These celebrity pairs had their dose of romance, breakups, makeups, heartbreak, and in some cases, happy endings with entirely different people. But in any case, fancy engagement rings, matching love tattoos, and romantic proposals weren’t enough to get them to the altar. And we’re here to find out what really happened behind the scenes.
Olivia Wilde and Jason Sudeikis
Olivia Wilde and Jason Sudeikis had quite the Hollywood love story. They first crossed paths at a "Saturday Night Live" afterparty in 2011, and they were dating six months later. Fast forward two years and Sudeikis popped the question. The engagement, which lasted an entire seven years, had fans eagerly awaiting their walk down the aisle.
But unfortunately, their relationship took an unexpected turn, and despite their best efforts, they decided to part ways in 2020 and officially called off the wedding. However, both Olivia and Jason have continued to excel in their respective careers, with Olivia shining as an actress and director, and the “Ted Lasso” star having an incredible career as an actor and comedian. Despite some recent drama, these two will have to remain close for the sake of their two kids.
Gwyneth Paltrow and Brad Pitt
In the 90s, Gwyneth Paltrow and Brad Pitt were the ultimate Hollywood power couple. The two met on the set of the movie "Se7en" in 1994 and quickly began dating. In 1996, they got engaged, but their relationship ended just a year later.
While both actors have been relatively private about the reasons behind their split, Paltrow has said that she was too young at the time to handle such a high-profile relationship and realized she wasn’t ready to get married. Despite their breakup, the two have remained on good terms. Paltrow is raising two kids and running a wellness empire, and Pitt went on to marry Angelina Jolie (whom he divorced) and become a father of six.
Courteney Cox and Michael Keaton
When “Friends” star Courteney Cox tied the knot with “Scream” co-star David Arquette in 1999, they became one of Hollywood’s most famous couples. However, before she wed the handsome actor, Cox was previously engaged to actor Michael Keaton. The year was 1989 and a mutual friend introduced them after Cox had said she really liked Keaton’s performance in the film “Clean and Sober.”
The two actors really hit it off and began dating shortly after, eventually getting engaged. But, by 1995, Keaton and Cox ended things for good, due to “different lifestyles,” reported the actress. They both went on to have extremely successful acting careers and although Cox divorced Arquette in 2013, they share a daughter together and remain close. Keaton is still single, as far as we know.
Rashida Jones and Mark Ronson
The “Parks and Recreation” and “The Office” star Rashida Jones and musician Mark Ronson began dating back in 2002. Rashida comes from Hollywood royalty – legendary record producer Quincy Jones and actress Peggy Lipton; while Ronson is an extremely successful musician, DJ, and record producer that has worked with Amy Winehouse, Adele, Lady Gaga, and countless others.
This odd couple seem to hit it off almost right after meeting and after a year of dating, Ronson proposed through a crossword puzzle, that ultimately read out “Will you marry me”. So cute! Unfortunately, by the beginning of 2004, they decided to split up. Rashida is currently involved with musician Ezra Koenig, and Ronson married actress Grace Gummer in 2021.
Bella Thorne and Benjamin Mascolo
Disney star Bella Thorne and Italian singer Benjamin Mascolo thought they had found their "happily ever after" in each other. The sparks flew when they crossed paths in 2019, and their love story quickly took off. The couple seemed inseparable, with adorable social media posts and public displays of affection.
Finally, in March 2021, the singer popped the question, and the couple got engaged. However, life had other plans. Almost exactly a year after getting engaged, Mascolo announced on social media that they had separated and called off the wedding. Bella is now engaged to producer Mark Emms, and Mascolo has kept his private life under wraps.
Edward Norton and Courtney Love
Now, here’s a shocker. The controversial rockstar and Nirvana frontman’s ex Courtney Love was engaged to actor Edward Norton, can you believe it? Thanks to Norton, and the fact that it happened in the late nineties, the relationship was kept very private. Until Love went public some years later, telling the whole story. Norton and Love met on the set of the 1996 film “The People vs. Larry Flynt” and started a whirlwind relationship that lasted three years.
At some point during their relationship, Norton popped the question, and the couple got engaged. But not long after, Love called it off, saying she wasn’t ready for the commitment. Norton went on to marry Canadian film producer Shauna Robertson in 2012, with whom he has two kids. Love is apparently still single and still causing mayhem.
Uma Thurman and Arpad Busson
Uma Thurman hasn’t had much luck in her personal life. When it comes to love, Thurman has been married twice – to Gary Oldman and Ethan Hawke – and both times it ended in divorce. In 2007, she decided to give love another chance and started dating French financier Arpad Busson. By 2008, they were engaged, but called it off shortly after, with Uma returning the 8-carat diamond ring Busson had given her.
But they got back together, and four years later, they had a daughter. However, they couldn’t make the relationship work. In 2014, Thurman ended things for good, saying Busson was too controlling; they went on to have a nasty custody battle for their daughter, which Thurman ultimately won.
Johnny Depp and Jennifer Grey
“Dirty Dancing” star Jennifer Grey skyrocketed to fame after her role in the 1987 hit film. The star was dating Matthew Broderick in 1987 and became engaged shortly after. Unfortunately, a terrible car crash the couple had in Ireland which ended up taking two other peoples’ lives proved to be too much strain for Grey and Broderick, and they finally broke up in 1988.
As it turns out, Grey had started seeing Johnny Depp a few weeks after ending it with Broderick. Depp and Grey, who met through Grey’s agent, got engaged after just two weeks of seeing each other, meaning Grey was engaged to two different men during the same month in 1988. They lasted a year and then broke things off for good.
Charlie Sheen and Scottine Ross
Charlie Sheen is probably one of the most controversial actors in Hollywood history. The man has been on the news more times than anybody can count, and his love life has been a huge part of the media fodder. Amongst his many failed relationships, few people know about his very brief engagement with model and adult film star Scottine Ross.
They met in November 2013, dated until January 2014, got engaged, and called it off later that year. And in typical Charlie Sheen fashion, it didn’t end there. Ross sued Sheen for a whopping $5 million dollars, and they ended up settling for an undisclosed amount. Yikes!
