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29 Celebrity Couples That Almost Got Married
Looking back at all the celebrity pairings that never made it down the aisle.
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They were meant to be, until they weren't. Here, the celebrity couples that popped the question but never made it down the aisle.

Taylor Kinney and Lady Gaga


Fans were sure that the singer and Kinney would make it down the aisle when he popped the question on Valentine's Day in 2015 after four years of dating, but the former couple announced they were going their separate ways in June 2016.

Drew Barrymore and Leland Hayward


Drew got engaged to Leland Hayward III, grandson of Hollywood producer Leland Hayward, when she was just 16 years old in 1991 before calling it quits that same year.

Julia Roberts and Kiefer Sutherland


Roberts and her Flatliners co-star almost made it down the aisle in June 1991 after a year of dating, but the actress called it off days before the ceremony was set to take place. On the day of their planned wedding, Sutherland was spotted moving out of the home he shared with Roberts in the Hollywood Hills. "We had decided we wanted to get married, but then this other thing kind of took over," Sutherland said in an interview with People. "She was arguably the most famous woman in the world, and this wedding that was supposed to be something between the two of us became something so big."

Mark Ronson and Rashida Jones


Jones was once engaged to the musician and producer, and they dated from 2002 until 2004.

Jennifer Lopez and Ben Affleck


Also known as the original "Bennifer," Lopez and Affleck met on the set of the 2002 film Gigli and got engaged, calling it off in early 2004 before their wedding. "I think different time different thing, who knows what could've happened, but there was a genuine love there," Lopez told E!

Julia Roberts and Dylan McDermott


The actress got engaged to her Steel Magnolias co-star after meeting in 1998 but reportedly called off the relationship to date Kiefer Sutherland.

Mary-Louise Parker and Jeffrey Dean Morgan


The Weeds co-stars had a two-year on-again, off-again relationship and were briefly engaged in 2007 before calling it off in April 2008.

Laura Dern and Billy Bob Thorton


Thorton popped the question in 1998 but they split a year later when the actor allegedly left Dern to marry Angelina Jolie. "I left our home to work on a movie, and while I was away, my boyfriend got married, and I've never heard from him again," Dern told Talk Magazine.

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Demi Moore and Emilio Estevez


Demi and The Breakfast Club actor met on the set of Wisdom in 1984, getting engaged a year later before parting ways in 1987.

Jude Law and Sienna Miller

The actors met on the set of Alfie in 2004 and took their romance off-screen, getting engaged on Christmas Day of that year. In July 2005, Law admitted to having an affair with the nanny of his children and the couple split up in 2006.

Gwyneth Paltrow and Brad Pitt

The ultimate '90s couple co-starred together in the 1995 film Se7en and hit it off. Later, Pitt proposed, but the two called in off in 1997. Paltrow later told Howard Stern, "I was 22 when we met. It's taken me until 40 to get my head out of my ass. You can't make that decision when you're 22 years old . . . I wasn't ready, and he was too good for me. I didn't know what I was doing."

Brad Pitt and Jill Schoelen

Pitt recalled being dumped by actress Jill Schoelen, whom he was engaged to for three months in 1989. "She called me up in Los Angeles and was crying on the phone. She was lonely and there was a huge drama. At this point I had $800 to my name and I spent $600 of it getting a ticket from Los Angeles to Hungary to see her," Pitt told The Sun. "I got there, went straight to the set where she was filming and that night we went out to dinner. She told me that she had fallen in love with the director of the film. I was so shocked I said, 'I'm outta here.'"

Katie Holmes and Chris Klein

Holmes and data-redactor-tag="em" data-verified="redactor">American Pie actor got engaged in December 2003 after five years of dating but ended things in March 2005. "From my side there was a lot of denial and fear about the future," Klein told People in 2012. "It ended as amicably as these things can end."

Sheryl Crow and Lance Armstrong

The two started dating in 2003 and called it quits in February 2006 after getting engaged five months earlier. "It was a good ride," the cyclist told Howard Stern. "She's a great lady. Obviously it didn't work out, but I think and I hope she's happy. I'm happy."

Ben Stiller and Jeanne Tripplehorn

The actors dated for six years starting in 1990 and were engaged for three years before separating in May 1995.

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Sandra Bullock and Tate Donovan

The actress started dating her Love Potion No. 9 in 1992 and they got engaged, but split after three years. "The person who needed me most was always the person I was attracted to," Bullock told People of the split. "My priorities were him first, me second."

Rachel Weisz and Darren Aronofsky

Weisz and the Black Swan director dated for nine years and had a son together before ending their engagement in November 2010.

Robin Wright and Ben Foster

The former couple were on-and-off again since getting engaged in January 2014 and split for the second time in August 2015.

Dan Aykroyd and Carrie Fisher

The former SNL comedian was engaged to Fisher after proposing to her on the set of their 1980 film The Blues Brothers. They went their separate ways when Fisher reconciled with Paul Simon in 1983. "Throughout the process of her decision to not marry me and wed another, the reward for my unwavering support in whatever decision she wanted to do was the time I had with her as a trusted friend and fellow night hawk," Aykroyd said during a memorial service for the late actress last year.

Evan Peters and Emma Roberts

The on-and-off pair started dating after meeting on the set of their 2012 film Adult World. Peters proposed over the holidays in 2013 but they broke things off in June 2015. They reportedly got back together in November 2016.

Drew Barrymore and Jamie Walters

Barrymore struck up a romance with singer-actor Jamie Walters in March 1992 and they were also briefly engaged until breaking up in November 1993.

Laura Dern and Jeff Goldblum

They starred in two Jurassic Park films together and were engaged from 1995 until 1997.

Johnny Depp and Winona Ryder


"There's been nothing in my 27 years that's comparable to the feeling I have with Winona," Depp told People after meeting Ryder at a film premiere in 1990. The couple would go on to co-star in Edward Scissorhands together and got engaged five months later but eventually split in June 1993. As a declaration of his love for the actress, Depp famously got a "Winona Forever" tattoo (which he later changed to "Wino Forever").

Lenny Kravitz and Nicole Kidman


The musician and actress were once engaged in 2003 but called things off. "It just wasn't right," Kidman told Vanity Fair in 2007. "I wasn't ready. We weren't ready." She would later go on to co-star with Kravitz's daughter Zoe in Big Little Lies.

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Ryan Reynolds and Alanis Morrisette


The Canadian singer and the Canadian actor met in 2002 and hit it off. Reynolds proposed, but they never made it down the aisle, parting ways in 2006.

Emily Blunt and Michael Buble


The couple split in 2008 after three years together. "I was a jerk and I was careless and reckless with the hearts of women I was with," Buble said. "And I got my karma. I earned it. I got my butt and heart kicked and it hurt me enough that I looked in the mirror and I didn't want it to happen again."

Daniel Craig and Satsuki Mitchell


The James Bond actor proposed in 2007 after six years together but the wedding was called off in 2011 just before Craig married Rachel Weisz. "We heard about it like everyone else, by reading the newspapers," Mitchell's father said.

Ginnifer Goodwin and Joey Kern


Once Upon A Time actress got engaged to Kern in 2010 after being set up by a mutual friend but they broke things off in May 2011.

Johnny Depp and Jennifer Grey


Depp and the Dirty Dancing star got engaged in 1989 only to split up one year later.

This story originally appeared on Townandcountrymag.com.
* Minor edits have been made by the Townandcountry.ph editors.

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