It’s no secret that the love lives of Hollywood’s elite have included countless whirlwind romances, breakups and makeups. Here’s a list of the celebrity couples who have planned to tie the knot over the years, but never made it down the aisle.
Demi Moore and Emilio Estevez
After co-starring in St. Elmo’s Fire, Demi Moore and Emilio Estevez got engaged in 1985. They had an on-again, off-again relationship for about two years, and even set their wedding date for December 1986, but eventually called it quits. Thirty years later, Moore has three children by now ex-husband Bruce Willis, who she was married to from 1987 to 2000. Estevez has two children by his model ex-wife, Carey Salley. Moore and Estevez remain good friends.
Johnny Depp and Sherilyn Fenn
Starting in 1985, after they met on the set of a student film, actors Sherilyn Fenn and Johnny Depp dated off and on. They were only engaged for a short time before ending the three-year relationship. Fenn married musician Toulouse Holliday in 1994. She has two sons. Depp went on to have a number of other high-profile relationships, including two other engagements.
Johnny Depp and Jennifer Grey
Depp dated Dirty Dancing star Jennifer Grey sometime after her relationship with Matthew Broderick. Although details about the relationship remain uncertain decades later, the couple got engaged in 1989 and broke up about a year later. Due to a serious car accident that occurred before the Grey’s relationship with Depp, she withdrew from the spotlight for awhile. She now lives in California with her husband and daughter.
Johnny Depp and Winona Ryder
Depp met Winona Ryder at a movie premiere in 1990. They dated for five months before getting engaged—Depp told People at the time, “There’s been nothing in my 27 years that’s comparable to the feeling I have with Winona.” He got a tattoo on his arm that wrote “Winona Forever,” but the relationship ended after three years. The tattoo, which has been changed, now says “Wino Forever.” In 2011, Ryder began a relationship with Scott Mackinlay Hahn, a designer. Last year, Depp’s relationship with model-actress Amber Heard made headlines amidst allegations of abuse.
The pair reached a settlement and their divorce was finalized in January 2017.
Kiefer Sutherland and Julia Roberts
At 23, with Pretty Woman, Steel Magnolias, and Sleeping With the Enemy under her belt, Julia Roberts had made a major splash in Hollywood. Enter Kiefer Sutherland, 24, her costar in Flatlines, and in the throws of an unfinished divorce from then-wife Camelia Kath. The pair moved into Roberts’ home in 1990. But by 1991, they were experiencing challenges, including a rumored affair between Sutherland and a local go-go dancer. But even after allegations were made public, Roberts was spotted with an engagement ring.
They planned to marry in June 1991 in front of 150 guests, but cancelled the wedding just three days before they were set to walk down the aisle. Roberts married Daniel Moder in 2002 and they have three children together. Sutherland went on to get married and divorced twice, with a string of other relationships in between.
Kyle MacLachlan and Linda Evangelista
After a couple of other high-profile relationships, Twin Peaks actor Kyle MacLachlan met model Linda Evangelista at a photoshoot in 1992 and they quickly got hot and heavy. She introduced him to the world of fashion and they “had a ball” for six years, during which they got engaged. But they soon when their separate ways: "I didn't really want to get married as I couldn't see the point and the relationship wasn't really going anywhere," MacLachlan told the Evening Standard. He met his current wife, Desiree, while filming Sex and the City.
They have a son together.
Drew Barrymore and Leland Hayward
After success with her iconic role in ET, the details of Drew Barrymore’s personal life remained in the spotlight. Having been granted juvenile emancipation at age 14 and moved into her own apartment by age 15, Barrymore became engaged the following year to then 24-year-old Leland Howard, grandson and namesake of the famed Hollywood producer. Within a few months, the engagement was called off.
Drew Barrymore and Jamie Walters
The following year, Barrymore was engaged to Jamie Walters. They lived together for about a year before breaking up in 1993. Now, over 40 years into a nearly lifelong career, Barrymore continues to land major roles, which she balances with raising her two daughters by ex-husband Will Kopelman.
Sandra Bullock and Tate Donovan
Love Potion No. 9 costars Sandra Bullock and Tate Donovan started dating after filming ended for the 1992 movie. They got engaged, but broke up after three years together. "The person who needed me most was always the person I was attracted to," Bullock old People after the split. "My priorities were him first, me second." Bullock has since gotten married to and divorced from Jesse James, and adopted two children.
