We all know that the love lives of Hollywood’s elite are filled with countless whirlwind romances, breakups and makeups. In this article, we have a list of 24 celebrity couples who had planned to tie the knot over the years, but never made it down the aisle. Some you may remember as big time love stories that fizzled quietly, others may have totally gone under your radar.
1. Johnny Depp and Winona Ryder
Best couple of all time. The famous actors began dating after meeting at the New York premiere of Great Balls of Fire! in 1998 when he was 27 and she was 18. They went on their first date two months later. ‘There’s been nothing in my 27 years that’s comparable to the feeling I have with Winona,’ Depp, 54, once told PEOPLE after meeting Ryder. The couple had a very complicated and highly publicized relationship. They got engaged five months after their first date, and Depp even got a tattoo on his right arm, that read ‘Winona Forever.’ They were together for four years and were engaged from 1990 until 1993.
2. Brad Pitt and Gwyneth Paltrow
One of Brad Pitt’s most high profile relationships was with the actress Gwyneth Paltrow in 1994. The famous actors dated from 1994 to 1997 and starred together in the 1995 film Se7en. Paltrow, now 45, was in her early 20s when she was engaged to Brad who is now 53. The actress spoke candidly about her relationship with Brad in an interview last year: ‘I wasn’t ready, and he was too good for me.’ ‘I was such a kid, I was 22 when we met. It’s taken me until 40 to get my head out of my ass.’ she explained.
3. Jennifer Lopez and Ben Affleck
On the set of the mobster comedy Gigli, the 45-year-old actor Ben Affleck met Jennifer Lopez, 48. And so, the super couple known as Bennifer was born. These two stars got engaged in 2002, after Affleck gave Lopez a $2.5 million diamond engagement ring. They planned to wed in an elaborate ceremony in Santa Barbara, California, on Sept. 14, 2003, but unfortunately Affleck called off the festivities with four days’ notice as a result of ‘excessive media attention’. A few months later, the couple officially announced their split.
‘I don’t think I had ever been heartbroken in that way before,’ Lopez later told VH1. ‘I had so many hopes and dreams on something.’
4. Kanye West and Amber Rose
Before there was a Kim Kardashian, there was an Amber Rose. The 33-year-old TV personality was spotted by rapper Kanye West, 40, in the music video What Them Girls Like. They began a romantic relationship that lasted from 2008 to 2010. Since their split, Amber has made several venomous attacks on Kim Kardashian, 36, who is now Kanye’s wife.
‘He is your typical rapper in the industry,’ Amber told The Post. ‘He can’t be faithful, and it’s not just with one person. He’s just unfaithful with a lot of different women.’
5. Sheryl Crow and Lance Armstrong
The 46-year-old cyclist Lance Armstrong, and the 55-year-old pop singer Sheryl Crow, ended their five-month engagement in February 2006. During an interview with Howard Stern almost 7 months ago, the cyclist admitted that it was ‘tough’ being a power couple. ‘Yeah, it was a roll, man,’ Armstrong told Stern when asked if his head got big when he was dating the country superstar in the early 2000s. ‘It was a good ride. She’s a great lady. Obviously it didn’t work out, but I think and I hope she’s happy. I’m happy, but yeah … I watched the Grammys the other day … and we were like presenters at the Grammys … And at the time, I was like, ‘I’ve got to go do what?’ [It was surreal].”
6. Courtney Love and Edward Norton
Courtney Love’s post Cobain metamorphosis into a ‘serious movie star’ came complete with a respectably, educated and classy new boyfriend: Edward Norton. Back then, people were shocked to see the rock singer in a brand new serious relationship: she would always be Kurt Cobain’s girl in everyone’s eye. In 1994, the lead singer of the popular band Nirvana, Kurt, allegedly committed suicide, leaving his two-year-old daughter he had with Courtney, without a father. However, while filming The People vs. Larry Flynt in 1995, the 53-year-old Courtney met actor Edward Norton, 48. The pair dated for four years and were reportedly engaged at one point. She once told The Sunday Times Magazine: ‘I left Ed Norton, who was good and wonderful, for an average bad man who was in A&R. It’s upsetting.’
7. Alanis Morissette and Ryan Reynolds
The 43-year-old rock singer Alanis Morissette started dating the famous 40 year-old-actor Ryan Reynolds in 2002. However, these two never made it down the aisle. In fact, they hadn’t even set a wedding date when they split in February 2007. The news of their split was confirmed in a joint statement by their representatives.
8. Miley Cyrus and Liam Hemsworth
The 24-year-old famous singer, Miley Cyrus met fiancé Liam Hemsworth, 27, on the set of The Last Song in June, 2009. After three years of having an on-again, off-again relationship, the couple announced their engagement in June 2012 but ended it in September 2013. However, in an interview on The Ellen DeGeneres Show in October 2016, Cyrus confessed that they were, once again, engaged. During a recent interview with Howard Stern, The Wrecking Ball singer revealed details about their split, saying: ‘I had to. I don’t like when relationships are two halves trying to make a whole.’
9. Tara Reid and Carson Daly
Love hurts. The 41-year-old actress, Tara Reid, was so broken up by her split from MTV’s Carson Daly, 44, that she ‘couldn’t eat and sought guidance from five therapists’, according to CosmoGirl magazine. The couple started dating in March 2000, after meeting on the set of Total Request Live. They shared an apartment in New York City and Daly proposed on October 29th. Unfortunately, in June 2001, Reid and Daly broke off their engagement.
10. Kiefer Sutherland and Julia Roberts
The stars met on the set of the 1990 flick Flatliners, and subsequently got engaged. They were set to wed during the summer of 1991 before Roberts suddenly called off the wedding just days before it was set to take place. ‘We were young and we were both very much in love,’ the 50-year-old told People magazine‘s Jess Cagle during an interview. ‘We had decided we wanted to get married, but then this other thing kind of took over. 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.’
