11 Celebrity Engagements That Never Made It To The Altar

Whenever a celebrity begins a new relationship, tabloid interest is always piqued. If that relationship happens to be with another star, then look out — coverage of this celeb-celeb couple is certain to make nonstop rounds. That usually results in cutesy media-derived nicknames — Bennifer, Brangelina, Kimye — while paparazzi lay in wait. As celebrity couples see what semblance of privacy they'd previously enjoyed go out the window, the media scrutiny they experience can become so intense that it's a miracle that any of those couples manage to survive it.

Truth be told, few do. Broken celebrity romances are, sadly, a dime a dozen, as evidenced by some of the most egregiously expensive celebrity divorces in Hollywood. And while divorces are common in Hollywood, there are also those celebrities who don't even make it down the aisle, getting engaged only to call the whole thing off and go their separate ways. 

To find out more about these showbiz romances gone sour, read on for a look at 11 celebrity engagements that never even made it to the altar. 

Winona Ryder was just 18 years old when she spotted 27-year-old Johnny Depp at the 1989 premiere of "Great Balls of Fire," in which she played the teenage bride of rocker Jerry Lee Lewis. As the two told Rolling Stone, theirs was a case of love at first sight. "It was a classic glance, like the zoom lenses in 'West Side Story,' and everything else gets foggy," Depp gushed. "It wasn't a long moment, but it was suspended," Ryder confirmed, with Depp adding, "I knew then."

They got engaged five months later, with Depp celebrating the occasion by getting a tattoo on his bicep reading "Winona Forever." They went on to appear onscreen together, co-starring in "Edward Scissorhands" (directed by Tim Burton, who'd previously worked with Ryder in "Beetlejuice"). For the next few years, Ryder and Depp were young Hollywood's ultimate "it" couple until they broke it off in 1993 (Depp altered his tattoo, which he altered to "Wino Forever").

Depp moved on and, within a year of their split, began dating supermodel Kate Moss. Perhaps because she was nearly a decade younger than her ex, the breakup hit Ryder much harder. She told Elle in 2009 (via the fan site Winona-Ryder.com) that it was her "first real breakup, the first heartbreak. And I think it was really ironic because, like, everybody else just thought I had everything in the world ... everything was sort of at its peak, but inside I was completely lost."

Having both got their starts within the ring as WWE stars, both John Cena and Nikki Bella began dating in 2012. During the course of their relationship, Cena branched out to become a movie star, while Bella and twin sister Brie ventured successfully into reality TV and podcasting. After dating for five years, Cena got down on one knee and popped the question — in the middle of the ring during WrestleMania 33 in April 2017.

They'd only been engaged for a year when Bella decided to end things with her fiancé. "While this decision was a difficult one, we continue to have a great deal of love and respect for one another," the exes said in a joint statement to Us Weekly in April 2018. Cena expressed his disappointment via Instagram, posting a "Simpsons" meme reading "Worst Day Ever." 

In 2020, Bella appeared on Maria Menounos' "Better Together" podcast, where she conceded that she and Cena each had varying visions of life. "Overall, we did have such an incredible relationship, it was just two people that wanted two different lives," she said, as reported by Us Weekly. According to Bella, she wanted to have kids, and he did not — but ultimately agreed to make her happy. "Even in the end when he was willing to give me kids, I could just tell, it's not what he wanted," she recalled. "And that's really, like, you know, what pushed me in the end."

It's not easy for two internationally known celebrities to retain their privacy, so we really need to hand it to Lenny Kravitz and Nicole Kidman. In fact, fans were shocked to discover that the two had had an intense romance and even got engaged — all without anyone knowing. It wasn't until years later, long after she'd married Australian country star Keith Urban that Kidman revealed she and the "Let Love Rule" singer had dated in 2003 and that she'd been his fiancée.

Kidman first dropped that particular bombshell in an interview with Net-A-Porter's magazine The Edit, revealing how she came to know his daughter, Zoë Kravitz. "Well, I knew Zoë because I was engaged to her father," she said, via People. "I love Lenny; he's a great guy."

Previously, Kidman had revealed that they'd gotten engaged at some point in the early 2000s but didn't identify her suitor's name. "It just wasn't right," she revealed in a 2007 Vanity Fair interview, explaining why things ultimately didn't work out. "I wasn't ready," she said. "We weren't ready."

Co-stars in the Brat Pack classic "St. Elmo's Fire," Demi Moore and Emilio Estevez met on the film and soon began dating. "In truth, I liked all my co-stars and remain close to some of them today, but the person who stands out from this period is, of course, Emilio," Moore wrote in her autobiography, "Inside Out: A Memoir." 