Jennifer Aniston and Tate Donovan
If you were a fan of “Friends,” you’ll remember the episodes when Rachel becomes smitten with one of her customers – Joshua, played by actor Tate Donovan. But few people know that these two had an actual love story behind the cameras. Before getting cast on “Friends,” Tate Donovan had dated Jennifer Aniston for three years and even popped the question in 1998.
They were engaged for a few months before calling it off – apparently, the media pressure was too much for Donovan. So, it was incredibly awkward when Donovan got cast in five episodes of “Friends” and had to work next to his ex-fiancé every day. Luckily, they both moved on; Anniston went on to marry twice and then get divorced, and Donovan married once but also ended in divorce.
Nicollette Sheridan and Michael Bolton
The talented blonde bombshell Nicolette Sheridan is most known for her roles in “Desperate Housewives” and “Dynasty.” But she’s been in the Hollywood scene since the 90s, and so was her almost-husband Michael Bolton. The famous singer-songwriter and the actress dated from 1992 until 1995, when they broke things off.
Then, in 2005, they rekindled the relationship and even got engaged. People thought things were finally going to work out between them, but alas, in 2008, they decided to go their separate ways. Bolton never married, and Sheridan married actor Aaron Phypers in 2015, but got divorced three years later.
Demi Moore and Emilio Estevez
The 1985 coming-of-age hit film “St. Elmo’s Fire” brought co-stars Demi Moore and Emilio Estevez together. They started dating for some months and were engaged by the end of that same year. For the next two years, Moore and Estevez broke up and got back together several times, until finally setting a wedding date for December of 1986.
Not surprisingly, they finally called it off for good a few months later. Moore married actor Bruce Willis in 1987, with whom she had three gorgeous daughters. Even though they divorced in 2000, they remain very close. Moore married Ashton Kutcher in 2005 and then divorced him in 2013. Since then, the beautiful actress has been enjoying the single life with her cute dog Pilaf.
Jason Wahler and Katja Decker Sadowski
“The Hills” and “Laguna Beach: The Real Orange County” actor Jason Wahler is now happily married to model Ashley Slack. However, back in 2007, he almost pledged his undying love to somebody else – Katja Decker Sadowski. They started dating in February of 2007, and by August of that same year, they were engaged.
The engagement bliss lasted until February 2009, when Wahler decided to call off the wedding. The actor said they had broken up amicably and simply decided that “they were both just too young to be considering getting married right now.” Well, it’s definitely better to admit that before any forever commitments are made.
Julia Roberts and Kiefer Sutherland
Julia Roberts and Kiefer Sutherland met on the set of their movie "Flatliners" in 1990, right when Sutherland was finalizing a divorce. The two began dating soon after and were living together by the end of that same year. Rumors started going around about Sutherland being unfaithful, but they were all silenced when the couple announced they were engaged and scheduled for a big celebrity wedding in June of 1991.
But just three days before their scheduled wedding, Roberts called off the engagement. Roberts eventually married cinematographer Daniel Moder in 2002 and went on to have three children. Sutherland’s love life was slightly rockier – he got married and divorced and has had a slew of relationships in between until finally settling down with partner Cindy Vela, also an actress.
Ruby Rose and Phoebe Dahl
Actress and “Orange Is the New Black” star Ruby Rose met Phoebe Dahl in 2014, at a barbecue of a mutual friend. Dahl, granddaughter and heiress to famous English writer Roald Dahl, immediately fell for the wild and gorgeous Ruby. And apparently, the feeling was mutual.
The two started dating, and after just three months, they got engaged. However, the engagement lasted little over a year, as they announced they were going their separate ways by the end of 2015. As Dahl explained to the press, "Our break is not the result of any media speculation, and we want nothing but the best for each other."
Sean Penn and Charlize Theron
Sean Penn definitely has good taste in women. After splitting up with his actress Robin Wright, Sean Penn fell for none other than South African beauty Charlize Theron. These two Hollywood A-listers got together in 2013 and got engaged a short year later; but alas, it wasn't meant to be. After 18 months of dating, they decided to go their separate ways.
The tabloids had a field day with their breakup, but thankfully, Theron cleared everything up. Like the classy lady that she is, the “Mad Max: Fury Road” star cleared the air, saying that sometimes relationships just don't work out, and in this case, they both decided to separate amicably. Oh well, as long as it was amicable.
Dylan McDermott and Maggie Q
Actor Dylan McDermott made his claim to fame after starring in the legal drama series “The Practice,” and he’s continued to land important roles through the years. Career-wise, McDermott has done quite well for himself, acting in hit shows like “Law & Order,” “American Horror Story,” and “FBI: Most Wanted.”
As for his love life, things haven’t gone so well. Back in 2014, McDermott met co-star Maggie Q on the set of the TV crime series “The Stalker.” They started dating almost immediately, and less than a year later, they were engaged. After four years of what seemed to be a lasting love story, they split up.
Darren Aronofsky and Rachel Weisz
Brilliant director Darren Aronofsky and stunning actress Rachel Weisz were one of Hollywood’s favorite couples, and we can see why. They met backstage at a play in London back in 2001, and it seems the chemistry set right in because a short year later, Rachel was moving to New York to live with Darren.
In 2005, they got engaged, and a few months later, they had a son. By 2006, Aronofsky cast his fiancé in his film “The Fountain,” and to keep things professional, they moved to separate apartments while the shoot was going on. This caused them to drift apart and have less time as a couple, which eventually led to their breakup in November 2010.
Mariah Carey and James Packer
Mariah Carey’s love life seems to be as dramatic as her songs, but despite two failed marriages and an engagement that never happened, the diva never lost hope. Carey has been in a relationship with choreographer Bryan Tanaka since 2016, and they seem to be going strong.
However, right before partnering with Tanaka, she had a brief but intense engagement with Australian businessman James Packer. In 2015, Carey and Packer started dating and a wild romance began, and by 2016, Packer proposed to the “Endless Love” singer with a $10 million, 35-carat diamond ring! The couple was engaged for about ten months, until finally calling it off due to fights and irreconcilable differences.
