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Hollywood’s Broken Engagements: Stars That Didn't Make It Down the Aisle

If it’s meant to be, it’ll be. Hollywood has produced many goal-worthy romances through the years, including Chrissy Teigen and John Legend as well as John Krasinski and Emily Blunt, but not all celebrity couples have been as lucky to make their way to the altar.

John Cena and Nikki Bella became WWE’s “It Couple” after going public with their romance in 2012. The twosome got engaged in 2017, but they exclusively confirmed their split to Us Weekly in April 2018. While they reconciled shortly after, Cena and Bella broke up for good that July.

The one thing I really regret about showcasing the breakup [on my show Total Bellas] is that no one got to hear [John’s] voice, and it just seemed so one-sided,” she told Health magazine in its January/February 2020 issue. “I felt like that wasn’t fair to him because he was on this journey with us from the beginning. What people don’t realize is that John never took one paycheck from Total Bellas. It was beautiful — he was fully there to support me.”

It all worked out in the end for the former flames. In October 2020, the Blockers actor quietly wed girlfriend Shay Shariatzadeh. Meanwhile, Bella got engaged to Dancing With the Stars pro Artem Chigvintsev in November 2019, and they welcomed their son, Buddy, in July 2020.

Ariana Grande and Pete Davidson, for their part, began dating in May 2018 after ending their long-term relationships with Mac Miller and Cazzie David, respectively. They got engaged that June, only to call it quits four months later.

In Vogue’s August 2019 cover story, the “Positions” singer called her relationship with the Saturday Night Live star “an amazing distraction,” adding: “It was frivolous and fun and insane and highly unrealistic, and I loved him, and I didn’t know him.”

Davidson has since been linked to Kate Beckinsale, Margaret Qualley and Kaia Gerber. As for Grande, she was briefly linked to Social House singer Mikey Foster before finding love with Los Angeles real estate agent Dalton Gomez in mid-2020.

Unlike Cena and Bella as well as Grande and Davidson, Kristin Cavallari and Jay Cutler did make it down the aisle despite initially calling off their three-month engagement in 2011. After tying the knot in 2013 and becoming parents to three children, they revealed their separation in April 2020.

Though their divorce battle got off to a rough start, the Very Cavallari alums have worked to establish a good coparenting relationship. “There’s good days and bad days, but I’m feeling really good right now,” the Uncommon James founder told Us in October 2020. “I’m feeling really happy and really free and that’s a nice feeling.”

Scroll down to see which celebrity couples have called off their engagements.


