They were meant to be, until they weren’t. Whether it was the whirlwind romance of Ariana Grande and Pete Davidson or the peak ’90s love between Brad Pitt and Gwyneth Paltrow, these romances were time capsules of A-list relationships. Here, the celebrity couples that popped the question but never made it down the aisle.
1 of 67
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.
2 of 67
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.
3 of 67
Cameron Diaz and Jared Leto
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.”
4 of 67
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.”
5 of 67
Kanye West and Alexis Phifer
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.”
6 of 67
Britney Spears and Jason Trawick
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.
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Mark Ronson and Rashida Jones
8 of 67
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!.
9 of 67
Carson Daly and Tara Reid
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.”
10 of 67
Evan Rachel Wood and Marilyn Manson
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.”
11 of 67
Julia Roberts and Dylan McDermott
12 of 67
Jennifer Morrison and Jesse Spencer
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.
13 of 67
Mary-Louise Parker and Jeffrey Dean Morgan
14 of 67
Nick Cannon and Selita Ebanks
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.”
15 of 67
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.
16 of 67
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.
17 of 67
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.
18 of 67
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.”
19 of 67
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.'”
20 of 67
Katie Holmes and Chris Klein
Holmes and the 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.”
21 of 67
Kate Moss and Pete Doherty
The supermodel dated the Libertines frontman on-and-off from 2005 until 2007.
22 of 67
Rose McGowan and Marilyn Manson
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.
23 of 67
Kerry Washington and David Moscow
The Scandal actress dated Moscow for four years, from 2003 until 2007, 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.
24 of 67
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.”
25 of 67
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.
26 of 67
Jay Baruchel and Alison Pill
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.”
27 of 67
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.”
28 of 67
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.
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Robin Wright and Ben Foster
30 of 67
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 in 2017.
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