50 Celebrity Couples That Almost Got Married
Getting engaged over lobster and pasta apparently doesn't always work out.
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 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.
Diaz began dating the 30 Seconds To Mars frontman in 1999 and they got engaged in 2000, only to break up three years later. "You have to find someone in the same place as you are. Timing is everything," Diaz told Cosmopolitan in 2015. "We girls sometimes do the thing where we pick the same person over and over again - they look and seem different, but deep down, they're the same. And that's on us."
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."
Before marrying Kim Kardashian, Kanye West dated the fashion designer on-and-off since 2002 before getting engaged over a lobster and pasta dinner in Capri in August 2006. They announced their separation two years later. "It's always sad when things like this end, and we remain friends," Phifer told People. "I wish him the best in his future and all of his endeavors. He's one of the most talented people I've ever met."
Spears started dating the agent in 2009 when he started representing her. He popped the question on his 40th birthday in December 2011, but the two announced they were calling off the wedding in January 2013.
Jones was once engaged to the musician and producer, and they dated from 2002 until 2004.
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!.
Reid and Daly began dating after meeting on the set of Total Request Live in 2000, but called off their wedding in June 2001. "To some extent, I dodged a bullet," Daly told ELLE in 2012. "I was getting serious about my career, and she wanted to shoot movies and just party in her time off. That didn't work for me."
The actress began dating Manson when she was 19 years old and they became engaged in 2010 but broke it off later that year. "I thought I was in love," she said in an interview with Net-A-Porter.com. "I wasn't doing it to prove a point or be rebellious...And he was just what I needed, because I felt really free with him. And that freedom was attractive."
The actress got engaged to her Steel Magnolias co-star after meeting in 1998 but reportedly called off the relationship to date Kiefer Sutherland.
Morrison began dating her House co-star in 2004 and Spencer proposed to her at the Eiffel tower in December 2006, but they decided to call off their engagement in August 2007.
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.
Cannon and the former Victoria's Secret model got engaged in May 2007 but decided to split up five months later. "I was very young, he was young," Banks said. "Everything happens for a reason. It taught me a lot, especially with media. Y'all was brutal. I was called everything under the sun for just getting engaged."
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.
Demi and The Breakfast Club actor met on the set of Wisdom in 1984, getting engaged a year later before parting ways in 1987.
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.
The ultimate '90s couple co-starred together in the 1995 film Se7en and hit it off. Later, Pitt propose,d 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."
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.'"
Holmes and 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."
The supermodel dated the Libertines frontman on-and-off from 2005 until 2007.
McGowan and the rock musician were engaged from February 1998 until January 2001, with the Charmed actress ending the engagement. "There is great love, but our lifestyle difference is, unfortunately, even greater," she said in a statement.
The Scandal actress dated Moscow for four years, from 2003 until 2009, and eventually called off their engagement. "Turning 30 was a time when I thought, 'Wait a second. How much of my life really reflects who I am and who I want to be?' I've learned more about myself since leaving that relationship," Washington told The New York Post.
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."
The actors dated for six years starting in 1990 and were engaged for three years before separating in May 1995.
The Canadian stars called off their two-year engagement in March 2013. "Alone again, naturally. Heartbroken," Baruchel wrote in a Twitter message that he later deleted. "I won't be on twitter for awhile gang. Getting dumped rules."
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."
Weisz and the Black Swan director dated for nine years and had a son together before ending their engagement in November 2010.
The former couple were on-and-off again since getting engaged in January 2014 and split for the second time in August 2015.
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.
The singer and casino mogul announced they were engaged in January 2010 only to call off the wedding later that year in October.
The actors began their romance on set of the 1998 film Slow Burn and got engaged in April of that same year but Driver called off their three-year relationship in October 2001.
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.
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.
They starred in two Jurassic Park films together and were engaged from 1995 until 1997.
The couple met on Twitter and began dating in 2013, getting engaged that October. The rapper then called off their engagement in April 2014. "I learned that I was no longer getting married from the internet, and at the same time as the rest of the world," Rivera wrote in her autobiography Sorry Not Sorry. "Not only were we no longer getting married, but apparently we weren't even together anymore."
"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")
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.
Kravitz and the Victoria's Secret angel dated from 2001 until 2003, getting engaged in the spring of 2002. "I'm going around the world, all these beautiful places, and I'm not taking a walk in the park, I'm not going to the museum - I'm just shut in this depressing-ass room that doesn't belong to me," the musician told Rolling Stone in 2004. "I was engaged to this girl, it didn't work out - this was all at the same time. I think there was a lot of guilt involved from being successful."
The Orange is The New Black actress and photographer were together for two years and announced their engagement in March 2014. They called off their wedding a year and a half later.
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.
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."
The two met in 2005 when Pike was starring in Pride and Prejudice (and when Wright served as director for the film.) He proposed in 2007 two days before the Venice Film Festival but they parted ways in June 2008.
Saldana split from the entrepreneur Keith Britton in November 2011 after 11 years together. They had previously announced their engagement in June 2010.
They were both heirs and both named Paris but they just weren't meant to be husband and wife. In May 2005, Latsis proposed to Hilton after a year of dating but it was announced that the engagement was off in September 2005.
The pop singers began dating in December 2011 and Malik proposed two years later. Their relationship ended in August 2015 with an alleged text message (which Malik later denied). "It was horrible, the worst time in my life," Edwards said. "A four-year relationship, two year engagement ended by a simple text message. Just like that."
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.
The 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.
Depp and the Dirty Dancing star got engaged in 1989 only to split up one year later.
The two got engaged in June 2015 after dating for a year and a half, but in March 2016, months before their wedding, a video of Young surfaced where he admitted he had cheated on Azalea. Azalea announced on Twitter in June 2016 that she found a second video of him cheating.. "I broke up with Nick because I found out he had brought other women into our home while I was away and caught them on the security footage," she wrote.
Getting engaged over lobster and pasta apparently doesn't always work out.
Getting engaged over lobster and pasta apparently doesn't always work out.
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