Gabby Windey and Erich Schwer
Windey and Schwer got engaged on season 19 of The Bachelorette. One month after the season finale premiered, Windey was seen not sporting her engagement ring, fueling rumors that the two called things off. While competing on Dancing With the Stars in November 2022, the former cheerleader confirmed the breakup. “Ultimately, I'm just grateful that I was able to do it on my own terms and when I was ready,” she said to Us after the episode aired. “It was just a new experience overall — being so public and being thrown into this. I think now it's just kind of trying to move forward.” Craig Sjodin/ABC via Getty Images
Leah Messer and Jaylan Mobley
The MTV personality and the cyber security officer announced they were parting ways in October 2022, two months after they had gotten engaged. “While the last year has been tremendously exciting for both of us, we’ve realized that it’s best we walk separate paths,” the former couple said in a statement to Us at the time. “We are so grateful for the lessons, growth, and memories we’ve had in this relationship.” Courtesy of Leah Messer/Instagram
Michelle Young and Nayte Olukoya
The couple got engaged on season 18 of The Bachelorette and six months after their proposal episode aired, the twosome announced they had split. “To those who have supported Nayte and I, including Bachelor Nation, I know I speak for both of us when I say having a relationship in the public eye has not been easy,” the Minnesota native said in June 2022. “I’m struggling to say Nayte and I will be going our separate ways but I stand with him in knowing the heaviness that is present in both our hearts as this relationship has been very real for both of us.” ABC/Craig Sjodin
Bella Thorne and Benjamin Mascolo
The former Disney star and the Italian singer got engaged in March 2021 after dating for two years. In June 2022, the pair called off their engagement and split. “I wish only the best for this person and I will always be there for her. I love you,” Mascolo wrote via Instagram at the time. Maria Laura Antonelli/Shutterstock
Amber Riley and Desean Black
The Glee alum and her fiancé called it quits in March 2022 after they were engaged for more than a year. "I wish him the best," Riley said while appearing on the "Nice & Neat" podcast at the time. "I don't have anything horrible or bad to say." Shutterstock; Inset: Courtesy of Desean Black/Instagram
Sarah Chalke and Jamie Afifi
In September 2022, Us Weekly confirmed that the Scrubs alum and her fiancé had parted ways after being engaged for more than 15 years. The pair share two children, son Charlie and daughter Frankie. MB Pictures/Shutterstock
Demi Moore and Emilio Estevez
The St. Elmo’s Fire costars got engaged in 1985 after dating on and off for roughly two years. They set their wedding date for 1986 but ultimately called it quits in 1987 — the same year she married now-ex-husband Bruce Willis, with whom she shares three daughters: Rumor, Scout and Tallulah. Cannon/Kobal/Shutterstock
Sandra Bullock and Tate Donovan
Bullock and Donovan began dating and got engaged after filming their 1992 movie, Love Potion No. 9. They split in 1994. Bei/Shutterstock
Johnny Depp and Winona Ryder
After meeting in 1990, the former pair dated for five months before getting engaged. Depp even marked his love for Ryder with a tattoo that read, “Winona Forever,” but they split in 1993. Bei/Shutterstock
Jennifer Aniston and Tate Donovan
In addition to Bullock, Aniston is another former costar that Donovan has gotten engaged to. The now-exes, who appeared on her show Friends in the late 1990s, were together for three years before splitting in 1998. Berliner Studio/BEI/Shutterstock
Nicole Kidman and Lenny Kravitz
Us broke the news in October 2003 that the stars were planning to tie the knot. Years later, the actress would finally go public with the truth during an interview with The Edit. “Well, I knew Zoë [Kravitz] because I was engaged to her father,” she said of her Big Little Lies costar in February 2017. “It’s all in the family! I love Lenny; he’s a great guy.” Rick Diamond/Getty Images
Katie Holmes and Chris Klein
The cute couple were engaged in 2003 after three years together. Two years later, they broke off their engagement. Eight weeks later, she got engaged to now-ex husband, Tom Cruise. Getty Images
Jennifer Lopez and Ben Affleck
The twosome connected in 2002 while working on Gigli. Affleck popped the question later that year, but they never made it down the aisle. The wedding was set for September 2003 but was canceled just days before the nuptials due to “excessive media attention.” The actors officially called it quits in January 2004. Lopez went on to marry Marc Anthony in June 2004. The pair, who called it quits in 2011, share twins Max and Emme. The pair finalized their divorce in 2014. Affleck, for his part, moved on with Jennifer Garner in 2004, tying the knot in 2005. The duo split in 2015 after welcoming three children: Violet, Seraphina and Samuel. Their divorce was finalized in 2018. The “Jenny From the Block” singer and the Argo director rekindled their romance in May 2021, shortly after Lopez called off her engagement to Alex Rodriguez. In April 2022, Bennifer got engaged for a second time and eloped that following July. The pair had a second ceremony for their friends and family in August 2022. Matt Baron/BEI/Shutterstock
Sheryl Crow and Lance Armstrong
After three years together (six months of which they were engaged), the couple announced their split in February 2006. "We were up against her biological clock — that pressure is what cracked it," Armstrong later said. But Crow didn't need him: she adopted a son in 2007 and another in 2010. Getty Images
Sienna Miller and Jude Law
After the Alfie costars got engaged in 2004, Law publicly apologized for cheating on Miller with his children’s nanny. Though they ended their engagement in 2006, they reconciled in 2009 before splitting for good in 2011. Richard Young/Shutterstock
Gwyneth Paltrow and Brad Pitt
