush & Austin Nichols
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Sophia has something of a habit of dating her One Tree Hill co-stars. Not only was she married to Chad Michael Murry, but she also dated James Lafferty and Austin Nichols.
Sophia Bush & Austin Nichols
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She dated the latter for six years before the romance met its maker in 2012.
Jude Law & Sienna Miller
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This relationship was wrought with scandal when it was revealed Jude had embarked on an affair with the nanny, Daisy Wright.
Jude Law & Sienna Miller
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The pair split up in late 2005, before reconciling again briefly in 2009, before permanently saying ciao to each other in early Feb 2011.
Nina Dobrev & Austin Stowell
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This couple threw in the dating towel after less than a year, supposedly due to busy work schedules.
Nina Dobrev & Austin Stowell
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The relationship ended in early 2016, with the pair keeping things amicable.
Nick Jonas & Delta Goodrem
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Before Priyanka made an honest man out of Nick, the Jonas Brothers member briefly dated the Aussie songbird, Delta, for ten months, before going their own ways.
Nick Jonas & Delta Goodrem
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Neither party confirmed the reason for the breakup, but their reps stated they wanted to “focus on their careers.”
Hilary Duff & Mike Comrie
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This marriage fizzled out a few years after the pair welcomed their son, Luca. Their divorce was finalized circa Valentine’s Day in 2016.
Hilary Duff & Mike Comrie
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Hilary has spoken candidly about relationship flames fizzling out and has questioned whether monogamy is realistic.
Khloe Kardashian & Tristan Thompson
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These two had engaged in an on-off relationship before calling it a day when Tristan fathered a child with another woman.
Khloe Kardashian & Tristan Thompson
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However, the pair seem to be on good terms, with Khloe even attending Tristan’s mom’s funeral in January 2023.
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