Celeb Engagements That Never Made It to the Altar

Demi Moore and Emilio Estevez fell for each other while starring together in St. Elmo’s Fire, the film that put them on the map and dubbed them as members of the “Brat Pack” back in 1985. They quickly became engaged with plans to wed in December of 1986, but sadly, the couple never made it down the aisle. Moore married Bruce Willis in November of the following year. After her divorce from Willis in 2000, Moore would go on to famously date Ashton Kutcher, whom she married in 2005 and divorced by 2013. She reveals details about all of her relationships in her memoir, Inside Out.

Alyssa Milano openly and humorously admits that she has dated a lot of celebrities. But one you may not be aware of is her short-lived engagement to fellow actor Scott Wolf. The two stars met in 1993 while filming Double Dragon, and they were not at all shy about their feelings towards one another in the public eye. They moved in together after only two months of dating, leading Wolf to propose two months later. Sadly, the nuptials never came to life, and both actors went their separate ways amicably.

Perhaps one of the most memorable engagements of 2018 was that of Ariana Grande and Pete Davidson. As the story goes, the two met over Grande’s various SNL appearances, and on one fateful night in May, the most unlikely couple began dating. It was merely weeks after both celebs had broken things off with their former flames, dubbing them the ultimate rebound relationship. The star-crossed lovers had a very brief and very public courtship followed by an engagement that ended well before it started. After five months of sharing tattoos, Instagram comments and PDA, Grande and Davidson went their separate ways and moved on with other people.

One of Brad Pitt’s most famous relationships came to be in 1994 when he began dating Gwyneth Paltrow. The pair met while filing Seven and got engaged in 1996. That same year, Pitt would famously call Paltrow the “love of his life” during his Best Supporting Actor acceptance speech for his role in 12 Monkeys at the Golden Globes. The couple solidified themselves as one of the most popular couples of the '90s, but unfortunately, it wasn’t enough to keep their love alive. The beloved couple went their separate ways in 1997 before they could make it official. Of course, Pitt would continue to make headlines when it came to his relationships with ex Jennifer Aniston and Angelina Jolie, respectively.

Vanderpump Rules star Lala Kent and movie producer Randall Emmett first met in 2015, and the pair was engaged in 2018. While they had initially planned a wedding for 2020, it never happened — though the couple did welcome a daughter, Ocean, in March 2021. Later in 2021, the couple officially split amid, as Kent later explained on Instagram, alleged cheating.

While they've made us believe in love again in recent months, Bennifer's original go ended with a broken engagement. What happened in the early 2000s? Apparently, the rise in tabloid culture this side of the pond killed what could have been for one of Hollywood’s favourite couples. These former lovebirds met while filming, Gigli in 2003, and found themselves engaged under the spotlight of a media frenzy. Lopez and Affleck were genuinely in love with each other, and they tried desperately to hide from the cameras, even going as far as to stage multiple fake weddings just to peacefully participate in their own. In the end, it was the pressure from the public that stopped the couple from committing to a life of happily ever after.

It was 1992 when Alanis Morissette and Ryan Reynolds allegedly met at Drew Barrymore's birthday party; they were engaged by 2004. This curiously cute Canadian couple garnered attention wherever they went, making it entirely possible that the publics' keen interest in their personal life largely contributed to their end. After a nearly three-year engagement, the couple released a mutual statement announcing their split, with the inevitable claim that “they remain close friends.” In 2008, Morissette released her seventh studio album Flavors of Entanglement, which is reportedly about the couple's relationship and subsequent breakup.

In 2014, Twilight fans nearly lost their collective minds upon discovery of the romantic relationship between Robert Pattinson and FKA Twigs. And while most were delighted by this coupling, many fans were still hanging on to the delusion that Kristen Stewart would swoop back in and claim her vampire. Instead, fans were sent into ANOTHER frenzy over the news that Pattinson and Twigs were engaged to be married. What followed was a string of ugliness that included racist bullying towards Twigs online, tabloid stories of Pattinson being linked to Katy Perry, and accusations that Twigs was canoodling with a male model. Suffice to say — this couple never made it to the altar.

A few years after Nicole Kidman’s divorce from Tom Cruise, she began a discrete relationship that included a very secret engagement with Lenny Kravitz. This all went down in 2002, but the few details the former couple has shared didn’t make their way to public consumption until 2007 when Kidman revealed to Vanity Fair that she was in a secret engagement prior to her commitment to her current husband, Keith Urban. Both Kidman and Kravitz have expressed nothing but love and respect for one another, claiming that the relationship just wasn’t right, and they both agreed it wouldn’t be best to move forward.

The relationship between Nick Cannon and Selita Ebanks was also short-lived, so much so that most of us forgot it even existed. Nevertheless, comedian and sometimes actor, Cannon met superstar model and future muse of Kanye West in 2007, and he was beyond smitten. He made an attempted rush to the finish line when he proposed to her via jumbotron in the middle of Time Square. But five short months later, Selita called it quits, and now the relationship is nothing but a distant memory for her, and we assume Cannon, too. There’s little comparison after marrying (and divorcing) Mariah Carey, right?

It was the beginning of the ‘90s when Kiefer Sutherland and Julia Roberts met on the set of Flatliners and began a romantic relationship that grabbed everyone's attention. The couple got engaged fast and began planning a modest 150-guest affair, but like her character in Runaway Bride, Roberts began to get cold feet just days before the wedding. In fact, she called it off in 1991, only two days before they planned to seal the deal. Kiefer spoke up about the planned nuptials in a 2016 interview and praised Roberts for being brave enough to know they were making a mistake and boldly calling it off.