Marilyn Manson and Rose McGowan
Rose McGowan and Marilyn Manson's love affair was a wild ride. The pair made headlines for their three-and-a-half-year-long public relationship, but their engagement ended after just two years in 2001. While rumors suggested that substance abuse played a part in their breakup, McGowan still holds a candle for Manson, stating that "there is great love."
However, she admitted that their lifestyles didn't quite match up. Manson moved on to marry Dita Von Teese, but that also came to an end after rumors that he was involved with actress Evan Rachel Wood. Later that year, the cat was out of the bag, and Manson's relationship with Wood went public. In 2007, McGowan got engaged to Robert Rodriguez, but that also didn’t end in a wedding.
Alyssa Milano and Scott Wolf
“Charmed” star Alyssa Milano once quipped that her dating history is longer than her IMDB profile. And boy, does she have a star-studded list! From Eric Dane to Justin Timberlake to David Arquette, Milano knows how to keep things interesting. But there's one relationship that took a nosedive — her whirlwind romance with Scott Wolf.
It all started on the set of “Double Dragon” in June 1993, and before two months of dating had gone by, Milano and Wolf were already living together. The engagement followed suit, but by the next year, they had decided to end it. Milano, now happily married to her agent husband, David Bugliari, is raising two adorable kids. As for Wolf, he married Kelley Marie Limp and has three gorgeous children.
Lenny Kravitz and Nicole Kidman
This one was a true shocker since very few people knew that Nicole Kidman and Lenny Kravitz had been engaged. Yes, you read that right. “The Northman” star dated and even got engaged to musician Lenny Kravitz back in the early 2000s. In 2002, Lenny Kravitz was Kidman’s landlord, and the two started dating after meeting a few times.
Things progressed quickly and by 2003 they got engaged, but it didn’t last long, things were officially over that same year. Kidman never said anything until casually dropping a bomb for her “Big Little Lies” press tour. “Well, I knew Zoë because I was engaged to her father,” the actress suddenly said. Well, they both seem to have ended up quite happy.
Sheryl Crow and Lance Armstrong
2003 was a landmark year for cycling legend Lance Armstrong – he finalized his divorce from his first wife and started dating singer Sheryl Crow shortly after. Their engagement hit the headlines in September 2005, but just a few months later, their love story came to a screeching halt in February 2006.
The seven-time champion of the Tour de France couldn’t make things work with Crow. But hey, life goes on, and Armstrong went on to have two more kids with his fiancé Anna Hansen. Meanwhile, Crow adopted two beautiful boys and settled down in Nashville, Tennessee. All’s well that ends well!
Kerry Washington and David Moscow
Back in the early 2000s, “Scandal” star Kerry Washington was in a relationship with fellow actor David Moscow. You might remember Moscow from playing the young Josh Baskin, Tom Hanks’ friend in the 90s film “Big.” In 2004, Moscow finally popped the question and the couple got engaged.
The engagement lasted three years, and suddenly, in 2007, Kerry realized she wasn’t even excited about picking out her dress. Both Washington and Moscow realized they were trying too hard to make things work, so they finally called it off in what was a very public breakup. Not surprisingly, Washington has kept her personal life very private since then, even after marrying fellow actor Nnamdi Asomugha and having two gorgeous kids together.
Tate Donovan and Sandra Bullock
You probably won’t remember the cheesy 1992 romcom “Love Potion No. 9,” but its stars certainly do. Sandra Bullock and Tate Donovan fell for each other on set and after a few months of dating, they got engaged. Unfortunately, the engagement lasted three years, and in 1995, they finally called it quits.
When Bullock talked about why the relationship ended, she said, "the person who needed me most was always the person I was attracted to," explaining that her self-love was never her priority. Definitely a recipe for disaster. Bullock had been with photographer Bryan Randall since 2015 and they had been raising her two adopted kids. Sadly though, Randall passed away in 2023.
Emily Blunt and Michael Bublé
Before “A Quiet Place” star Emily Blunt was happily married to fellow actor John Krasinski, she was engaged to famous singer Michael Bublé. They met back in 2005 when Blunt was backstage for one of Bublé’s concerts, and they almost immediately hit it off. After dating for some time, Michael proposed to the actress ad they got engaged. Unfortunately, by 2008, they had broken things off due to alleged infidelity on Bublé’s part.
They both stayed very private about the breakup, with Michael ultimately saying that show business is very strenuous on any relationship, especially if one person is in music and the other in film. Bublé went on to marry Argentinian actress Luisana Lopilato, and Blunt has a beautiful family with Krasinski.
Colbie Caillat and Justin Young
In a love story for the ages, singer-songwriters Colbie Caillat and Justin Young fell in love back in 2010, after having been best friends for years. Their family, friends, and fans couldn’t get enough of this adorable couple, who had their social media accounts littered with romantic photos.
Five years later, they got engaged, and everyone was waiting patiently for the wedding date to be set. But another five years went by and, instead of a wedding date, Caillat and Young broke up in 2020. Since then, no new relationships have been reported by either, and they seem to remain good friends and musical collaborators.
Drew Barrymore and Jamie Walters
Among the long list of celebrities that Drew Barrymore has dated, including Luke Wilson, David Arquette, Tom Green, and Justin Long, “Beverly Hills, 90210” star Jamie Walters was one of the few that popped the question. Barrymore and Walters started dating in 1992, and after a few months, they were already living together and getting engaged.
Sadly, the engagement only lasted a year, and in 1993, they went their separate ways. Fun fact: Walters was so committed to Barrymore that he had her name tattooed on his arm – and she returned the gesture! Perhaps it would have been a better idea to wait until after the wedding to get the matching tats?
Johnny Depp and Sherilyn Fenn
The beautiful actress Sherilyn Fenn made her acting debut by playing Audrey Horne in the hit 90s show “Twin Peaks.” But before she became an A-list Hollywood celebrity, she met Johnny Depp on the set of a 1985 student film. They started an on-and-off relationship that lasted three years until they finally got engaged.
A few months later, they broke things off for good, and Fenn went on to marry musician Toulouse Holliday in 1994 and have a son with him. Three years later, they divorced, and it wasn’t until 2006 that Fenn started a serious relationship with Dylan Stewart, with whom she had another son. As for Depp, well, we all know how that turned out.
