Hollywood does a great job at setting unrealistic expectations for love, whether it’s rom-com meet-cutes that would never go down that way, or classic romances that have the happy endings we’ve learned not to expect in today’s day and age.
Of course, even Hollywood gets it right by getting love wrong, sometimes. Not all movies have a happily ever after ending, after all. And then it gets even realer — the real-life celebrity relationships that don’t end so great.
Some celebrity couples break up and then are required to continue working together (reason #1 why you shouldn’t date a coworker, no matter how strong your crush is). Some musically-inclined celebs go through a breakup and then write a song about it for the whole world to hear. And some celebrities get *this close* to tying the knot before they call the thing off — like these 24 failed celebrity engagements. Who gets to keep the ring?!
23. Julia Roberts and Kiefer Sutherland
How long they were together: 1 year
When they broke off the engagement: June 1991
Eight years before she starred as a woman known for leaving men at the altar in Runaway Bride, Julia Roberts did it in real life when she called off her wedding to Kiefer Sutherland a mere three days before it was supposed to take place — and immediately starting things up with Sutherland’s friend, actor Jason Patric. Sutherland was recently divorced from a three-year marriage to actress Camelia Kath, and he married now ex-wife Kelly Winn five years later, in a union that lasted eight years. Roberts managed to walk down the aisle a couple of years after splitting from Sutherland, marrying singer Lyle Lovett for two years. She’s currently married to her former cameraman Daniel Moder.
22. Miley Cyrus and Liam Hemsworth
How long they were together: Dated off and on for 2 years, 7 months; engaged for 1 year, 3 months (the first time around)
When they broke off the engagement: September 2013
Oh, the saga of Miley Cyrus and Liam Hemsworth. It seems like that crazy duo is off and on more than Ross and Rachel. Even their initial courtship, beginning with rumors in fall of 2009 and confirmed in spring of 2010, was on-again, off-again until the young lovers confirmed their engagement in summer of 2012 after months of rumors. The drama of their relationship continued until they ended the engagement after a little over a year. But never fear, the two kept putting fuel on the fire with rumors of a reconciliation over the years, which was eventually confirmed in fall of 2016. The pair is officially re-engaged. Will they end up officially tying the knot? Time will tell…
21. Gwyneth Paltrow and Brad Pitt
How long they were together: 3 years
When they broke off the engagement: June 1997
Gwyneth Paltrow was in her early 20s when she started dating Brad Pitt after starring as his wife in Se7en. She has since blamed the demise of their engagement entirely on herself — for being too young to know what she wanted, and for him being too good for her at the time. Both Paltrow and Pitt did get married: Paltrow married Coldplay frontman Chris Martin in 2002 and Pitt married actress Jennifer Aniston in 2000 and then actress Angelina Jolie in 2014. They also both got divorced: Paltrow and Martin split after ten years, Pitt and Aniston were married for five, and Pitt and Jolie made it two years before she filed for divorce. Paltrow is engaged again, to TV writer/director/producer Brad Falchuk. Who knows what’ll happen there.
20. Ryan Reynolds and Alanis Morissette
How long they were together: Dated for 1 year, 4 months; engaged for 2 years, 8 months
When they broke off the engagement: February 2007
Raise your hand if this was news to you! We all know that Alanis Morissette had a hot ‘n heavy relationship with Full House’s Dave Coulier (thanks to the iconic You Oughta Know), but we often forget that she was engaged to one of the most All-American actors around, Ryan Reynolds himself, in the mid 2000s. Overall, their relationship lasted four years, which may not be ’til death do us part but is more than a blip on the radar for such a seemingly mismatched couple. Both celebs are (seemingly) happily married now, Morissette to hip-hop artist Souleye since 2010 and Reynolds to actress Blake Lively since 2012 (after divorcing actress Scarlett Johansson in 2011 after three years of marriage).