Alyssa Milano and Scott Wolf
Alyssa Milano once joked that "[My dating history] is longer than my IMDB [profile]." She has had a number of relationships with other celebs including Justin Timberlake, Eric Dane and David Arquette. But only one of those ended with a broken engagement: her public, fast-moving relationship with Scott Wolf. They met in June 1993 on the set of Double Dragon. Two months later, they moved in together, then got engaged two months after that. But by the following year, they’d both moved on. Now, Milano has a son and a daughter with her agent husband of nearly nine years, David Bugliari.
Wolf married The Real World: New Orleans alum Kelley Marie Limp in 2004, and the couple has three children together.
Brad Pitt and Gwyneth Paltrow
As evidenced by their throwback photos together, Brad Pitt and Gwyneth Paltrow dated in the mid-90’s, when Paltrow was in her early twenties and Pitt was just over thirty. They were together from 1994 to 1997, during which they had a very public engagement. Paltrow called it off because she wasn’t ready for marriage. In 2015, nearly 20 years after the split, she told Us Weekly, “You can't make that decision when you're 22 years old... I wasn't ready, and he was too good for me.” Now she’s raising her daughter and son, and running Goop, a wellness and lifestyle platform.
Pitt has six children with Angelina Jolie, who filed for divorce in 2016, although their split has not been finalized.
Tate Donovan and Jennifer Aniston
On Friends Rachel Greene had a love interest named Joshua. In real life, Jennifer Aniston and Tate Donovan, the actors behind those characters, had been dating for three years before getting engaged in 1998. Their engagement only lasted briefly, but Donovan was cast for his stint as Joshua not long after the break-up. “It was horrible. It was so tough. I remember getting back to my dressing room and just weeping,” Donovan said in a fit of laughter during a 2013 Huffpost interview. In 2015, Aniston married fellow actor Justin Theroux at their home in Bel Air, California.
Marilyn Manson and Rose McGowan
For three and a half years, Rose McGowan shared a very public relationship with Marilyn Manson. But two years into their engagement, the two called it off in 2001 and went their separate ways for good. While it has been speculated that the two broke up because of drug use, McGowan speaks highly of Manson and their relationship: “There is great love,” she explained to Andy Cohen in 2015, “but our lifestyle difference is, unfortunately, even greater.” Manson went on to marry Dita Von Teese, but their marriage ended amid rumors that he was dating Evan Rachel Wood on the side.
Later that year, Mason’s relationship with Wood went public. In 2007, McGowan became engaged to director Robert Rodriguez. That ended in 2009 before their planned wedding date—read on for details.
Jennifer Lopez and Ben Affleck
Some celebrity couples captivate the public eye, and this romance is at the top of that list. It was covered so much that the press and public came to know Jennifer Lopez and Ben Affleck as ‘Bennifer.' They met on the set of Gigli and began dating in 2002. They got engaged after starring in the movie Jersey Girl and Lopez’s music video for Jenny from the Block, but ended up calling it quits in 2004. Lopez now has twins with Marc Anthony, who she reunited with after Bennifer ended, but divorced in 2011.
Affleck went on to marry Jennifer Garner, and the pair had three children together before announcing plans for divorce in 2016 (although paperwork had not been filed at time of publication).
Alanis Morissette and Ryan Reynolds
When these two Canadian stars met at Drew Barrymore’s birthday party in 2002, they really hit it off—so much that they got engaged two years later. In June 2005, a year into their engagement, Morissette said of Reynolds, "He's just such a supportive creature. I feel so loved by him, in a trampoline kind of way. He's always very happy for me." But the pair never set a wedding date, and in February 2007, their reps announced the split. Now they’ve moved on to start beautiful families: Reynolds with Blake Lively and their two daughters; and Morissette with Mario “Souleye” Treadway, their daughter and son.
Sheryl Crow and Lance Armstrong
In 2003, the same year cyclist Lance Armstrong divorced from his wife, he started dating singer Sheryl Crow. Their engagement was made public in September 2005 and lasted until February 2006, when they broke up. Armstrong, already father to three children by his first wife, went on to have two more children with fiancé Anna Hansen, despite beliefs that he could no longer conceive naturally after undergoing treatment for testicular cancer in 1996. Sheryl Crow adopted two sons, in 2007 and 2010. She lives with them in Nashville.