Rob Kardashian and Blac Chyna
The least-known member of the famous Kardashian clan, Rob Kardashian made headlines when he started dating model and actress Blac Chyna. Back in 2016, after just two and a half months of dating, Rob proposed, and the couple got engaged.
More than a year into the engagement, they had a daughter in November 2017, and Blac Chyna’s tense relationship with the rest of the Kardashian family didn’t seem to be getting any better. After some months of insane drama, Rob and Blac Chyna decided to break things off for good in February of 2018. Nowadays, they’re focused on co-parenting their daughter Dream and seem to both be single.
Daniel Craig and Satsuki Mitchell
Daniel Craig, the suave British actor known for his iconic portrayal of James Bond, had an interesting journey with his former partner, film producer Satsuki Mitchell. The two crossed paths on the set of the 2005 film “The Jacket.”
They began dating and, two years later, Daniel popped the question, and Satsuki happily accepted. However, three years later, in 2010, Craig called things off and didn’t wait too long to start dating his now-wife Rachel Weisz. The two have been together since 2011, and more than a decade later, they still seem to be head over heels for each other.
Evan Rachel Wood and Zach Villa
In the magical city of Los Angeles, Evan Rachel Wood and Zach Villa met in 2015. They fell for each other almost instantly and began a musical journey together. They fused their talents and formed the electro-pop music duo, "Rebel and a Basketcase." While they kept mum about their engagement, their arrival at the SAG Awards with matching suits and those sneaky little engagement bands spilled the beans.
Even Wood's publicist couldn't keep it under wraps. But alas, like a song that fades out too soon, their relationship was over by September 2017. The “Westworld” star has decided to enjoy the single life while raising a son from a previous marriage, while Villa seems to be fully dedicated to his music and acting.
Laura Dern and Billy Bob Thornton
In a Hollywood tale that was almost as wild as a Coen Brothers' film, Laura Dern and Billy Bob Thornton once walked the red carpet hand in hand. The A-list celebrities met back in 1997 when they appeared as guests on the Ellen DeGeneres show. They really hit it off from the get-go and started dating.
Shortly after, they got engaged but then came the drama. In 2000, after discovering that Thornton had secretly married Angelina Jolie while engaged to her, Laura Dern had no other choice but to accept that the relationship with the “Monster’s Ball” star was definitely over. Thornton split from Jolie and married actress Connie Angland in 2014.
Anne Cline and Taryn Manning
The worlds of music and acting collided when musician Anne Cline and actress Taryn Manning found themselves head over heels for each other. After a wild romance, singer Cline proposed to the “Orange Is the New Black” star in the middle of a concert. Cline hopped off the stage and proposed to Manning in June of 2021.
Unfortunately, by October of that same year, they called off the engagement. Apparently, it was Manning’s decision, explaining in a later interview that it was “just not the right relationship for her.” As for their current love lives, both the actress and musician seem to be single and focusing on their careers.
Ginnifer Goodwin and Joey Kern
“Big Love” and “Once Upon a Time” star Ginnifer Goodwin started dating Joey Kern, who rose to fame after his role in the indie horror “Cabin Fever,” in 2010. The star-crossed duo met through a mutual friend that set them up. After months of dating, Kern popped the question with a beautiful engagement ring the actor had designed himself. Romantic!
However, like many love stories in Tinseltown, their engagement ultimately ended a few months later. Thankfully, both moved on to new chapters. Ginnifer found her "happily ever after" in actor Josh Dallas, her "Once Upon a Time" co-star, with whom she had two children. Meanwhile, Joey tied the knot with fitness instructor Gillian Rose in 2019.
Clare Crawley and Dale Moss
Clare Crawley and Dale Moss had a whirlwind romance that left viewers buzzing. The couple met on the set of "The Bachelorette," where Crawley famously declared, "I just met my husband!" They got engaged after a short but intense courtship.
However, their love story took an unexpected turn when they decided to go their separate ways just a few months later in 2021. Rumors of infidelity and conflicting priorities circulated, and it seemed their relationship hit a snag. Currently, Clare is married to Mascot Sports CEO Ryan Dawkins, while Dale has been spotted getting cozy with TV personality Galey Alix.
Michelle Young and Nayte Olukoya
Back in the dramatic world of reality TV romance, “The Bachelorette” stars Michelle Young and Nayte Olukoya fell for each other on the popular show. Their love story captured the hearts of viewers, who were all over the moon with joy when Olukoya proposed in December 2021.
They seemed like the perfect couple, but sadly, they broke things off a mere six months later. It seems that having such a publicized relationship got the best of them both, and then there were Olukoya’s commitment and alleged infidelity issues. And it looks like the famous life definitely got to them because they have made a point to keep their love lives private ever since.
John Cena and Nikki Bella
In a plot twist that had WWE fans gasping for breath, John Cena and Nikki Bella slammed the brakes on their six-year relationship, leaving their wedding bells hanging in limbo. Just when everyone thought they were about to say, "I do," they decided to call things off.
As fate would have it, Bella found her happily ever after with Russian professional dancer Artem Chigvintsev, putting a sparkling ring on her finger and welcoming a son. Meanwhile, Cena found his match in Shay Shariatzadeh, whom he married in 2020. According to close sources, Cena and Bella remain good friends to this day.
Brie Larson and Alex Greenwald
Brie Larson has been acting since her early teens, and she’s slowly climbed her way up the Hollywood ladder to reach peak success. The “Captain Marvel” star met Alex Greenwald, lead singer for the band Phantom Planet, back in 2013, right after Larson’s success with “Scott Pilgrim vs. the World” and “21 Jump Street.”
Two years later, their relationship seemed to be going amazingly and Larson was at the peak of her career, winning an Oscar for her role in the 2015 film, “Room.” By 2016, Alex popped the question and the young couple got engaged. But three years later, the couple confirmed they had decided to end things in January 2019, much to their fans’ dismay.
Hayden Christiansen and Rachel Bilson
Back in 2008, “The O.C.” star Rachel Bilson and the “Star Wars” legend Hayden Christiansen crossed paths on the set of the film “Jumper.” Sparks flew and they immediately began dating, deciding to take the plunge and get engaged that very December. But unfortunately, they quietly hit the pause button in August 2010.