The couple met on the set of their movie Seven and seemed like the perfect Hollywood couple. But after nearly three years together (and a six-month engagement) they split in 2007. Paltrow later told Barbara Walters that she couldn't believe Pitt went out with her when she was "such a mess." Kevin Mazur Archive/WireImage
Alanis Morissette and Ryan Reynolds
The Canadian stars got engaged in 2004 after two years of dating, but their split was announced in February 2007. Reynolds went on to marry Blake Lively in 2012, while Morissette wed hip-hop artist Souleye in 2010. Matt Baron/BEI/Shutterstock
Jennifer Morrison and Jesse Spencer
The House costars called off their engagement with a joint statement on August 15, 2007, that said, "we are still very close, and we look forward to continuing to work together." Spencer, who proposed to Morrison over the holidays at the Eiffel Tower in Paris, had said it had taken him six months to ask Morrison to marry him. Getty Images
Selita Ebanks and Nick Cannon
Cannon popped the question to the Victoria's Secret model in the middle of NYC's Times Square in May 2007 — with the help of a jumbotron. Five months later, they split to focus on their careers. Getty Images
Kerry Washington and David Moscow
The Scandal star ended her engagement with the actor in 2007 after dating for four years. E. Charbonneau/WireImage.com
Jeffrey Dean Morgan and Mary-Louise Parker
Before secretly marrying Hilarie Burton in October 2019, the Walking Dead actor was gearing up to wed Parker more than a decade earlier. The former pair got engaged in February 2008, but they pumped the brakes on their romance that April. Gregory Pace/BEI/Shutterstock
Alexis Phifer and Kanye West
A source close to the couple — who split in April 2008 after they had been dating for six years — told Us that West "just couldn't keep it going — they are still friends and have broken up and gotten back together before, so it could work out." West had proposed to Phifer in 2006 while vacationing in Italy and had said he wanted to honor his late mother's wishes to make the relationship official. Getty Images
Nicollette Sheridan and Michael Bolton
The couple ended their relationship in August 2008 after a two-year engagement. The couple, who dated for five years beginning in 1992, had rekindled their romance after Sheridan's split from fiancé Nicklas Soderblom in 2005. Getty Images
Karina Smirnoff and Maksim Chmerkovskiy
After getting engaged on New Year's Eve in 2008, the Dancing With the Stars pros called it quits the next September. Getty Images
Jennifer Love Hewitt and Ross McCall
In January 2009, the Ghost Whisperer star pulled the plug on her wedding to the Scottish actor — even after she'd bought a wedding dress, and set a date and location for her spring 2009 destination wedding. "We are working it out," McCall said of their drama-filled engagement. "We are both still wearing our rings." Getty Images
Jason Wahler and Katja Decker Sadowski
Wahler called off his engagement in February 2009. "I have decided to end my engagement, and it's an amicable split," the former Hills star told Us at the time. "We agreed we are both just too young to be considering getting married right now." Getty Images
Melissa Rycroft and Jason Mesnick
The rose wasn't so sweet for Bachelor finalist Rycroft. In March 2009, Us reported that after the single dad gave the final rose — and the 3.1-carat Neil Lane ring — to the former Dallas Cowboys cheerleader in the finale, he shocked audiences by breaking things off six weeks later in a taped special. He decided to take another stab at his relationship with rejected finalist Molly Malaney. ABC/MATT KLITSCHER
Jake Pavelka and Vienna Girardi
After a televised romance and a six-month engagement, the two split in June 2010. The Bachelor Nation couple had been on the rocks for some time, fighting over everything from his lack of intimacy to her spoiled dog. Getty Images
Kristin Cavallari and Jay Cutler
After a three-month engagement in 2011, the Chicago Bears player changed his mind. Sources close to Cavallari told Us she was "blindsided" by Cutler, who later confirmed the split via Facebook. They later reconciled and got married in June 2013, but they announced their split in April 2020. They share sons Camden and Jaxon as well as a daughter named Saylor. Todd Williamson/Getty Images for JDRF
Brad Womack and Emily Maynard
The couple got engaged during The Bachelor's 15th season, but after postponing their wedding date, Maynard decided in May 2011 that Womack wasn't The One. Getty Images
Kat Von D and Jesse James
Breaking the news via Twitter in 2011, the L.A. Ink tattoo artist let the world know she and her fiance called it quits. "I am no longer with Jesse, and out of respect for him, his family and myself, thats all the info I'd like to share. Thanks for respecting that." Getty Images
Zoe Saldana and Keith Britton
The exes ended their 11-year relationship in November 2011. "For years he wasn't ready [for parenthood]. Then when he got ready, I didn't have time. I never held anything off because I was waiting for something to kick in. I don't think that far about tomorrow," she said during Lifetime's The Conversation With Amanda de Cadenet the following year. "I felt the urge to want to have a baby, and I wanted to, but I remember that respecting his decision — and making the decision to wait with him — was one of the most mature things." Saldana would go on to have three sons with Italian artist Marco Perego, whom she married in June 2013. Tony DiMaio/startraksphoto.com
Britney Spears and Jason Trawick
Engaged for more than a year, the pop star and the former CAA agent parted ways in January 2012. "I'll always adore him and we will remain great friends," Spears told Us in a statement. "As this chapter ends for us a new one begins," Trawick added. "I love and cherish her and her boys and we will be close forever." Getty Images
Hugh Hefner and Crystal Harris
Just five days before their wedding, the model decided not to walk down the aisle with the Playboy founder. “The wedding is off,” Hefner tweeted. “Crystal has had a change of heart.” The two reconciled and tied the knot in December 2012. They were married until the day Hefner died in September 2017. Getty Images