Their relationship grew serious, with Moore welcomed into Estevez's family (which included his dad, Martin Sheen, and brother, Charlie Sheen). After about six months together, they got engaged, with Moore moving into Estevez's Malibu home. They set a date for the nuptials and were preparing to walk down the aisle when Moore learned some disturbing information. "Emilio and I had in fact just mailed out the invitations for our wedding when a friend told me she had seen him out with someone else in LA. He denied it, of course, but I was having a hard time trusting him: during a two-week break up a few months before, he'd slept with an 'ex' girlfriend, lied about it, and then been forced to tell me the truth when he found out she was pregnant," she wrote.

Desperate to salvage the relationship, she took the advice of her therapist to bring Estevez in for a joint session. "He was resistant, but he finally did make the trip, and when he revealed his priorities in that session — you'll be surprised to hear — I was pretty low on that list," Moore wrote. "I postponed the wedding indefinitely."

In the mid-1990s, Tate Donovan famously began dating Jennifer Aniston, who was riding high on the success of the hit sitcom "Friends." According to a timeline of the ups and downs of Aniston's love life, she'd previously dated two actors, Charlie Schlatter and Daniel McDonald, as well as Counting Crows frontman Adam Duritz, before getting serious with Donovan. While they never did get engaged, they were living together when they decided to split up — just when Donovan had booked a guest-starring role on "Friends" — awkward!

Prior to his romance with Aniston, Donovan was engaged to another famous actor, Sandra Bullock. They met when they were both cast in a 1992 rom-com, "Love Potion No. 9." They dated for a few years but never did make it down the aisle before eventually splitting up. "I adored Tate so much," Sandra told Vanity Fair of her ex about a year after they parted ways. "It's like they say, there's one person in your life, and Tate and I are closer than any two people I've ever experienced in my life. There's nobody that means more to me, and I know for a fact that I mean the most to him in that certain way."

When Bullock interviewed Aniston in 2020 for Interview, the women revealed that it had been Donovan — described by Bullock as "our former boyfriend" — who'd introduced them to each other. "I say 'our' because you and I both partook of this one human being," said Bullock. "Yes, we did," Aniston responded. "That's a beautiful way of saying it."

In recounting the rise and fall of Ben Affleck and Jennifer Lopez's love story, it all began in 2001, when they co-starred in "Gigli." Lopez was inconveniently still married to second husband, Cris Judd, but filed for divorce. "We didn't try to have a public relationship," Lopez told People of the media attention their relationship generated. "We just happened to be together at the birth of the tabloids, and it was like 'Oh my God.' It was just a lot of pressure." During a November 2002 interview with Diane Sawyer, Lopez revealed they'd gotten engaged, showing off her massive new ring. "It's the most magnificent thing I've ever seen," she said of the 6.1-carat pink diamond, which reportedly set Affleck back $2.5 million. 

The couple, dubbed "Bennifer," set a date in 2003 but then announced the nuptials were being postponed due to a media frenzy. "When we found ourselves seriously contemplating hiring three separate 'decoy brides' at three different locations, we realized that something was awry," the statement explained, as reported by The Age. By January 2004, they'd split up, issuing a statement confirming the engagement was off. 

Just a few months later, she married singer Marc Anthony, welcoming twins before they divorced in 2011. She then moved on with dancer Casper Smart, whom she dated until 2015. Next came MLB legend Alex Rodriguez, with the two getting engaged before breaking up in 2021. Lopez then rekindled her romance with Affleck 20 years later. This time, they did make it to the altar. Sadly, love was not sweeter the second time around; Lopez filed for divorce in August 2024.

Jesse James, known for his reality show "Monster Garage," was famously married to Sandra Bullock. That marriage, of course, flamed out spectacularly when James was caught cheating in 2010, resulting in a quick divorce. It didn't take James long to move on, and he rebound by immediately by taking up with tattoo artist Kat Von D, a celebrity in her own right from TV show "LA Ink." 

In January 2011, the two got engaged. That September, they'd called it off and split up. "I'm so sad because I really love her," James told People (via Glamour), blaming the fact that she filmed her show in Los Angeles while he lived in Texas. "The distance between us was just too much," he explained.

A couple of months later, Von D issued a Facebook post to reveal the real reason behind the split. "Today I encountered the 19th girl to add to the list of people Jesse cheated on me with during this last year," she wrote in her post (as reported by Us Weekly). "I deserve a big fat 'I told you so,' from everyone, and wish I didn't have to say, 'You all were more right than you'll ever know' but you were," she added, one of James' many exes to speak out about him over the years.