However, by the end of the year, they found a way to patch things up, proving that even movie stars can't resist a good sequel. Fast forward to October 2014, and they welcomed their precious bundle of joy, Briar Rose Christiansen – and yes, they were still engaged. It wasn’t until September 2017 that these movie stars officially called it quits.
Katie Holmes and Chris Klein
Actress Katie Holmes rose to fame after starring in the popular show “Dawson’s Creek,” after which she started dating co-star Joshua Jackson. And her next relationship was even more serious, and with another good-looking actor; Holmes met “American Pie” star Chris Klein in 2002, and by 2003, they were engaged.
For reasons unknown, they broke up two years later, and the wedding never happened. Two months later, Holmes was engaged to Tom Cruise, whom she married and eventually divorced after having a daughter together. As for Chris Klein, he married a travel agent and had a son and a daughter.
Paris Hilton and Jason Shaw
The heiress, party girl, and socialite Paris Hilton has had no shortage of drama in her life. In between the non-stop partying and jet-set lifestyle, she’s gotten her heart broken (and broken some herself) more than once. Hilton started dating actor Jason Shaw in 2002, and a few months later, they were engaged.
But as often happens in the world of celebrities, they broke off the engagement a short year later. Since then, Hilton went on to have several relationships and engagements until finally tying the knot with entrepreneur and author Carter Reum in 2021. Hopefully, this one is a keeper for the party princess.
Alec Baldwin and Janine Turner
Before Alec Baldwin married famous yoga instructor Hilaria Baldwin and had lots of kids together, he had his fair share of heartbreaks. Back in the early 80s. Baldwin was a young, handsome actor reading for a part in the famous TV show “General Hospital,” when suddenly a stunning woman came in to audition – Janine Turner.
Baldwin became infatuated with her, and they began dating in 1983. Shortly after, they were engaged. Everything was ready – the dress, the church, the invitations, the catering – and then they suddenly decided to call it off. Turner explains that they realized they weren’t good for each other, and apparently, it was a good decision.
Sarah Chalke and Jamie Afifi
If you were a “Scrubs” fan, chances are you were in love with Elliot Reid’s character. And no one could have played her better than sweet actress Sarah Chalke. The NBC star met entertainment lawyer Jamie Afifi in 2003, and they began dating shortly after. Three years later, Jamie asked Sarah to be his wife, and the couple were officially engaged.
From the moment they got engaged in 2006 until they broke up in 2022, sixteen years later, a lot of things happened. They worked on numerous projects together, had two kids, traveled the world, and ultimately, for reasons unknown, decided to call it quits. Luckily, they remain, good friends, as they co-parent their children together.
Lady Gaga and Christian Carino
Only true fans of Lady Gaga will know this one. Rumors about the world-famous singer started going around that she had begun dating her talent agent, Christian Carino. The rumors were definitely confirmed after the pair were seen getting very romantic with each other during the 2017 Super Bowl weekend. After a year of keeping their relationship quite private, Lady Gaga publicly announced that they had gotten engaged in October 2018.
Unfortunately, by early 2019, Lady Gaga ended the relationship. Apparently, none of Gaga’s friends liked Carino because he was extremely jealous and possessive. A close friend of the singer said that Carino “didn’t treat Gaga very well toward the end. He texted her a lot and was always trying to find her.”
Brad Womack and Emily Maynard
Brad Womack's journey to find love on "The Bachelor" led him to Emily Maynard, and for a moment, it seemed like they had found their fairytale ending. The couple got engaged in the show's finale, but alas, the magic wore off. Their relationship faced its share of challenges, and they ultimately decided to part ways in 2011.
Since then, both Brad and Emily have moved on to find love outside of the Bachelor Nation. Brad keeps his romantic life private, while Emily married Tyler Johnson and is enjoying a blissful family life. Sometimes, even roses can't guarantee a "happily ever after."
Steven R. McQueen and Alexandra Silva
"The Vampire Diaries" star Steven R. McQueen is a certified Hollywood hunk, so when he announced he was dating the stunning model Alexandra Silva in 2016, it just made sense. McQueen confirmed their relationship after posting a very cute photo of them skiing together in December 2016.
And a few months later, they were engaged! Everybody thought things were going great until 2018, when at a fancy gala, McQueen suddenly said that they had called off the engagement. The actor made it clear that the decision was mutual, and he didn’t seem too bothered by the whole thing. As far as we know, both he and Silva are currently single.
Jasmine Cephas Jones and Anthony Ramos
These two “Hamilton” stars met back in 2014 on the set of the famous Broadway Musical directed by Lin-Manuel Miranda. According to sources, the moment that Jones arrived on stage, Ramos couldn’t stop looking at her, and it was almost love at first sight. On Valentine’s Day of 2015, the young couple went public with their relationship, and for the next few years, everything was going amazingly.
In 2018, Ramos popped the question to Jasmine while vacationing in England. The next three years were filled with romantic gestures, adorable social media posts, and a love that seemed unbreakable. But to everyone’s shock, Ramos and Jones officially announced they were ending things in 2021.
Liam Payne and Maya Henry
Liam Payne and Maya Henry's love story started with a spark, but unfortunately, the flame fizzled out. The former “One Direction” singer and the model met in 2019, and a short year later, they made their engagement public with Maya flaunting a stunning diamond ring.
However, the show didn't go on for long, as they called off their engagement in June 2021. But two months later, Payne and Henry got back together and tried to make it work for a good few months. Sadly, they decided to call it off for good in April 2022. Payne hasn’t had much luck in love, and Henry has focused solely on her career.
Zoe Saldaña and Keith Britton
The “Guardians of the Galaxy” and “Avatar” star Zoe Saldaña might be happily married with three kids nowadays, but not long before tying the knot with artist Marco Perego in 2013, she had a serious romance with someone else. Back in 2000, Saldaña started dating entrepreneur Keith Britton, and they were madly in love for an entire decade.
In June of 2010, Britton popped the question and they got engaged. But the big wedding her fans were expecting never happened. They decided to call it quits in 2011, apparently because they couldn’t agree on when to start a family. Luckily, just two years later, she found someone who was a perfect match.