Miley Cyrus and Liam Hemsworth
After meeting on the set of their 2010 film, The Last Song, Cyrus and Hemsworth began dating before eventually getting engaged in 2012. They would eventually rekindle their romance in 2016 and got re-engaged that October. The duo revealed that they got married in December 2018, but they ultimately called it quits after less than eight months of marriage. Their divorce was finalized in January 2020. Matt Baron/Shutterstock
Naya Rivera and Big Sean
The Glee alum and rapper announced their split in April 2014 six months after getting engaged. "After careful thought and much consideration, Sean has made the difficult decision to call the wedding off," his rep told Us 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." Imeh Akpanudosen/Getty Images
Robin Wright and Ben Foster
Us exclusively confirmed in November 2014 that the pair called it quits. "She got swept up in the engagement last Christmas, but then their schedules got crazy and she realized it wasn't the right decision," an insider said. Their 14-year age difference didn't help matters either. Another source added: "The gap just ended up being too much. Ben was kind of immature. She couldn't deal with him anymore." He’d go on to marry Laura Prepon in June 2018. Araya Diaz/Getty Images
Sean Penn and Charlize Theron
The A-list movie stars began dating in December 2013 after Penn’s divorce from Robin Wright. Though they got engaged after a year together, they split in June 2015. Jordan Strauss/Invision/AP/Shutterstock
John Cena and Nikki Bella
The WWE stars exclusively confirmed to Us in April 2018 that they ended their six-year relationship just days before they were set to tie the knot. Us confirmed they reconciled one month later, but they called it quits for good in July 2018. Bella went on to get engaged in November 2019 to Artem Chigvintsev, with whom she welcomed a child in July 2020, while Cena married Shay Shariatzadeh in October 2020. Vince Flores/startraksphoto.com
Steven McQueen and Alexandra Silva
The Vampire Diaries alum exclusively revealed to Us in May 2018 that he and the model had split four months after he popped the question. “Actually, we called it off,” he said at the Voices In Displacement Gala. “But yeah, it’s just the way it was. It happened.” Joe Scarnici/Getty Images
Ariana Grande and Pete Davidson
The former duo’s whirlwind romance began in May 2018, and they got engaged the following month. They announced that October that they had parted ways. MediaPunch/Shutterstock
Michelle Williams and Chad Johnson
About nine months after getting engaged in March 2018, the Destiny's Child singer and her pastor fiancé split and called off their engagement. “I still remain fearless. I guess I still remain single! Things didn’t work out,” the musician wrote on her Instagram Story in December 2018. “The healing that needs to take place is a must! I don’t wanna destroy another relationship. Blessings to him, his family and ministry. #FEARLESS.” Noel Vasquez/Getty Images
Dylan McDermott and Maggie Q
The Stalker costars sparked dating rumors in 2014 and got engaged in 2015, but they ended their four-year engagement in 2019. Matt Baron/Shutterstock
Lamar Odom and Sabrina Parr
The personal trainer revealed in October 2020 that her engagement to the retired NBA player had ended. “Y’all know I’m honest and transparent so I have to be the first to let you guys know that I am no longer engaged to Lamar,” she wrote via Instagram. “This has been a difficult decision for me to make but it is the best for myself and my children.” Parr also noted that Odom “has some things that he alone has to work through.” MEGA
Demi Lovato and Max Ehrich
The Young and the Restless actor popped the question in July 2020, just four months after Us broke the news that they were an item. However, by September 2020, the pair had parted ways. Courtesy of Max Ehrich/Instagram
Liam Payne and Maya Henry
The former One Direction singer confirmed in January 2021 that he and Henry had broken off their engagement. The pair, who got engaged in August 2020, rekindled their romance in the summer of 2021. David Fisher/Shutterstock
Alex Rodriguez and Jennifer Lopez
One month after denying breakup rumors, the former couple announced their split in April 2021. “We have realized we are better as friends and look forward to remaining so,” the exes said in a statement to the Today show at the time. “We wish the best for each other and one another’s children. Out of respect for them, the only other comment we have to say is thank you to everyone who has sent kind words and support.” The former MLB player and the Hustlers actress started dating in 2017 and got engaged two years later. Matt Baron/Shutterstock
Clare Crawley and Dale Moss
The former Bachelorette ended her whirlwind romance with her season 16 suitor in January 2021, just two months after their proposal aired on TV. The pair briefly reconciled before splitting for good in September of that year. ABC/Craig Sjodin
Lala Kent and Randall Emmett
Us confirmed in November 2021 that the “Give Them Lala” podcast host and the Midnight in the Switchgrass director called off their three-year engagement. One month prior, Kent sparked split speculation when she wiped Emmett from her social media page following rumors that the filmmaker was spotted with two women at a hotel in Nashville. The estranged couple welcomed their daughter, Ocean, in March 2021. John Salangsang/Shutterstock
Raquel Leviss and James Kennedy
The Vanderpump Rules stars announced in December 2021 that they called off their engagement seven months after Kennedy proposed. The pair dated for five years before splitting. MediaPunch/Shutterstock
Shailene Woodley and Aaron Rodgers
Us confirmed in February 2021 that the pair were dating after first being linked in July 2020. The Green Bay Packers quarterback revealed he was engaged in February 2021 with Woodley confirming the news later that month. The romance, however, was short-lived with Us confirming in February 2022 that they’d split. Shutterstock (2)


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