19. Drew Barrymore and Leland Hayward
How long they were together: less than 1 year
When they broke off the engagement: 1991
Ready to get the heebie-jeebies? Drew Barrymore was only 16 when 24-year-old Leland Hayward proposed to her. That’s right; she was just a teenager, barely old enough to get a driver’s license. The engagement was, thankfully, short-lived. To her credit, Barrymore was mature for her age — she became emancipated from her mother at the age of 14 and grew up fast. Because one inappropriate proposal isn’t enough, Hayward was only the first during her teen years…
18. Drew Barrymore and Jamie Waters
How long they were together: 1 year, 8 months
When they broke off the engagement: November 1993
Still under 18 years old, Barrymore’s courtship and engagement to 24-year-old singer/actor Jamie Walters lasted longer than with Hayward (24 was apparently her favorite number as a teen). Although neither of her first two engagements was carried through, Barrymore tied the knot with her first husband at the tender age of 19, getting divorced a mere two months later. She was married to comedian Tom Green for a year in the early 2000s. In the mid-2010s, she was married to Will Kopelman. They had two children before divorcing after four years. Barrymore isn’t the only celebrity to have multiple broken engagements. Read on…
17. Kat von D and Jesse James
How long they were together: Dated for 7 months; engaged for 5 months
When they broke off the engagement: July 2011
Kat von D and Jesse James, friends for years, became romantically linked many years after von D’s divorce of three-year husband Oliver Peck but very shortly after James’s marriage to actress Sandra Bullock came crashing down following his infidelity (more on that later). Despite the tales of cheating, von D saw the best in him for long enough to date and get engaged… only to split when he cheated on her, too — with 19 women, a fact she publicized on Facebook. The next year, von D began the laser removal process to rid her arm of the tattoo of James as a kid.
16. Kat Von D and Deadmau5
How long they were together: Dated for 3 months; engaged for 6 months
When they broke off the engagement: June 2013
If you think it’s unreasonable to get engaged after just three months of dating (particularly when they broke up once during that period), just wait until you find out how Deadmau5 (born Joel Thomas Zimmerman) proposed: on Twitter, attaching a photo of the ring. Sure, we live in the digital age and all, but… really?! The ring wasn’t even finished. Deadmau5 clarified that he planned to swap the pictured diamond with a black one. It’s no shocker that the engagement didn’t last. Of course, the breakup was announced on social media, as well. Of course, two broken engagements isn’t the record in Hollywood. Why not go for three, like Johnny Depp?
15. Johnny Depp and Sherilyn Fenn
How long they were together: 3+ years
When they broke off the engagement: 1988
Sherilyn Fenn was the first of Johnny Depp’s three broken engagements, occurring AFTER his three-year marriage to Lori Anne Allison. Prior to her most famous role as Audrey Home in Twin Peaks, Fenn dated Depp in the mid to late ‘80s. She still posts throwback photos of them on social media (pictured above), referring to Depp as her first love. Fenn was married to Toulouse Holliday for three years and has been with Hollywood consultant Dylan Stewart since 2006.
14. Johnny Depp and Jennifer Grey
How long they were together: 1 year
When they broke off the engagement: 1989
Not long after not tying the knot with Fenn, Depp became engaged to Ferris Bueller’s Day Off and Dirty Dancing star Jennifer Grey. As evident by the low quality, candid airport photo of the two of them together, details of their relationship remained under wraps and very little is known about their brief courtship. Grey has been married to actor Clark Gregg of the Marvel universe since 2001, and the couple has one daughter.
13. Johnny Depp and Winona Ryder
How long they were together: 3 years
When they broke off the engagement: 1993
How could the romance in the tragically doomed Edward Scissorhands not be rooted in real life? Johnny and Winona were already dating when they starred in the movie together. Ryder was only a teenager when the couple got together, got engaged, and moved in together. After breaking up, Depp transformed his “Winona Forever” arm tattoo to “Wino Forever.” With one divorce and three broken engagements behind him, Depp didn’t get close to marriage again until his wedding to actress Amber Heard, whom he dated for four years before getting married. However, they divorced two years later with Amber alleging that Johnny was abusive. Ryder has been partnered with fashion design Scott Mackinlay Hahn since 2011.