Jennifer Love Hewitt and Ross McCall
Ghost Whisperer star Jennifer Love Hewitt met Scottish actor Ross McCall when he was a guest star on the show. They began dating in late 2005, and got engaged after two years together, while on vacation in Hawaii. The pair reportedly cancelled wedding plans the following year. Hewitt is now married to fellow actor Brian Hallisay and they have two children together.
Kerry Washington and David Moscow
From 2004 to 2007, Scandal leading lady Kerry Washington was engaged to David Moscow, known for his role as young Josh Baskin in the film Big. "When we were planning the wedding, I didn't even feel like picking out a dress," she says. "But I didn't rush things; I let my intuition guide me. We realized that even though we love each other on a very profound level, we were doing emotional gymnastics to try to work things out.” After a very public breakup, Washington has kept her personal life as private as possible, even through her marriage to Nnamdi Asomugha and birth of her daughter and son.
Sienna Miller and Jude Law
After Jude Law's divorce from Sadie Frost, the mother of his first three children, he began a relationship with Alfie co-star Sienna Miller. Law proposed on Christmas Day in 2004. In July 2005, he issued a public apology for engaging in an affair with his children’s nanny. Law and Miller broke things off in November of the following year. They got back together in late 2009, but broke up for good in February 2011. Law has since had two other children from separate relationships. Miller has a daughter with actor Tom Sturridge, although they ended their relationship in 2015.
She started dating director Bennett Miller in 2014 after meeting on set, and was recently spotted wearing an engagement ring—but not for the reason you think!
Marilyn Manson and Evan Rachel Wood
In 2006, at age 18, Evan Rachel Wood met Marilyn Manson at a party in West Hollywood. Manson was married at the time, but he and Wood began dating shortly after. In a 2016 interview with Rolling Stone, Wood said that regardless of their 18-year age difference, she found “somebody that promised freedom and expression and no judgments,” in Manson during their relationship. They dated on and off for four years before Manson proposed onstage in Paris in January 2010. By 2011, they’d split up for good.
Still, Wood said in 2015, “I appreciate everything he taught me. I just don’t think we were right for each other.” Wood shares a son with two-time ex Jamie Bell, and recently called off her engagement to bandmate Zach Villa.
Jeffrey Dean Morgan and Mary-Louise Parker
In December 2006, Mary-Louise Parker and actor Jeffrey Dean Morgan began dating on and off after meeting on the set of Weeds. They got engaged in February 2008, but by April of that year, they’d called it quits. Parker had a son from a previous relationship, and in September 2007, during the span of her relationship with Morgan, she adopted a baby girl from Ethiopia. Morgan went on to start a relationship with actress Hilarie Burton. In 2010, Burton gave birth to a son, Morgan’s only child.
Robin Wright and Ben Foster
After her divorce from Sean Penn in 2010, House of Cards actress Robin Wright began dating actor Ben Foster. The pair announced their engagement in early 2014, but called it off in November of that year. They reconciled and the engagement was back on as of January 2015, but they broke up for good the following August. Foster is now engaged to Orange Is the New Black actress Laura Prepon. They welcomed a daughter in August 2017.
Sean Penn and Charlize Theron
After the end of his 16-year marriage to Robin Wright, Milk film star Sean Penn began dating Charlize Theron in December 2013. After 18 months together—and an engagement a year into the relationship—the actors went their separate ways. Despite rumors about a more complicated ending, Theron told WSJ magazine, “We were in a relationship and then it didn't work anymore. And we both decided to separate. That's it.”
Evan Rachel Wood and Zach Villa
Having met in Los Angeles in 2015, Evan Rachel Wood and Zach Villa quickly hit it off and began recording electro-pop music as a duet they named Rebel and a Basketcase. Although the couple hasn't spoken publicly about the engagement, they arrived at the SAG Awards red carpet in January sporting matching blue suits and subtle engagement bands. People received confirmation of the engagement from Wood's publicist. In early September 2017, the pair announced that the relationship had ended.
Hayden Christiansen and Rachel Bilson
In 2008, the couple met as co-stars on the set of Jumper. They got engaged that December, but quietly called it off in August 2010. By the end of that year, they were back together, having reconciled the differences that broke them up in the first place. On October 29, 2014, they welcomed daughter Briar Rose Christiansen, according to a statement from their rep. After years of keeping the details of their relationship private, they announced in September 2017 that they had officially ended things.
"They are completely, officially done,” a source told Us Weekly at the time of the split.