By Jessica Wedemeyer
4:00am PDT, Aug 23, 2022
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Can you remember who Jessica Alba almost married? Or who came close to exchanging vows with Brad Pitt? Keep reading to take a look back at 45 Hollywood couples who called off their engagements, starting with this pair… There once was a time when "The O.C." star Tate Donovan was romantically linked to some of Hollywood's most talented (and beautiful) women. Sandra Bullock romanced the actor after they met filming "Love Potion No. 9" in 1990, later admitting to Vanity Fair that she "chased [Tate] like a dog." Pal George Clooney helped get them together by encouraging Tate to spend time with Sandra. They were a couple until 1995 and were even briefly engaged during that time. Tate was in another high-profile-relationship-turned-engagement…
Keep reading for more, and to see more stars who ended engagements…
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In 1995 — the same year Tate Donovan and Sandra Bullock called it quits — the "Hercules" voice actor met "Friends" star Jennifer Aniston through mutual pals. Despite breaking up after a month of dating, they got back together three weeks later and went on to get engaged in 1998, though it was brief — they'd already ended their romance by the time they played love interests on her show "Friends" that same year. Jen and Sandra Bullock have since spoken about their shared ex. "We were introduced by our former boyfriend. I say 'our' because you and I both partook of this one human being," said Sandra, who interviewed Jen for Interview magazine. "We both partook of Tate… Who was a very patient human being, given that he dated us both." Tate has a thing for women who are "talented, funny, kind, introspective and generous," joked the "Bird Box" actress. And, Jennifer added, "lovers of architecture" and "lovers of interior design."
RELATED: Celeb couples' red carpet debuts
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Long before she starred in "Runaway Bride," Julia Roberts was one herself! America's Sweetheart practically left "Flatliners" co-star — and love of more than a year — Kiefer Sutherland at the altar when she backed out of their June 1991 nuptials just days before they were scheduled to tie the knot. To add insult to injury, she flew away to Dublin with actor Jason Patric — Kiefer's "Lost Boys" co-star and friend — the same day she was supposed to say "I do." Nearly 30 years later, Kiefer and Jason appeared on an April 2021 episode of the "Inside of You with Michael Rosenbaum" podcast and for the first time, together talked about how they reconciled their friendship after nearly 20 years of estrangement. "That was a difficult time for me, and I think it was an uncomfortable time for both of them," Kiefer said. "The truth where I'm coming from: You fall in love, you fall in love. There's nothing you can do about that. [Julia's] an extraordinary person, and he is too. Timing is what it is, and everyone moves on from that." The men had buried the hatchet by they time they co-starred in a 2011 Broadway revival of "That Championship Season." "When I saw him again, there were a few words and more of a laugh and a toast," Jason shared. "I've said before that [he and Julia] have both been subsequently married since a couple times, and I think they're both very happy in their lives. What lasted after all that was me and Kiefer as 35-year buddies."
RELATED: Stars who got married in Las Vegas
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Brad Pitt asked girlfriend of two years Gwyneth Paltrow, who was also his co-star in "Seven," to be his wife while she was visiting him on the Mendoza, Argentina, set of "Seven Years in Tibet" on Dec. 19, 1996. But it wasn't meant to be: They called it quits just six months later.
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Johnny Depp sure loves being in love! The Oscar nominee was married to makeup artist Lori Allison from 1983 to 1985 and shared a 14-year partnership with Vanessa Paradis from 1998 to 2012. He's also been engaged three times: to actresses Sherilyn Fenn, Jennifer Grey and Winona Ryder. Johnny reportedly asked the "Heathers" star to be his wife just five months after they met at a premiere. To commemorate their love, Johnny tattooed "Winona Forever" on his right bicep — but not everything is as permanent as a tattoo. After a three-year engagement, Winona and Johnny parted ways. He later changed the inking to read "Wino Forever."
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Jennifer Lopez and Ben Affleck — who were know by the portmanteau "Bennifer" during their intense romance in the early aughts — got engaged in November 2002 after less than a year of dating when Ben presented his "Gigli" co-star with a 6.1-carat pink diamond ring from Harry Winston. But the duo called it off in September 2003 just four days before the scheduled date of their $2 million wedding — and split for good — or so we thought — a few months later. Nearly 20 years later, J.Lo called off another high-profile engagement…
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In April 2021 — a month after denying reports they'd split after four years together — Jennifer Lopez and Alex Rodriguez announced that they'd ended their engagement as they'd "realized we are better as friends." The news came two years after he proposed on bended knee with an enormous emerald-cut diamond ring on a Bahamian beach in March 2019.