11. Katie Holmes and Chris Klein
The 38-year-old actor began dating Holmes, also 38, in 2000 and proposed to her three years later, but the romance fizzled out a year later, and the former couple split in March, 2005. In a candid new interview with People magazine, Klein said: ‘We found comfort in one another… We had a similar upbringing and we were going through the same experience (in Hollywood). As the teenage craze came to an end, we found that our relationship was changing as well. From my side there was a lot of denial and fear about the future. It ended as amicably as these things can end.’ The couple was trying to keep the break-up under wraps when Holmes began quietly dating actor Tom Cruise.
12. Courteney Cox and Michael Keaton
Courtney Cox, the 53-year-old actress best known for her role as Monica Geller in Friends, dated Michael Keaton, 66, for six years until their split in 1995. Cox told People magazine shortly after the split: ‘It’s the most important relationship I’ve ever had, and I think he’s the most wonderful person I’ve ever met.’
13. Evan Rachel Wood and Marilyn Manson
The Westworld actress, 30, met Manson, 48, at a party at West Hollywood’s Chateau Marmont in 2006 when she was just 18 years old. Not long after, Wood and Manson, who was married to Dita Von Teese at the time — began dating. In 2007, he divorced the burlesque dancer, now 45, and pursued his relationship with Wood. In early January, 2010, it was reported that the couple was engaged to be married. However, they ended their engagement later that year.
14. Emilio Estevez and Demi Moore
The 54-year-old actress, Demi Moore had an on-again, off-again relationship for about 2 years with actor Emilio Estevez, 55. They got engaged in 1985 after starring in St. Elmo’s Fire together, a film that helped launch both of their careers. They split in 1987 without ever tying the knot.
15. Sienna Miller and Jude Law
The Golden Globe nominee and her Alfie co-star were on the road to marriage in 2004, but a year after their Christmas engagement, Law, 44, publicly apologized to the actress after reports surfaced that he had been having an affair with his nanny. The couple subsequently split in 2006. The two tried to rekindle their romance in 2009, only to break up again by 2011.
16. Laura Dern and Billy Bob Thornton
Thornton, 62, and Dern, 50, shared a dog and lived together when they dated from 1997 to 1999. Nevertheless, he called off their engagement, famously dumping her for Angelina Jolie, 42, just months later.
17. Nicole Richie and DJ AM
The 36-year-old reality star, Nicole Richie, had an on-again, off-again relationship with DJ Adam Goldstei, who unfortunately passed away in 2009. They’d been together from 2003 to 2005 but broke up after a nine-month engagement.
18. Kate Moss and Pete Doherty
The 36-year-old supermodel, Kate Moss, was in a relationship with rock singer Pete Doherty, 38. She first met him at her 31st birthday party in January, 2005. In April, 2007, Doherty announced Moss as his fiancée during one of his concerts in London, at which Moss also performed. In July, 2007, the couple split.
19. Nicollette Sheridan and Michael Bolton
Nicollette Sheridan, 53, famous for her role of Edie Britt in the series Desperate Housewives, had a five year relationship with the 64-year-old rock singer Michael Bolton. The started dating in 1992, but split in 1997. Yet, in 2005, Sheridan returned to him once again years later. In March, 2006, they announced their engagement, but broke it off in August 2008.
20. Jennifer Morrison and Jesse Spencer
House co-stars Jennifer Morrison, 38, and Jesse Spencer, also 38, called off their engagement in 2007 with a statement that read, ‘After much consideration, we have decided not to get married.’ They began dating in 2004 and on December 23, 2006, Spencer proposed to her at the Eiffel Tower.
21. Rachel Weisz and Darren Aronofsky
In the summer of 2001, the stunning 47-year-old actress, Rachel Weisz, began dating American filmmaker and producer Darren Aronofsky. They met backstage at London’s Almeida Theatre, where she was starring in The Shape of Things. The actress moved to New York with Aronofsky the following year. In 2005, they were engaged and their first son, Henry Chance Aronofsky, was born in 2006. In November, 2010, the couple announced they had been apart for months, but remained close friends.
22. Heather Locklear and Jack Wagner
More than a decade after co-starring on Melrose Place, the 56-year-old actress Heather Locklear and her fiancée, the soap opera actor Jack Wagner, 58, called off their engagement in 2011.
23. Alec Baldwin and Janine Turner
When Janine Turner, 54, was 20 years old, she was a young actress eager to hone her craft and make a name for herself beyond daytime soap operas. During an audition she had after her brief role on General Hospital, Janine read with another young actor, Alec Baldwin, 59. Though she remained focused during the audition, Janine didn’t get the part.
‘I asked why I didn’t get the part, and they said, ‘Alec was so taken with you, he couldn’t concentrate!’’ Turner recalled on “Oprah: Where Are They Now?”, laughing. ‘So, I lost the part! But Alec was very persistent.’ Soon, the two fell in love. ‘I was a good ol’ Baptist Texas girl, so we became engaged,’ Turner said. However, Turner and Baldwin never made it down the aisle. “We had the dress, the invitations, the church, everything,” she says. ‘And then we called it off. Mutually called it off.’
At the time, Turner was completely heartbroken over the split. ‘I loved Alec very much, so it was devastating,’ she says. ‘[But] we both just knew that it was wrong… It wasn’t healthy. And I knew I didn’t want to live that way in my life.’
24. Allison Pill and Jay Baruchel
After meeting on the set of Goon, Allison Pill, 31, and and Jay Baruchel, 35, got engaged in 2010. They ended up calling it quits in 2013.