50 Celebrity Couples That Almost Got Married

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."