Celebrity Engagements That Were Called Off Before the Altar – SheKnows

Jennifer Lopez & Ben Affleck

While they ended up walking down the aisle eventually, Jennifer Lopez and Ben Affleck first called it quits back in 2004 when they were engaged to be married. The couple, who met on the set of Gigli, got engaged in Nov. 2002.

Many years after their split, in 2022, they finally went down the aisle and said their “I do’s.”

Jude Law & Sienna Miller

In one of the most notorious affairs in celebrity history, Jude Law and Sienna Miller called off their engagement in July 2005 after the actor admitted to an affair with their his children’s nanny, per Brides.

The pair, who had gotten engaged in late 2004, eventually got back together in 2009 before called it quits for the second time in 2011. 

Pete Davidson & Ariana Grande

Pete Davidson and Ariana Grande went full steam ahead in their whirlwind relationship. The pair, who started dating in May 2018, got engaged just weeks into their relationship in June. Sadly for fans of the couple, however, the two called off their engagement in October, per People.

Demi Moore & Emilio Estevez

After meeting in St. Elmo’s Fire, co-stars Demi Moore and Emilio Estevez started dating and eventually got engaged in 1985. Per Brides, the two then had an on-again, off-again relationship and even set a date for the wedding but eventually called it quits in 1987.

Johnny Depp & Jennifer Grey

In another blast-from-the-past relationship, Johnny Depp and Jennifer Grey moved quite quick during their brief relationship. The pair got engaged in 1989 and broke up about a year later, per Brides. 

Johnny Depp & Winona Ryder

Depp shared a similar story in his relationship with Winona Ryder. According to Us Weekly, Depp and Ryder got engaged in 1990 after dating for just five months. The two eventually split in 1993 before ever making it down the aisle. 

Kiefer Sutherland & Julia Roberts

Remember this duo? In case you didn’t even know these two dated, Kiefer Sutherland and Julia Roberts got engaged back in 1990 after dating for a year. According to People, their wedding date and location (20th Century Fox’s Soundstage 14) was even set but Roberts got cold feet and broke things off three days before she walked down the aisle. Talk about a runaway bride!

Brad Pitt & Gwyneth Paltrow

In the beginning of their careers, Brad Pitt and Gwyneth Paltrow found each other and fell in love. The pair, who just happened to have the exact same hairstyle in this picture, started dating in 1994 and got engaged two and a half years later. In 1997, however, the two called it quits. 

Tate Donovan & Jennifer Aniston

Jennifer Aniston, who went on to marry Pitt shortly after, also lived a short engagement story of her own. Aniston and her Friends co-star Tate Donovan were together for three years before calling of their engagement in 1998, per Us Weekly. 

Sandra Bullock & Tate Donovan

Speaking of Donovan, the actor almost said “I do” to another A-lister: Sandra Bullock. The pair, who met on the set for Love Potion No. 9, also got engaged but broke things off three years into their relationship in 1995, per OK!

Alanis Morissette & Ryan Reynolds

Long before Blake Lively was in the picture, Ryan Reynolds and singer Alanis Morissette had a relationship that almost led to marriage. According to Us Weekly, the pair, who started dating in 2002, announced they were engaged in 2004. Three years into their engagement, however, they called it quits in 2007. 

Sean Penn & Charlize Theron

Hollywood power couple Sean Penn and Charlize Theron seemed to be going strong in their relationship when they announced their engagement in 2014, Us Weekly reports. A year later, however, the two went their separate ways. 

Hayden Christensen & Rachel Bilson

Hayden Christensen and ex Rachel Bilson lived quite a few up and down years together. The pair, who first met on the set of Jumper, got engaged in 2008 before calling it off less than two years later in 2010. Shortly after, however, the two got back together and in 2014, welcomed daughter Briar Rose Christiansen. In 2017, they former couple called it quits yet again.

Lenny Kravitz & Nicole Kidman

Back in 2003, unexpected couple Lenny Kravitz and Nicole Kidman got engaged, per Us Weekly. Soon after, however, the two called it quits but remained on shockingly good terms. 

“I knew Zoë because I was engaged to her father,” Kidman revealed back in 2017, per Time. “It’s all in the family! I love Lenny; he’s a great guy,”

Katie Holmes & Chris Klein

Prior to tying the knot with Tom Cruise, Katie Holmes almost walked down the aisle to fellow actor Chris Klein. Per Us Weekly, the pair dated from 2000 to 2005 and got engaged three years into their relationship in 2003. Shortly after their split, however, Holmes had already moved on with Cruise. 

Lance Armstrong & Sheryl Crow

In another unexpected duo in this list, Sheryl Crow and former cyclist Lance Armstrong almost said their “I do’s.” The pair, who started dating in 2003, announced their engagement in 2005. Less than a year later, however, the two went their separate ways. 

Jennifer Morrison & Jesse Spencer

While their characters in House eventually got married, Jennifer Morrison and Jesse Spencer never walked down the aisle in real life. The pair, who announced their split in 2007, continued to work together for five years as exes and onscreen love interests. 

“We are still very close, and we look forward to continuing to work together on House,” they told People in a joint statement at the time, per Entertainment Tonight. 

Mary Louise Parker & Jeffrey Dean Morgan

After meeting on the set of Weeds in 2006, actors Mary Louise Parker and Jeffrey Dean Morgan began dating, per Brides. Two years later, in Feb. 2008, the two announced their engagement but less than two months later, the pair called it quits. 

Jason Trawick & Britney Spears

After being engaged for over a year, Britney Spears and agent Jason Trawick called it quits in 2012. “I’ll always adore him and we will remain great friends,” Spears told Us Weekly in a statement at the time. “As this chapter ends for us a new one begins.”

Big Sean & Naya Rivera

Less than six months after announcing their engagement, Big Sean and the late Naya Rivera called it quits in 2014. “After careful thought and much consideration, Sean has made the difficult decision to call the wedding off,” his rep told Us Weekly at the time. “Sean wishes Naya nothing but the best and it is still his hope that they can continue to work through their issues privately. We will not be commenting again on this matter.”

Nikki Bella & John Cena

In one of the most documented called-off-engagements in celebrity history, Nikki Bella and John Cena decided to break up just days before their wedding in April 2018, per Us Weekly. The pair then reconciled a month later before calling it quits a second time in July. 

Maggie Q & Dylan McDermott

After meeting on the set of The Stalker, co-stars Maggie Q and Dylan McDermott started dating. A year later, in 2015, they announced their engagement. Four years later and still no wedding, however, they announced their split, per Us Weekly. 

Shailene Woodley & Aaron Rodgers

In one of the most recent examples of called-off engagements, Shailene Woodley and Aaron Rodgers ended their engagement in Feb. 2022, per Us Weekly. The pair, who had been dating since 2020, announced their engagement a year earlier in Feb. 2021.