Heather Locklear and Jack Wagner
The “Melrose Place” star Heather Locklear started dating her co-star Jack Wagner back in 2007. Four years of romantic bliss went by, and things were going so well that Wagner proposed. By August 2011, they were engaged and seemed to be incredibly happy. But just three months later, they called off the whole thing.
Locklear had already come from two failed marriages, and it took her a while to reel from her breakup with Wagner. It wasn’t until 2017 that the actress rekindled a relationship with Chriss Heisser, a high school sweetheart. And they recently got engaged! As for Wagner, he dedicated himself to raising his children from a previous marriage and to his successful acting career.
Alex Rodriguez and Jennifer Lopez
Ah, the fascinating drama that is J.Lo’s love life. The actress and singer famously made headlines by getting back together and marrying Ben Affleck, but Jennifer Lopez has had quite the journey when it comes to her personal life.
The “Hustlers” star started dating Major League Baseball player Alex Rodriguez back in 2017, and two years later, he popped the question. Lopez said yes, and for the next two years, they seemed to be crazy about each other and planning an unforgettable wedding. But to their fans’ shock, they publicly announced they were going their separate ways on April 2021.
Kate Moss and Pete Doherty
Nothing like the rock 'n' roll romance that was Kate Moss and Pete Doherty. This edgy couple, known for their rebellious spirits and wild antics, had the tabloids in a frenzy back in 2007 when they announced their engagement. With Moss's supermodel status and Doherty's rockstar persona, they seemed destined for each other.
However, their engagement crumbled under the weight of substance dependencies and tumultuous lifestyles, and later that same year, they officially split up. Doherty went on to marry singer Katia de Vidas in 2021, and Moss has been dating Nikolai von Bismarck since 2015. Both Doherty and Moss have children from previous marriages.
Alanis Morissette and Ryan Reynolds
Canadian stars Alanis Morissette and Ryan Reynolds met back in 2002, at a birthday party for actress Drew Barrymore, and they immediately liked each other. The rockstar and the actor had such chemistry that they got engaged after two years of dating. In 2005, Morissette gushed about Reynolds, calling him "such a supportive creature" and comparing his love to a "trampoline.”
Despite their love for each other, they never quite made it down the aisle, and they officially called off the engagement in February 2007. Fortunately, they've since found their happy endings — Reynolds married Blake Lively and started a family with four children. Meanwhile, Morissette tied the knot with Mario "Souleye" Treadway, and they now have three kids together.
Robin Wright and Ben Foster
When “House of Cards” star Robin Wright divorced Sean Penn, she found love with fellow actor Ben Foster. Even though they had met years ago, the chemistry between them started on the set of their 2011 film “Rampart.” The two got engaged, broke it off, got back together, and then called it off again.
It was like a game of relationship ping-pong until they both decided it was really over. Wright went on to marry Clement Giraudet, a VIP operations manager for Saint Laurent, in 2018. And Foster eventually found his match in “Orange Is the New Black” star Laura Prepon, who he married and started a family with. It's safe to say everything worked out for the best.
Shailene Woodley and Aaron Rodgers
“The Fault in Our Stars” star Shailene Woodley and Green Bay Packers quarterback Aaron Rodgers threw a curveball when they announced their engagement in 2021. The couple met in a truly unconventional way, as Woodley revealed that they got together during the COVID-19 pandemic and kept their relationship under wraps for a while.
Alas, their engagement only lasted for a year, with the couple breaking it off in 2022. Rumor has it that their busy schedules and conflicting priorities led to the breakup. As for their current dating status, Woodley has been linked to artist and athlete Nahko Bear in the past, while Rodgers is back on the field, tackling opponents and, hopefully, the dating game.
Johnny Depp and Winona Ryder
Back in the 1990s, Johnny Depp crossed paths with the fabulous Winona Ryder at a swanky movie premiere. They quickly hit it off and started a five-month relationship that seemed to have them both giggling like teenagers. Depp said in an interview, "there's nothing that can match the feeling I have with Winona in my 27 years of existence," which he further proved by tattooing “Winona Forever” on his arm.
They got engaged and lasted three years together before breaking it off. Ryder met designer Scott Mackinlay Hahn in 2011 and they have been together ever since. Meanwhile, Depp's very public and dramatic relationship with actress Amber Heard ended in divorce. Depp’s tattoo now reads "Wino Forever." Oh well.
Tara Reid and Carson Daly
Another famous love story from the 2000s was the relationship between actress Tara Reid and TV host Carson Daly. These two met in a wild season of "MTV Spring Break" and started dating almost immediately. They became one of the hottest couples of the moment, and seven months into the relationship, they were engaged.
Fans were expecting the “American Pie” star and Daly to have an epic party for a wedding, but a few months later, in 2001, they ended things. Daly went on to marry film producer Siri Pinter, with whom he had four children, and Reid seems to have committed to enjoying single life and casual relationships.
Amber Riley and Desean Black
The multi-talented Amber Riley, known for her powerful vocals and star role on "Glee," met internet personality Desean Black back in 2019. The duo met through mutual friends, and their chemistry was undeniable, so a few weeks later, they were dating. Fast forward some months and Black had popped the question, to which Riley happily said "yes."
The lovebirds were engaged for over a year, until in April 2022, they went public with the breakup. Riley announced the news in a podcast interview, saying, “I wish him the best. I don’t have anything horrible or bad to say.” Reportedly, they are both currently single.
Sienna Miller and Jude Law
Jude Law really knows how to keep things interesting in his love life. After his divorce from Sadie Frost, Law started dating his “Alfie” co-star Sienna Miller in no time. He even proposed to Miller on Christmas Day of that same year! Unfortunately, Law's extracurricular activities with the nanny caused him to issue a public apology in July 2005.
Despite the rocky start, Law and Miller managed to make things work until November 2006 when they called it quits. And that still wasn’t the end of it. They reunited in 2009, only to end things for good in 2011. After years of casual relationships, Law finally settled down after marrying Phillipa Coan in 2019, and they’ve been busy raising Law’s five children from previous marriages in addition to the two they have together.