12. Rob Kardashian and Blac Chyna
How long they were together: Dated for 3 months; 11 months
When they broke off the engagement: February 2017
Rob Kardashian and Blac Chyna had a whirlwind romance — the pair dated for just under three months before getting engaged, and Chyna announced her pregnancy just one month later. Breakup rumors swirled during the pregnancy when Kardashian went on odd social media cleanses and especially after Dream was born and Chyna was hacked, revealing private conversations that alluded to her cheating on Kardashian. Although the couple announced they were still together, less than four months later they called off the engagement. The drama has continued, with Kardashian sharing explicit photos of Chyna without her consent, and Chyna taking out a restraining order against Kardashian. Although they agreed to joint custody of their daughter last fall, Kardashian and Chyna are still embroiled in legal battles over various allegations against one another.
11. Sandra Bullock and Tate Donovan
How long they were together: 3 years
When they broke off the engagement: 1994
Years before her fame took off, Sandra Bullock starred alongside Tate Donovan in Love Potion No. 9 and the two started dating. They stayed together for three years, even getting engaged, before ending things. In subsequent interviews, Bullock always stood by her love for Donovan, even when he was linked with Jennifer Aniston shortly after that (see next). Perhaps it’s actually better that Bullock’s engagement fell through rather than ended in scandal and divorce, as did her five-year marriage to Jesse James, which came to a screeching halt when he admitted to infidelity. Bullock has been partnered with photography Bryan Randall since 2015.
10. Tate Donovan and Jennifer Aniston
How long they were together: 3 years
When they broke off the engagement: 1998
Tate Donovan was already romantically linked with Jennifer Aniston when he starred as Rachel Green’s love interest Joshua in season four of Friends. Unfortunately for them, they actually broke off their engagement while still filming together. Awkward. Two years later, Aniston became half of America’s favorite married couple for five years with Pitt; 10 years after their divorce, she married Justin Theroux, and their split was recently announced. After two failed engagements, Donovan married writer Corinne Kingsbury in 2005, which lasted for three years. (Is “three years” Donovan’s unlucky number??)
9. Sienna Miller and Jude Law
How long they were together: Dated for 1 year, 2 months the first time around; engaged for 1 year, 10 months
When they broke off the engagement: November 2006
Jude Law is notorious for being a less-than-stellar partner. Although he only has one official ex-wife (British actress Sadie Frost, whom he was married to for six years in the late ‘90s/early ‘00s), he has children with three exes, has a failed engagement with Sienna Miller, and is known to be unfaithful. Law and Miller actually sustained their engagement for over a year after Law came clean about his affair his children’s nanny. Miller had a fling with actor Daniel Craig after the news broke — but they didn’t make it down the aisle. They reconnected a few years later, but it still wasn’t meant to be, and they split again after a little over a year.
8. Sean Penn and Charlize Theron
How long they were together: Dated for 1 year; engaged for 6 months
When they broke off the engagement: June 2015
Although there was speculation that Charlize Theron just ghosted her then-fiance Sean Penn by ignoring his texts and phone calls, Theron denied any such allegations when she opened up about the year and a half relationship. Had the marriage come to fruition, Theron would have been Penn’s third wife, following a four-year marriage to singer Madonna in the ‘80s and a 14-year marriage to actress Robin Wright spanning the mid-‘90s to 2010. Theron has never been married, but she is the mother of two children whom she adopted.
7. Rachel Bilson and Hayden Christensen
How long they were together: Dated for 1 year the first time around; engaged for 1 year, 6 months
When they broke off the engagement: August 2010
Although they are technically an on-again, off-again couple, Rachel Bilson and Hayden Christensen are so nondramatic about it. Their initial year-long courtship was barely even public before she was sighted with an engagement ring, which also was not a public announcement — however, the end of the engagement was. The duo got back together after just a few months separation, without a ring this time, and became parents four years later. Though they managed to (mostly) stay together for a decade, Bilson and Christensen split again in 2017.