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Olivia Wilde and Jason Sudeikis met at a "Saturday Night Live" wrap party in 2011 and began dating six months later. The actress-director and the "Ted Lasso" star got engaged in 2013 and had two kids together, but never tied the knot. They ultimately ended their nine-year romance in 2020.
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Back in the early 2000s, Alanis Morissette and Ryan Reynolds were head-over-heels in love. The pair began dating in 2002 and got engaged in 2004. "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," Alanis said a year after their engagement. They called it off in 2007, inspiring Alanis's hit album "Flavors of Entanglement." She now shares three kids with rapper Souleye while Ryan has three daughters with second wife Blake Lively, whom he wed after divorcing Scarlett Johansson.
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Once upon a time, Jennifer Morrison was set to wed "House" co-star Jesse Spencer, whom she met while shooting the drama's pilot episode in 2004. He popped the question in French at the Eiffel Tower while vacationing in Paris over the holidays in 2006. Jennifer had already picked out an Elie Saab wedding gown when they called off their nuptials in August 2007.
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Once upon a time, Linda Evangelista and "Sex and the City" star Kyle MacLachlan were happily in love. The couple met on the set of a photoshoot in 1992 and were inseparable for six years, during which they got engaged. The romance wasn't meant to be, however, and the pair split. "I didn't really want to get married as I couldn't see the point and the relationship wasn't really going anywhere," Kyle told the Evening Standard.
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What's worse than your fiancé leaving you? Your fiancé leaving you and marrying someone else without your knowledge! Way back when, Laura Dern was engaged to Billy Bob Thornton, whom she met while guest-starring on an episode of "Ellen" in 1997. They announced their engagement in 1998 but their love story was cut short in 2000 when Billy married his "Pushing Tin" costar Angelina Jolie while Laura was out of town filming a movie. The "Big Little Lies" actress never heard from him again. "It was like a sudden death. For no one has there been closure or clarity," Laura told Talk magazine.
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Before Gigi Hadid, Zayn Malik romanced a fellow "The X Factor" alum, Perrie Edwards, from 2012 to 2015. They announced their engagement in August 2013 — but they called it quits shortly after that. According to the Little Mix singer, Zayn dumped her via text.
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Before Kanye West married and divorced Kim Kardashian, he was engaged to an entirely different woman! The rapper began dating designer Alexis Pfeiffer in 2002 and they were engaged four years later. They parted ways in 2008 and the rest, as they say, is "Keeping Up With the Kardashians" history.
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Mary-Louise Parker and Jeffrey Dean Morgan are just friends today, but once upon a time, they were planning to wed. They dated on and off after meeting on the set of "Weeds." Jeffrey popped the question in February 2008 but by April, they'd split for good.
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Back in the 1980s, Demi Moore and Emilio Estevez were a Hollywood "it" couple. The "St. Elmo's Fire" co-stars got engaged in 1985 but called off their December 1986 nuptials. Demi went on to marry (now ex-husbands) Bruce Willis and Ashton Kutcher while Emilio was briefly married to pop singer Paula Abdul.
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Robin Wright found love again with Ben Foster after her divorce from Sean Penn in 2010. The couple got engaged in early 2014 but called it off that November. Robin and Ben reconciled in January 2015 but the engagement was called off for good the following August. Ben now shares a daughter with wife Laura Prepon, whom he wed in 2018, while Robin secretly wed Clement Giraudet the same year.
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Chris Klein asked Katie Holmes to be his wife in late 2003 after a three-year courtship. Just a month after they called off their two-year engagement, Katie went on her first date with Tom Cruise, her future ex-husband.
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Before she found love with current hubby Nnamdi Asomugha, Kerry Washington was in a long-term relationship with actor David Moscow. He popped the question in 2004 but the two called it quits in 2007. The public nature of their failed relationship inspired Kerry to be more private about her marriage to Nnamdi.
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Britney Spears knows a thing or two about mixing business with pleasure! The pop star's former agent and boyfriend of two-and-a-half years, Jason Trawick, popped the question with a Neil Lane sparkler on his 4th birthday in December 2011. But they never made it to the altar. The duo called it quits in January 2013 after a year-long engagement.