Marilyn Manson and Evan Rachel Wood
Evan Rachel Wood first met Marilyn Manson when she was just 18, and he was married. Despite their age difference, Wood and Manson dated on and off for four years, with the rock star proposing on stage in Paris in 2010. Alas, it wasn't meant to be, and the couple split for good the following year.
Years after the relationship ended, Wood disclosed that it was actually far from healthy so we are happy she has moved on from it. These days, Wood is no stranger to engagements: she was previously engaged to actor Jamie Bell, with whom she shares a son, and more recently to her bandmate Zach Villa. But it seems that Wood is focusing on herself for the time being, as she called off her engagement to Villa in 2019.
Ariana Grande and Pete Davidson
Even though he rose to fame as a cast member in “Saturday Night Live,” Pete Davidson is more known for his infamous relationships nowadays than anything else. Back in May of 2018, he began dating pop star Ariana Grande, whom he met two years prior when Grande was the guest host for SNL.
A month later, they were engaged, and fans were expecting a massive celebrity wedding. But, perhaps not surprisingly, they broke up in October of 2018. As Grande put it, “It was way too much too soon.” The pop star went on to marry real estate agent Dalton Gomez, and Davidson decided he would date any celebrity that would have him.
Ruby Rose and Catherine McNeil
Ruby Rose and Catherine McNeil's love story was one for the books. The two Australian beauties first crossed paths in their hometown of Melbourne and felt an instant connection. They started dating and, after a blissful period together, Ruby popped the question in 2010, and Catherine happily accepted.
However, as often happens in life with busy, high-profile celebrities, circumstances changed, and the couple decided to go their separate ways before exchanging vows. Ruby went on to date several models, actresses, and even Phoebe Dahl (famous writer Roald Dahl’s granddaughter), over the years. Catherine later got married to Miles Plumlee, an American professional basketball player.
Lady Gaga and Taylor Kinney
Lady Gaga and actor Taylor Kinney seemed like the perfect match when they began dating in 2011. Kinney even appeared in Gaga's music video for "You and I," and the couple were so crazy about each other that, after four years of dating, they got engaged on Valentine's Day in 2015.
However, just a few months later, they announced that they had called off their engagement. Gaga later revealed that her busy schedule and Kinney's desire to start a family were factors in their split. Despite their breakup, the two have remained friendly and even attended a Chicago Cubs game together in 2017.
Nick Cannon and Selita Ebanks
Back in the spring of 2007, famous actor, rapper, and comedian Nick Cannon decided to go all out and propose to Victoria's Secret model Selita Ebanks right smack in the middle of Times Square. He popped the question on a giant jumbotron for everyone to see, and of course, Ebanks said “yes.”
But it seems the big gesture wasn’t enough to keep them together, because just five months later, they decided to call it quits. Why? Because they needed to focus on their careers, apparently. Shortly after, Cannon went on to marry the legendary diva Mariah Carey, but, unfortunately, they ended up divorcing after eight years. As for Ebanks, she decided to put all her energy into her modeling career and make it her top priority.
Christina Ricci and Owen Benjamin
The “Addams Family” star Christina Ricci is happily married to hair stylist Mark Hampton since 2021, and the two share a daughter. But this wasn’t Ricci’s first engagement rodeo, because back in 2009, she had every intention of walking down the aisle with comedian Owen Benjamin. The actress met Benjamin in 2008, on the set of the film “All’s Faire in Love,” a romantic comedy that ended up being a flop.
However, their relationship blossomed, and by March 2009, the couple announced their engagement. Unfortunately, a few months after, Owen was celebrating his birthday and he and Christina got into a big fight, which was seemingly intense enough to cause them to break up. Luckily, they remain good friends to this day.
Jeffrey Dean Morgan and Mary-Louise Parker
“Weeds” star Mary-Louise Parker and Jeffrey Dean Morgan had a romance that blossomed on set in 2006. Two years later, in 2008, Morgan proposed to Parker, but by the time spring came around, their engagement was up in smoke. Parker, who already had a son from a previous relationship, decided to grow her family further by adopting a baby girl from Ethiopia in 2007.
Perhaps Morgan wasn't ready for kids yet? Anyway, Morgan later went on to have a relationship with actress and businesswoman Hilarie Burton, and in 2010, they welcomed a son into the family. Eight years later, a daughter came along. Seems like a happy ending for everyone.
Kate Hudson and Matt Bellamy
In a cosmic encounter, actress Kate Hudson found love with musician Matt Bellamy, frontman of the band Muse. The couple met in 2010 and got engaged a year later. A few months into their engagement, they had a gorgeous son named Bingham. But even that wasn’t enough to get them to walk down the aisle.
In 2014, they called it off, but things seem to have turned out quite well for both. Kate Hudson has since found happiness with her current partner, musician Danny Fujikawa, with whom she has a daughter. As for Matt Bellamy, he tied the knot with model Elle Evans in 2019.
Kyle MacLachlan and Linda Evangelista
Once upon a photo shoot in 1992, the charming Kyle MacLachlan, star of the cult classic show “Twin Peaks,” crossed paths with stunning model Linda Evangelista. They began dating and seemed to have six years of romantic bliss and finally got engaged. Unfortunately, the engagement didn’t last for long. MacLachlan, ever the witty gentleman, confessed, "I couldn't see the point of tying the knot when the relationship was heading nowhere."
At least he was honest about it. Nowadays, MacLachlan is married to TV producer Desiree Gruber, whom he met filming “Sex and the City” and had a kid with. Evangelista went on to conquer the world of fashion and have a son with one of her partners – who happens to be Francois-Henri Pinault, one of the world’s wealthiest businessmen.
Jennifer Love Hewitt and Ross McCall
When Jennifer Love Hewitt met Scottish actor Ross McCall on the set of “Ghost Whisperer,” it was love at first sight. They started dating in late 2005, and two years later, on a Hawaiian vacation, McCall popped the question. But unfortunately, the wedding bells never rang, and their plans got canceled the following year.
They kept the reasons for their breakup private, with even their nearest and dearest not knowing what happened exactly. Thankfully, they both moved on — Hewitt went on to marry fellow actor Brian Hallisay in 2013, and the couple has three adorable kiddos to show for it. McCall went on to land several high-profile gigs on British TV.