Naya Rivera and Big Sean’s relationship was short, sometimes sweet, and really dramatic. The pair got together in April 2013, were engaged by October 2013, and broke up in April 2014. In her memoir, Sorry Not Sorry, Rivera wrote that she found out about the end of her engagement on the internet. Prior to that, the couple had been fighting for several days while Big Sean was traveling, and when he wouldn’t agree to see her after he returned, Rivera showed up at his house only to find Ariana Grande sitting crossed-legged on his couch.

When Rivera passed away in 2020, Big Sean penned an emotional tribute to her on Instagram: "I appreciate and cherish everything that ever happened between us for making me wiser and a better person. I’m still grieving and in shock, I can’t believe this is real."

After a tumultuous relationship with Jesse James, Kat Von D moved on with Joel Zimmerman, more professionally known as Deadmau5. The former couple met in September 2012, and in December of that same year, Deadmau5 proposed to Kat Von D over Twitter, and she happily accepted. By June of 2013, the couple had separated with Kat Von D citing allegations of cheating as the means to their end. Zimmerman has denied the rumours, claiming – just as Ross did with Rachel – that he and Kat were most definitely on a break.

Before filming with Jennifer Aniston on the set of Friends, Tate Donovan fell hard and fast for America’s sweetheart after being introduced by mutual friends. Donovan claims he wasn’t even aware of who she was at the time, because he had yet to see the hit television show she was made famous for. And, to make matters even more interesting, the celebs dated for almost three years and were engaged by 1998, two years before actually appearing together on a six-episode run on Friends. Sadly, they were facing a breakup at the time of filming, and Donovan has spoken openly about just how painful that was for them both.

Before she made Tom Cruise jump up and down on Oprah’s couch like a maniac, Dawson’s Creek alum, Katie Holmes was engaged to American Pie star, Chris Klein. Holmes' first boyfriend that grabbed the media's attention was fellow creeker, Joshua Jackson, but when that fizzled, she moved on to Klein. The couple met in 2000, were engaged by 2003 and broke things off in 2005. Despite that, it’s rumoured and that Holmes and Klein have remained friendly with each other ever since. Some tabloids even began to speculate that Holmes was leaning on Klein after her departure from the arms of Jamie Foxx, but it wasn't confirmed and she's now dating Emilio Vitolo Jr.

She famously dated her partner in crime on The O.C. for three years, but when things went south with co-star Adam Brody, Bilson moved on to Hayden Christensen. This famous couple dated on-and-off for ten years, and were engaged for nearly half of that. Bilson gave birth to their daughter Briar Rose in 2014, and less than three years later, they decided to call it quits again, but this time the breakup stuck. The rumour mill has contributed their relationship woes to Christensen’s need to remain private and Bilson’s desire to stay in the limelight, but only the two of them will truly know why it ended.

Paris squared is composed of socialite and former reality star, Paris Hilton and Greek shipping heir Paris Latsis. The couple came together in 2004 and were engaged months later. Fans of Hilton rejoiced in the news of her impending nuptials, but their excitement came to a grinding halt just shy of a year later in 2005 when the two rich kids decided to part ways. Not one to dwell on a failed relationship, Hilton went on to date another Greek heir, Stavros Niarchos, followed by Good Charlotte guitarist Benji Madden, The Hills actor Doug Reinhardt, Las Vegas nightclub owner Cy Waits, Spanish model River Viiperi, and businessman Thomas Gross. She was later engaged to actor Chris Zylka but called off their engagement in 2018. In 2021, Hilton married Carter Reum.

Before dating Amber Rose and marrying Kim Kardashian, Kanye West was engaged to designer Alexis Phifer. The relationship started off slow in 2002 when the couple began dating on and off. West didn’t show up with the big proposal until 2006 when he popped the question over a lobster and pasta dinner during a vacation to Capri. But things took a turn by 2008 when the engagement was called off. Rumours spurred that Kim Kardashian provoked the breakup when she was seen with the couple at a party in 2007. West ended up marrying Kardashian in 2014, but the couple have since ended things and filed for divorce.

Another ‘90s power couple came in the form of Johnny Depp and Winona Ryder, who began their romance in 1989 when Ryder was only 17 years old, making Depp nine years her senior. The couple were engaged by 1990; the same year they starred together in Edward Scissorhands. After four years together, Ryder and Depp ended their engagement in 1993 due to their rising fame and acknowledgement that they were too young to take the plunge. Ryder spoke to Time magazine in 2016 when Depp was battling accusations of domestic violence by his estranged wife, Amber Heard. She claimed that while she can’t speak for Heard directly, she told the public that Depp was never once abusive towards her during their time together.

The Scandal actress dated Moscow for several years before becoming engaged. The couple had a pretty public split in 2007, which led to Washington to become more private about her personal life. Since the breakup, both stars have moved on, with Washington secretly marrying Nnamdi Asomugha in 2013.

Jennifer Lopez called off her two-year engagement to baseball star Alex Rodriguez and wasted no time getting back together with Ben Affleck shortly after the split. There were rumours that A-Rod had cheated with Southern Charm star Madison LeCroy. After denying the rumours and sticking together amid the drama, JLo finally pulled the plug on the relationship in April of 2021.