It's not hyperbolic to point out that former "Saturday Night Live" star Pete Davidson has cut a wide swath through the Hollywood dating scene, coupling up with the likes of Kate Beckinsale, Margaret Qualley, Kaia Gerber, Phoebe Dynevor, Madeline Cline, and even reality TV queen Kim Kardashian.

Of all his relationships, Davidson only once put a ring on it when he proposed to pint-sized pop star Ariana Grande. The two met on the set of "SNL" in 2014 and began seeing each other in early 2018. They first stepped out as a couple when they attended the Billboard Music Awards together that May, at which time their relationship was described as casual. Around that same time, Davidson broke things off with girlfriend Cazzie David, while Grande did the same with rapper Mac Miller. Within weeks, Davidson got a Grande-style tattoo; just over a week later, People reported that the two had gotten engaged. "They're just two people who found love quickly and make each other happy all the time," a source told the magazine.

Over the next few months, they were closer than close, making their red-carpet debut together at the MTV VMAs in August. Grande even recorded a song in his honor, the aptly titled single "pete davidson." Less than two months later, in mid-October, the whirlwind relationship went off the rails; TMZ was the first to report that they'd called off their engagement. "It was way too much too soon," a source in Grande's camp told People of why they broke up. "It's not shocking to anyone."

When Gwyneth Paltrow began dating Brad Pitt in 1994 after meeting on the set of "Se7en," the two quickly became Hollywood's ultimate power couple, their combined stardom shining bright. After two years of dating, Brad Pitt popped the question in 1996. Paltrow's parents, producer Bruce Paltrow and actor Blythe Danner were thrilled with the actor they assumed would be their future son-in-law. "I'll never forget when we were engaged and he [Bruce] came to me one day, his eyes full of tears, and he said, 'You know, I never really realized what they mean when they say you're gaining a son. Like, I'm gaining a son,'" Pitt said in a 2020 interview with Paltrow's Goop.

Less than six months after getting engaged, Paltrow called it off and broke up with Pitt. Looking back on her decision, decades later, Paltrow admitted her youth had led her to slam on the brakes. "I think I was a kid and I wasn't ready. He was too good for me. I honestly do think, I was too young and didn't know what I was doing," she said during an appearance on "The Howard Stern Show," as reported by Us Weekly. "I mean I was 22 when we met and it's taken me until 40 to get my head out of my ass. You can't make a decision when you're 22 years old."

These days, Ryan Reynolds seems to be happily married to actor Blake Lively — although there are those who've criticized Lively's cringe attempts to make their marriage seem perfect. Prior to his romance with Lively — whom he met on the set of his superhero movie, "Green Lantern" — he'd been engaged to a fellow Canadian, singer Alanis Morissette.

The pair first met at Drew Barrymore's birthday party in 2002. By the following year, they were very much a couple, appearing together on the red carpets of various Hollywood events. They took the relationship to the next level when they got engaged in June 2004. "We have the perfect combination of compatibility and incompatibility that makes the relationship very passionate," Morissette said in an interview with People. "It's perfect. I think it's about stretching each other."

In 2006, reports emerged that they'd split up but proved to be premature when they reconciled. It was not, however, for good. In February 2007, they announced they were calling off the engagement. "Ryan Reynolds and Alanis Morissette have mutually decided to end their engagement," the exes' reps confirmed in a statement to People. "They remain close friends and continue to have the utmost love and admiration for each other." By April, Reynolds moved on with Scarlett Johansson, with whom he tied the knot in September 2008. That marriage did not last long, with the two announcing their separation in December 2010.

Before she got engaged to Kiefer Sutherland in the late 1990s, Julia Roberts had already racked up a few high-profile relationships, having dated Liam Neeson and broken off her engagement to Dylan McDermott. However, it's tough to ignore the irony that Roberts once starred in a movie called "Runaway Bride" when recalling how her relationship with Sutherland came to a screeching halt — days before their would-be wedding, no less. 

Back in 1991, Soundstage 14 at 20th Century Fox studios was being decorated for their wedding, decked out to resemble a lush garden paradise. However, a mere three days before 150 guests were set to show up to watch the two exchange vows, Roberts called the whole thing off while running off to Dublin with actor Jason Patric — one of Sutherland's closest friends. To describe Sutherland as blindsided would be putting it mildly. "Well, what would you think if someone who goes on every talk show and says how much she loves you did something like this? He's shocked," an anonymous friend of the future "24" star told People. Roberts, however, was doing far better, "She's in a positive frame of mind," a source said.

Sutherland could not have been thrilled with the words of an eyewitness on the airplane on which his friend and ex-fiancée flew. As a fellow passenger told the London Daily Mail, Roberts and Patric were "practically making love" during the flight.