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They had been meant to be, except they weren’t. Whether or no longer it became the whirlwind romance of Ariana Grande and Pete Davidson or the tip ’90s care for between Brad Pitt and Gwyneth Paltrow, these romances had been time capsules of A-list relationships. Right here, the celeb couples that popped the place a question to but below no conditions made it down the aisle.
1 of 67
Taylor Kinney and Lady Gaga
Fans had been obvious that the singer and Kinney would develop it down the aisle when he popped the place a question to on Valentine’s Day in 2015 after four years of courting. However the outmoded couple announced they had been going their separate programs in June 2016.
2 of 67
Drew Barrymore and Leland Hayward
Drew purchased engaged to Leland Hayward III, grandson of Hollywood producer Leland Hayward, when she became true 16 years outmoded in 1991 sooner than calling it quits that very same twelve months.
3 of 67
Cameron Diaz and Jared Leto
Diaz began courting the 30 Seconds To Mars frontman in 1999 and they purchased engaged in 2000, only to interrupt up three years later. “Or no longer it is a need to to procure any person within the same house as you are. Timing is the whole lot,” Diaz informed Cosmopolitan in 2015. “We ladies assuredly pause the part where we procure the same particular person over and over — they gape and appear various, but deep down, they’re the same. And that’s the reason 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 twelve months of courting, however the actress called it off days sooner than the ceremony became house to purchase house. On the day of their planned wedding, Sutherland became seen enthralling out of the house he shared with Roberts within the Hollywood Hills. “We had determined we wished to earn married, but then this other part roughly took over,” Sutherland stated in an interview with Folk. “She became arguably primarily the most eminent woman within the enviornment, and this wedding that became supposed to be one thing between the 2 of us grew to became one thing so great.”
5 of 67
Kanye West and Alexis Phifer
Earlier than marrying Kim Kardashian, Kanye West dated the style clothier on-and-off since 2002 sooner than getting engaged over a lobster and pasta dinner in Capri in August 2006. They announced their separation two years later. “Or no longer it’s persistently unhappy when issues care for this pause, and we remain associates,” Phifer informed Folk. “I need him the particular in his future and all of his endeavors. He’s one of primarily the most proficient of us I’ve ever met.”
6 of 67
Britney Spears and Jason Trawick
Spears began courting the agent in 2009 when he began representing her. He popped the place a question to on his 40th birthday in December 2011, however the 2 announced they had been calling off the wedding in January 2013.
7 of 67
Price Ronson and Rashida Jones
8 of 67
Jennifer Lopez and Ben Affleck
Frequently frequently called the customary “Bennifer,” Lopez and Affleck met on the house of the 2002 film Gigli and acquired engaged, calling it off in early 2004 sooner than their wedding. “I deem various time various part, who knows what might likely’ve came about, but there became an staunch care for there,” Lopez informed E!.
9 of 67
Carson Daly and Tara Reid
Reid and Daly began courting after meeting on the house of Total Request of Stay in 2000, but called off their wedding in June 2001. “To a degree, I dodged a bullet,” Daly informed ELLE in 2012. “I became getting taking into account my profession, and she wished to shoot movies and true occasion in her fracture day. That did now not work for me.”
10 of 67
Evan Rachel Wood and Marilyn Manson
The actress began courting Manson when she became 19 years outmoded and they grew to became engaged in 2010 but broke it off later that twelve months. “I believed I became in care for,” she stated in an interview with Accumulate-A-Porter.com. “I wasn’t doing it to hide a degree or be rebellious…And he became true what I predominant, because I felt if truth be told free with him. And that freedom became heavenly.”
11 of 67
Julia Roberts and Dylan McDermott
12 of 67
Jennifer Morrison and Jesse Spencer
Morrison began courting her Dwelling co-star in 2004 and Spencer proposed to her at the Eiffel tower in December 2006, but they determined to call off their engagement in August 2007.
13 of 67
Mary-Louise Parker and Jeffrey Dean Morgan
The Weeds co-stars had a two-twelve months on-again, off-again relationship and had been temporarily engaged in 2007 sooner than calling it off in April 2008.
14 of 67
Reduce Cannon and Selita Ebanks
Cannon and the outmoded Victoria’s Secret mannequin purchased engaged in Would possibly maybe fair 2007 but determined to cleave up up 5 months later. “I became very young, he became young,” Banks stated. “The entirety happens for a reason. It taught me plenty, especially with media. Y’all became brutal. I became called the whole lot below the solar for true getting engaged.”
15 of 67
Laura Dern and Billy Bob Thorton
Thorton popped the place a question to in 1998 but they cleave up a twelve months later when the actor allegedly left Dern to marry Angelina Jolie. “I left our house to work on a movie, and whereas I became away, my boyfriend purchased married, and I’ve below no conditions heard from him again,” Dern informed Talk Journal.