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When she was just 19, budding starlet Jessica Alba accepted a marriage proposal from her 32-year-old "Dark Angel" co-star Michael Weatherly after just a few months of dating. They ended their two-year engagement in August 2003.
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Sean Penn and Charlize Theron took their longtime friendship to the next level in December 2013 and reportedly got engaged less than a year later. But the duo parted ways in 2015 when the South African stunner reportedly began "ghosting" her love of a year and a half by ignoring his calls and texts. In 2020, Charlize dismissed reports they were engaged, saying it's "not true" that she "almost married Sean."
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Hayden Christensen and Rachel Bilson's love story began in 2007 when they met while filming the sci-fi flick "Jumper." They announced their engagement in 2008 but called it off due to distance in 2010 (at the time, Rachel was in Los Angeles while Hayden spent the majority of his time in Vancouver). Three months later, the "Star Wars" actor and "The O.C." star rekindled their relationship. They went on to welcome daughter Briar Rose in 2014, but they weren't a happy family for long — Hayden and Rachel went their separate ways for good in 2017 after nearly 10 years of coupledom.
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Nick Cannon asked Selita Ebanks to be his wife in May 2007 after just months of dating. The multi-hyphenate popped the question on a Jumbotron in New York City's Times Square and presented the model with a 12-carat diamond ring following the annual Met Gala. Selita said yes — but five months later, they were over.
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In September 2005, Lance Armstrong traded in his bicycle wheels for a set of oars and rowed girlfriend of two years Sheryl Crow into the middle of a lake in the mountains. There, he asked her to be his wife with a 6-carat cushion-cut platinum-set diamond. They called off their engagement five months later.
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The ink was barely dry on Jesse James and Sandra Bullock's divorce papers when he started romancing celebrity tattoo artist Kat Von D in August 2010. They became engaged in January 2011, briefly split in July 2011, reconciled in August 2011 and finally called it quits for good the following month. Kat later claimed that he'd cheated on her with 19 women.
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Big Sean and the late Naya Rivera shocked fans when they got engaged in October 2013 after only a few months of dating. The flames soon fizzled and the pair called off their wedding in April 2014. Naya went on to marry former boyfriend Ryan Dorsey, whom she later divorced, on the same date she planned to marry Sean, while Sean reportedly penned his hit song "I Don't F*** With You" about his ex-fiancée.
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In May 2005, Greek shipping heir Paris Latsis asked childhood pal and girlfriend of five months Paris Hilton to be his wife with a 23-carat diamond sparkler. They called off their engagement after just four months and days later, the heiress moved on with Stavros Niarchos. But that wasn't her only called-off engagement…
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Paris Hilton and Chris Zylka seemed destined for happily ever after after their romance got serious quickly. The couple got engaged over the New Year holiday in 2017 but had called off their wedding by the fall of 2018. The biggest point of contention, though, was whether Paris could keep her 20-carat ring … which ultimately, she was able to do. On to the next!
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Wrestlers John Cena and Nikki Bella seemed like a match made in WWE heaven when they started dating in 2012. Fans were shocked and delighted when John proposed to his longtime love after their mixed tag-team match at WrestleMania 33 in 2017, but it didn't last. Nikki called off their wedding and broke up with John in April 2018 just weeks before they were set to say "I do" in Mexico. They tried to work it out over the next few months but split for good in July.
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Heather Locklear must have been homesick for "Melrose Place" when she reconnected with former co-star Jack Wagner in early 2007. Four years later, she accepted his marriage proposal, but the stars who played Amanda Woodward and Peter Burns called off their engagement in November 2011.
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After less than a year of togetherness, Jude Law asked Sienna Miller to be his wife on Christmas Day 2004 with a $35,000 gold band featuring nine diamonds. Their relationship turned rocky when Jude's affair with his kids' nanny, Daisy Wright, became public knowledge in July 2005. The "Alfie" co-stars were off and on for more than a year after the cheating revelation but officially called off their engagement in November 2006. They reconciled from December 2009 to February 2011, but it just wasn't meant to be!
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Sienna Miller and Tom Sturridge parted ways in July 2015 after four years of togetherness. The couple reportedly became engaged in early 2012, just a few months before they welcomed daughter Marlowe in July 2012.