Melissa Rycroft and Jason Mesnick
Melissa Rycroft and Jason Mesnick's whirlwind romance on "The Bachelor" had fans on the edge of their seats. After accepting Mesnick's proposal in the season finale, Rycroft was on cloud nine, ready to plan the wedding of her dreams. But alas, the fairy tale took a detour. Mesnick, known for his change of heart, blindsided the Dallas Cowboys cheerleader on the "After the Final Rose" special, confessing that he still had feelings for the runner-up.
Ouch! Rycroft handled the breakup like a champ, gracefully moving on to find her happily ever after. She married Tye Strickland in 2009 and they now have three beautiful children. As for Mesnick, he followed his heart and married Molly Malaney, the very woman he had second thoughts about.
Britney Spears and Jason Trawick
After her debut album “…Baby One More Time” came out in 1999, Britney Spears became one of the highest-selling artists in music history. The “Princess of Pop” was known around the world, and her career was about to get even bigger. Almost twenty years later, we finally know that this pop star’s life has been no picnic, and her love life wasn’t great either.
Somewhere in between her teenage stardom and her infamous conservatorship, Spears started dating her talent agent, Jason Trawick, in 2009. By 2010, they were engaged, but two years later, they called it quits. According to Britney, they remain good friends to this day.
Nick Young and Iggy Azalea
Famous American former basketball player Nick Young was another celebrity that never made it down the aisle – and with none other than world-famous rapper Iggy Azalea. Their story started back in 2013 after they met at a mutual friend’s pool party, and Azalea reportedly “hated him” at first!
A year later, Young posted a Tweet saying that he had a huge crush on the rapper, and so she agreed to go out on a date with him, to Target. Fast forward a year later, and the two got engaged in 2015. But the bliss didn’t last for long – Azalea called off the wedding less than a year later after she found Young being unfaithful on their home security video, while she was away on tour.
Demi Lovato and Max Ehrich
Singer and actress Demi Lovato might appear to be head over heels for her current boyfriend – Canadian singer Jordan Lutes. But there was a time when this famous pop star was in love — and even engaged — to someone else. In 2020, Lovato started dating actor Max Ehrich, and apparently, things were going very well because Ehrich popped the question just four months later.
They were engaged for two short months before Lovato called off the wedding, supposedly because her family and friends didn’t approve of the relationship. Ehrich later said the singer had broken up with him via social media, and of course Lovato denies it. Whatever happened, it seems these two are definitely better off apart.
Kanye West and Alexis Phifer
Kanye West's marriage to Kim Kardashian, his public outbursts, and his involvement with Julia Fox have all been headline stealers. But one thing that seems to have faded out of public consciousness is that West almost tied the knot with someone else before becoming a part of the Kardashian family.
Back in 2002, West started dating fashion designer Alexis Phifer, and they had a happy relationship for six whole years. In 2006, they got engaged after the rapper proposed while on holiday in Italy. Unfortunately, the relationship started to go downhill after West’s mother Donda, whom the rapper was very close with, passed away in 2007. In 2008, they finally called it quits but apparently remained good friends.
Karamo Brown and Ian Jordan
In a fabulous twist of fate, "Queer Eye" star Karamo Brown found love with actor and TV director Ian Jordan. This dynamic duo met back in 2010, and after eight years of dating, finally got engaged in 2018, making us all swoon with their heartfelt Instagram posts.
However, life had different plans for these lovebirds, and they announced their split in 2020. But fear not, dear fans, for Karamo has moved on to greener pastures. He is currently raising two sons and dating the handsome photographer, Carlos Medel. Karamo has told Page Six that he is ready to marry Medel, but no official statement is out yet.
Drew Barrymore and Leland Hayward III
Hollywood star Drew Barrymore has always been known as a rebel child. Ever since she was a kid and starred in the famous classic “E.T.,” her life has been in the spotlight. Barrymore has had quite an exciting life – from obtaining juvenile emancipation at the young age of 14 and living in her own apartment at 15 to getting engaged when she was only 16 years old!
Barrymore met and fell for Leland Hayward III, grandson of the legendary Hollywood agent and producer of the 40s and 50s. Hayward and Barrymore got engaged in 1990, but after a few months, they called it quits in the summer of 1991. The “Charlie’s Angels” star went on to get married three times, which all ended in divorce.
Taraji P. Henson and Kelvin Hayden
“Empire” star Taraji P. Henson met Kelvin Hayden through a mutual friend and instantly clicked. By 2016, they had started dating, and their relationship really took off, becoming one of the industry's hottest couples. In 2018, Kelvin popped the question, and Taraji excitedly accepted, sending fans into a frenzy of anticipation.
However, in 2020, they decided to part ways before walking down the aisle. As Taraji explained in a later interview, “when one person is taking on the weight of the entire relationship, it's never going to work." Amen to that! Taraji has an incredible career under her belt and Hayden retired with honors from a long NFL career.
Jennifer Morrison and Jesse Spencer
Shortly after the release of the hit TV show “House,” two of its co-stars fell for each other. Jennifer Morrison and Jesse Spencer played colleagues on the show but were in a serious relationship offscreen. So serious, in fact, that Spencer popped the question in 2006, while they were visiting the Eiffel Tower in Paris.
The actor later confessed it had taken him six months to work up the courage to pop the question. Unfortunately, by August 2007, the actors announced their official split but made sure to mention that they remained close and planned to keep on working together. And thank god for that, because we needed to see how “House” ended!
Raquel Leviss and James Kennedy
Raquel Leviss and James Kennedy's relationship had its fair share of drama on the reality TV stage. The couple met in the wild world of “Vanderpump Rules,” where Leviss quickly caught Kennedy's eye. After a tumultuous on-again, off-again romance that lasted five years, they finally got engaged in 2021. However, just seven months after Kennedy proposed, the engagement came to an abrupt halt.
Rumor has it that Kennedy's commitment issues contributed to the breakup. Leviss is currently enjoying the single life and focusing on her budding career, while Kennedy has found solace in the arms of his music career, spinning records and staying clear of relationship turbulence. Cheers to new beginnings and drama-free playlists!