16 of 67
Demi Moore and Emilio Estevez
Demi and The Breakfast Club actor met on the house of Wisdom in 1984, getting engaged a twelve months later sooner than parting programs in 1987.
17 of 67
Jude Legislation and Sienna Miller
The actors met on the house of Alfie in 2004 and took their romance off-hide, getting engaged on Christmas Day of that twelve months. In July 2005, Legislation admitted to having an affair with the nanny of his adolescents and the couple cleave up up in 2006.
18 of 67
Gwyneth Paltrow and Brad Pitt
The closing ’90s couple co-starred together within the 1995 film Se7en and hit it off. Later, Pitt proposed however the 2 called in off in 1997. Paltrow later informed Howard Stern, “I became 22 when we met. Or no longer it’s taken me except 40 to earn my head out of my ass. You cannot develop that resolution for those who are 22 years outmoded…I wasn’t ready, and he became too applicable for me. I did now not know what I became doing.”
19 of 67
Brad Pitt and Jill Schoelen
Pitt recalled being dumped by actress Jill Schoelen, whom he became engaged to for three months in 1989. “She called me up in Los Angeles and became crying on the mobile phone. She became lonely and there became an astronomical drama. At this point I had $800 to my name and I spent $600 of it getting a spot from Los Angeles to Hungary to witness her,” Pitt informed The Sun. “I purchased there, went straight to the house where she became filming and that evening we went out to dinner. She informed me that she had fallen in care for with the director of the film. I became so stricken I stated, ‘I’m outta here.'”
20 of 67
Katie Holmes and Chris Klein
Holmes and the American Pie actor purchased engaged in December 2003 after 5 years of courting, but ended issues in March 2005. “From my facet there became a bunch of denial and dismay relating to the long toddle,” Klein informed Folk in 2012. “It ended as amicably as these items can pause.”
21 of 67
Kate Moss and Pete Doherty
The supermodel dated the Libertines frontman on-and-off from 2005 except 2007.
22 of 67
Rose McGowan and Marilyn Manson
McGowan and the rock musician had been engaged from February 1998 except January 2001, with the Charmed actress ending the engagement. “There’s giant care for, but our standard of living distinction is, unfortunately, even larger,” she stated in a observation.
23 of 67
Kerry Washington and David Moscow
The Scandal actress dated Moscow for four years, from 2003 except 2007, and at closing called off their engagement. “Turning 30 became a time after I believed, ‘Wait a 2nd. How grand of my lifestyles if truth be told reflects who I am and who I must be?’ I’ve learned more about myself since leaving that relationship,” Washington informed The Unique York Put up.
24 of 67
Sheryl Crow and Lance Armstrong
The two began courting in 2003 and called it quits in February 2006 after getting engaged 5 months earlier. “It became a applicable scoot,” the cyclist informed Howard Stern. “She’s a giant woman. Obviously it did now not work out, but I deem 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 had been engaged for three years sooner than maintaining apart in Would possibly maybe fair 1995.
26 of 67
Jay Baruchel and Alison Pill
The Canadian stars called off their two-twelve months engagement in March 2013. “By myself again, naturally. Heartbroken,” Baruchel wrote in a Twitter message that he later deleted. “I gained’t be on twitter for awhile gang. Getting dumped rules.”
27 of 67
Sandra Bullock and Tate Donovan
The actress began courting her Like Potion No. 9 in 1992 and they purchased engaged, but cleave up after three years. “The particular person that predominant me most became persistently the particular person I became attracted to,” Bullock informed Folk of the cleave up. “My priorities had been him first, me 2nd.”
28 of 67
Rachel Weisz and Darren Aronofsky
Weisz and the Black Swan director dated for nine years and had a son together sooner than ending their engagement in November 2010.
29 of 67
Robin Wright and Ben Foster
The outmoded couple had been on-and-off again since getting engaged in January 2014 and cleave up for the 2nd time in August 2015.
30 of 67
Dan Aykroyd and Carrie Fisher
The outmoded SNL comedian became engaged to Fisher after proposing to her on the house of their 1980 film The Blues Brothers. They went their separate programs when Fisher reconciled with Paul Simon in 1983. “Throughout the system of her resolution to no longer marry me and wed one other, the reward for my unwavering toughen in whatever resolution she wished to whole became the time I had with her as a relied on buddy and fellow evening hawk,” Aykroyd stated throughout a memorial service for the leisurely actress in 2017.
Savannah Walsh
Editorial Fellow
Savannah Walsh is an Editorial Fellow at ELLE.com.
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