6. Britney Spears and Justin Trawick
How long they were together: Dated for 1 year, 7 months; engaged for 1 year, 1 month
When they broke off the engagement: January 2013
Don’t know who Justin Trawick is? You’re not alone. His most recognizable claim to fame is his relationship and broken engagement to household name Britney Spears, which began in spring of 2010 when he was her agent. They ended their professional relationship to focus on their personal one, which lasted nearly three years. After the breakup, Trawick also resigned his role as co-conservator, which, alongside Spears’s father, had given him the power to make decisions about her general well-being – including food, clothing, travel, and medical care.
5. Demi Moore and Emilio Estevez
How long they were together: 2 years
When they broke off the engagement: 1987
After divorcing her husband of five years, rock musician Freddy Moore, Demi Moore met Emilio Estevez on the set of St. Elmo’s Fire. Though she didn’t walk down the aisle with Estevez, Moore proceeded to get married (and divorced) two additional times, to actor Bruce Willis for a full 13 years until 2000, and then to actor Ashton Kutcher for a steady eight, ending in 2013. Estevez made it to the church on time for his marriage to singer Paula Abdul, which lasted two years in the early ‘90s.
4. Sheryl Crow and Lance Armstrong
How long they were together: Dated for 2+ years; engaged for 5 months
When they broke off the engagement: February 2006
Sheryl Crow and Lance Armstrong began dating in 2003 after Armstrong divorced his wife of five years, Kristin Richard. The couple was engaged for the last five months of their courtship, breaking it off years before Armstrong was accused of doping. Rumors speculated that Crow knew about the illegal activity during their relationship. Regardless of whether that’s true or not, one thing is… ultimately, Armstrong wasn’t strong enough to be her man. Armstrong is currently engaged to Anna Hansen; Crow has not gotten married, but she has adopted two children.
3. Zoe Saldana and Keith Britton
How long they were together: Dated for 10 years; engaged for 1 year, 5 months
When they broke off the engagement: November 2011
Damn, talk about a couple that was *this close* to making it: Zoe Saldana and Keith Britton were together for over a decade! Following the cancellation of their engagement, Saldana and Britton remained business partners for the website they co-founded, My Fashion Database. After Britton, Saldana dated actor Bradley Cooper for a little over a year before meeting Italian artist Marco Perego. The duo had a secret wedding ceremony in London just a few months later, and they now have three children.
2. Kaley Cuoco and Josh Resnik
How long they were together: Engaged for 5 months
When they broke off the engagement: March 2012
There’s not much public information about the relationship between Kaley Cuoco and Josh Resnik. If you don’t know who that is, join the club (he’s an addiction specialist, FYI, whatever that means). The couple was just engaged for five months before calling it off. Of course, Cuoco was only dating tennis player Ryan Sweeting for three months when they got engaged, and they actually tied the knot — for three years. Cuoco is now engaged for the third time, to equestrian Karl Cook. May the third time be the charm!
1. Jennifer Lopez and Ben Affleck
How long they were together: Dated for 8 months; engaged for 1 year, 2 months
When they broke off the engagement: January 2004
No one remembers Gigli (thank goodness), but everyone remembers that the first Jennifer in Ben Affleck’s life wasn’t his now ex-wife, Jennifer Garner. Affleck certainly didn’t take much time between the two Jens; he started dating Garner mere months after calling off his engagement to Lopez and married her a year and a half later, four months into her pregnancy with their first child. Twelve years and two more kids later, the Jennifer engagement that actually panned out ended in divorce. But think about Lopez’s situation before saying Affleck moved on too fast. Lopez was actually still married to Cris Judd when she and Affleck became costars, and she was linked with now ex-husband Marc Anthony, whom she had met before, mere days after the breakup, marrying him even sooner than Affleck and Garner got hitched. Anthony was Lopez’s third marriage to end in divorce… maybe Affleck truly was her one that got away?