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Broadway stars Anthony Ramos and Jasmine Cephas Jones seemed to be a match made in "Hamilton" heaven — they met in 2015 during rehearsals for the hit Broadway musical, started dating and announced their engagement in 2019 — but their once loving relationship eventually found itself on the rocks. They called it quits in 2021 after a viral TikTok video alleged the "In the Heights" star cheated on the Emmy-winning actress.
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Maksim Chmerkovskiy and Karina Smirnoff took their friendship of more than 14 years to the next level in September 2008. He popped the question three months later while they were celebrating New Year's Eve in Las Vegas. By September 2009, the "Dancing With the Stars" pros had called it quits, reportedly due to their differing views on parenthood.
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Taraji P. Henson began dating former NFL player Kelvin Hayden in 2016 and they got engaged in May 2018. Unfortunately, their union wasn't meant for forever — they broke up in 2020. While visiting The Breakfast Club, the "Empire" star revealed she was willing to do couples therapy to repair their relationship. "I was like, 'Therapy. Let's do the therapy thing.' But if you're both not on the same page with that, then you feel like you're taking it on yourself," she said.
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Courteney Cox and Snow Patrol guitarist Johnny McDaid got engaged in June 2014 after only six months of dating. He moved into Courteney's Malibu home, but it wasn't smooth sailing. According to TMZ, the Irish musician moved out before Thanksgiving after realizing they wanted to lead different lifestyles. All wasn't lost, however, and the couple rekindled their romance in early 2016, though they didn't get engaged again. "He's not my fiancé," Courteney explained during a 2019 appearance on "The Ellen DeGeneres Show." "We were engaged to be married but now we're just together."
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Liam Hemsworth and Miley Cyrus got engaged in May 2012 when they "Hunger Games" hunk popped the question with a 3.5-carat cushion-cut Neil Lane sparkler, which his fiancée only occasionally wore during their engagement. By September 2013, the "Last Song" co-stars were kaput. They rekindled their romance in 2016 and got married in December 2018, only to divorce less than eight months later.
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Emma Roberts and Evan Peters were first linked in July 2012 after they worked together on the indie film "Adult World." The "American Horror Story" co-stars became engaged in December 2013 — just a few months after Emma was arrested on domestic violence charges following a heated argument with Evan in their Montreal hotel room. They called off their engagement in June 2015 but rekindled their romance in September 2016… only to call things off again in 2019.
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When Lady Gaga attended the Grammys in February 2019 without her giant pink gemstone engagement ring — and minus fiancé Christian Carino — speculation that the singer-actress and her agent had called it quits emerged. Later that month, People magazine confirmed that the pair, who started dating in early 2017, had indeed ended their romance and their engagement. "It just didn't work out. Relationships sometimes end. There's no long dramatic story," an insider told People. This wasn't Lady Gaga's first broken engagement, however…
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Lady Gaga and Taylor Kinney were together for five years — and engaged for more than a year — before they finally parted ways. The "Chicago Fire" actor proposed to Gaga with a heart-shaped diamond on Valentine's Day 2015. Fans finally got some insight into the split when her documentary, "Gaga: Five Foot Two," aired as the pop star explained, "My love life has just imploded. I sold 10 million [records] and lost Matt. I sold 30 million and lost Luke. I did a movie and lose Taylor. It's like a turnover. This is the third time I've had my heart broken like this."
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In January 2019, news emerged that "Captain Marvel" star Brie Larson and Phantom Planet frontman Alex Greenwald had called off their engagement of nearly three years. "They have taken a step back from their engagement for the time being but they remain close," a source told People magazine of the pair, who started dating around 2013.
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Blink and you missed it! Pop star Ariana Grande and "Saturday Night Live" comedian Pete Davidson had been dating for a month when they got engaged in June 2018. However, by October, the couple had called it quits.
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Rob Kardashian and Blac Chyna were first linked in January 2016. After just 10 weeks of dating, they got engaged and a month after that, they revealed Chyna was pregnant. Daughter Dream arrived later that year but the reality TV stars' messy and contentious relationship didn't last: They ended their engagement in February 2018.
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Mariah Carey found love with billionaire James Packer in 2014. In 2016, he proposed with a 35-carat diamond ring and Mariah said yes. However, it wasn't meant to be. Following a dramatic split in October 2016, Mariah reportedly demanded that James pay her a settlement to walk away since she made sacrifices to be with him. As the story goes, Mariah got to keep her bling once the dust settled!
