25 Celebrities Who Broke Off Their Engagement Inline
Photo: Getty Images1/25Mariah Carey and James Packer
After receiving a whopping 35-carat diamond from Packer in January of this year, by October, news circulated that the pair were on “a break.” They reportedly split over issues surrounding Carey’s reality show and her lavish spending.
Photo: Getty Images2/25Winona Ryder and Johnny Depp
The pair began dating in 1989 when he was 27 and she was just 18, and they were engaged five months after their first date. The relationship resulted in Depp’s somewhat infamous “Winona Forever” tattoo. In 1993, they announced the engagement was off, and the tattoo was changed to “Wino Forever.”
Photo: Getty Images3/25Miley Cyrus and Liam Hemsworth
The couple met in 2009 on the set of The Last Song and reportedly broke up and made up a few times before announcing their engagement in 2012. In 2013, they called it off, but three years later, it seems the engagement is back on—Cyrus has been seen wearing her ring again.
Photo: Getty Images4/25Sienna Miller and Jude Law
The pair was engaged in 2004, but called it quits seven months later after it was revealed that Law had an affair with his children’s nanny. They rekindled their romance briefly in 2010, but have since parted ways again.
Photo: Getty Images5/25Demi Moore and Emilio Estevez
The two met on the set of St Elmo’s Fire in 1984 and were briefly engaged. They eventually decided to call it quits, and Moore began seeing Bruce Willis in 1987.
Photo: Getty Images6/25Emily Blunt and Michael Buble
The pair were engaged in 2005—he even wrote a song, Everything, about her—but the couple parted ways three years later. Differing schedules were said to be to blame, but there were also rumors of his infidelity.
Photo: Getty Images7/25Paris Latsis and Paris Hilton
Paris and Paris, both heirs to family fortunes, were engaged in May 2005 (she received a 24-carat ring), but the two split just months later.
Photo: Getty Images8/25Lance Armstrong and Sheryl Crow
The pair began dating in 2003, got engaged in August 2005, and then rather quickly ended their engagement in 2006. Armstrong later said that he called it quits because Crow wanted to have children and he wasn’t ready.
Photo: Getty Images9/25Evan Rachel Wood and Marilyn Manson
The couple called off their 2010 engagement after only seven months, perhaps not a surprise as they had been on and off again several times before.
Photo: Getty Images10/25Rose McGowan and Marilyn Manson
Manson makes a second appearance on this list—he and McGowan called off their two-year engagement in 2001. McGowan released a statement at the time reading: “There is great love, but our lifestyle difference is, unfortunately, even greater.”
Photo: Getty Images11/25Rose McGowan and Robert Rodriguez
McGowan is another celebrity to make a second appearance on this list, calling off her engagement to Rodriguez in 2009 after the pair began dating more than two years earlier.
Photo: Getty Images12/25Rachel Bilson and Hayden Christensen
After meeting on set and getting engaged a year later in December 2008, Christensen and Bilson called off their engagement in September 2016. The reason for the breakup is still unclear.
Photo: Getty Images13/25Rashida Jones and Mark Ronson
The actress was once engaged to music maestro Ronson. He proposed to her on her 27th birthday, but sadly, things ended just a year later.
Photo: Getty Images14/25Gwyneth Paltrow and Brad Pitt
Before there was Angie and even before there was Jen, there was Gwyneth. Pitt proposed in 1996 after dating for nearly two years. They broke up for good in 1997.
Photo: Getty Images15/25Alexis Pheiffer and Kanye West
The couple were on and off for six years, starting in 2002. A year and a half after getting engaged in Capri, they split in 2008.
Photo: Getty Images16/25Julia Roberts and Kiefer Sutherland
The Hollywood couple was engaged when they were both in their early 20s, and it was Roberts who ultimately ended things—she called off the wedding three days beforehand and took off with Sutherland’s good friend in 1991.
Photo: Getty Images17/25Alanis Morissette and Ryan Reynolds
Reynolds began dating singer Morisette in 2002 and proposed in 2004. They were engaged for nearly four years before finally calling it quits.
Photo: Getty Images18/25Katie Holmes and Chris Klein
The couple began dating in 2000 and were engaged three years later, but finally ended the relationship in 2005.
Photo: Getty Images19/25Britney Spears and Jason Trawick
In late September this year, Spears and Trawick split up after getting engaged more than a year earlier. They first got together in 2009 after Trawick had initially served as her agent.
Photo: Getty Images20/25Rachel Weisz and Darren Aronofsky
The couple was engaged for five years before finally splitting in 2010. The pair had been together for nine years and have a son together, born in May 2006.
Photo: Getty Images21/25Kate Moss and Pete Doherty
The rock star and his on-again-off-again girlfriend went through some seriously wild times in their three years together. It’s not exactly clear if they were engaged or not, but he said as much onstage one night at a concert in 2007—calling Moss his fiancée. They split for good in 2007.
Photo: Getty Images22/25Jennifer Lopez and Ben Affleck
This couple met on the set of their box-office bomb Gigli in 2002 and became engaged that same year. Affleck proposed with a massive pink diamond ring, but it didn’t last, and they broke up in 2004.
Photo: Getty Images23/25Megan Fox and Brian Austin Green
Fox and Green were first engaged in 2006 and ended up calling it quits in 2009. A year later, they were engaged again and eventually married. Last year, Fox filed for divorce, but then they reconciled yet again in April 2016.
Photo: Rex24/25Perrie Edwards and Zayn Malik
The two had been together for more than a year when Malik proposed in 2013. The engagement lasted just shy of two years before they called it off in 2015.
Photo: Getty Images25/25Emma Roberts and Evan Peters
This tumultuous on-again-off-again couple met in 2012 and got engaged in 2014, only to call it off a year and a half later. They rekindled their romance briefly a few months later, but have since called it quits again.
