Engagements are so sweet.

There’s something so heartwarming about a person getting down on one knee and asking to spend the rest of their life with their love. At least, engagements should be a lifetime commitment. Unfortunately, that’s not always how things work out, especially if you’re a celebrity with all the world focused on your personal life.

Keep scrolling for 35 celebrity engagements that never came to be.

(via @xclassy90s)

Ariana Grande & Pete Davidson

(via @arianagrande)

This is perhaps one of the most dramatic broken engagements in recent history. In May 2018, singer Ariana Grande and SNL comedian Pete Davidson began dating weeks after they both ended long-term relationships. Just a few short weeks into their relationship, the couple was engaged. For a few months, both Ariana and Pete were totally obsessed with each other, getting tattoos in honor of the other person and posting constantly on social media. But within five months, the couple called it quits. Since then, they’ve often shaded each other publicly, though both have moved on to new relationships.

Emma Roberts & Evan Peters

(American Horror Story via FX)

In 2012, Emma Roberts and Evan Peters starred together in a film called Adult World. Soon after filming ended, the pair started dating. However, their romance was anything but smooth sailing. In July 2013, Emma was arrested after a domestic violence incident in a Montreal hotel. She and Evan confirmed that the incident was just a misunderstanding, and Evan proposed to Emma just five months later. But in June 2015, the pair called things off. They got back together and broke up a few more times throughout the following years before finally separating for good in 2019.

Jennifer Lopez & Ben Affleck

(via @ginaway1)

Much like Brad Pitt and Jennifer Aniston, Jennifer Lopez and Ben Affleck were an adored couple in Hollywood. Graced with the moniker Bennifer, this couple first met while filming Gigli in 2002. They immediately fell for each other and got engaged after doing a few more professional projects together, including Jersey Girl. Unfortunately, things weren’t meant to be, and the pair never made it down the aisle. They broke up in 2014, breaking fans’ hearts around the world.

Robert Pattinson & FKA Twigs

(via @fka_and_robert)

Robert Pattinson generally tries to keep things pretty quiet in his personal life, and his relationship with FKA Twigs was no exception. The pair dated for three years and apparently got engaged, though most people knew nothing about their relationship until they called things off in 2017. Sources later claimed that Rob proposed to the singer in early 2015 after just six months of dating. Rob later said they were “kind of” engaged, but confirmed rumors of their split himself.

Alanis Morissette & Ryan Reynolds

(via @90s80s70s60s50s)

Before he was the funny guy with the most perfect family, Ryan Reynolds was engaged to musical legend Alanis Morissette. The pair met at Drew Barrymore’s birthday party in 2002, and their relationship took off. After two years of dating, the couple got engaged, but they never managed to set a wedding date. Then, in 2007, they ended their engagement for good. Thankfully, Reynolds moved on to his perfect wife, Blake Lively.

Zayn Malik & Perrie Edwards

(via @zaynster_perrie)

Although Zayn Malik is known for his on-again, off-again relationship with Gigi Hadid, that romance wasn’t the first big relationship of Zayn’s life. Before Gigi, Zayn dated Little Mix band member Perrie Edwards. The pair began dating in 2012 and got engaged in 2013. In 2015, however, the couple called it quits. Now, Zayn is expecting a baby with Gigi. It seems that things worked out for the best.

Cameron Diaz & Jared Leto

(via @90ssclassy)

The “it” couple of the early 2000s, Cameron Diaz and Jared Leto dated from 1999 to 2003. In 2000, the pair got engaged. Unfortunately, it wasn’t meant to be. While they continued to date for three more years, Cameron and Jared never made it down the aisle. While Cameron went on to marry Benji Madden, Jared is still single to this day.

Brad Pitt & Gwyneth Paltrow

(via @90s.daily)

Before Brad and Angie or even Brad and Jen, Brad Pitt fell for Goop founder Gwyneth Paltrow. The pair dated from 1994 to 1997 and had a very serious and very public relationship. When Brad proposed, Gwyneth initially accepted. However, she later called it off because she didn’t feel ready for marriage.

Hayden Christensen & Rachel Bilson

(Jumper via 20th Century Fox)

In 2008, Hayden Christensen and Rachel Bilson met on the set of Jumper. In December of that same year, they were engaged. But by August 2010, the couple quietly ended their engagement. In December 2010, however, they were suddenly back together. They didn’t get married, but they welcomed a daughter in 2014 and stayed together until 2017. At that point, they officially went their separate ways, though they continue to co-parent their child.

Rob Kardashian & Blac Chyna

(via @_rob_blacchyna)

After just 10 weeks of dating, Rob Kardashian proposed to Blac Chyna in 2016. Just a month later, the couple announced that they were expecting their first child. The pair stayed together despite a lot of drama with Rob’s family and welcomed their daughter in November of 2016. But just a year after they started dating, Rob and Chyna broke up, sparking the beginning of a long battle between the two, which was fully documented on social media. Chyna eventually got a restraining order against her ex-fiancé, and the couple continued to fight their battles in court as Rob struggled to see his child. It’s safe to say this couple is one who should have never gotten together.

Iggy Azalea & Nick Young

(via @thenewclassic)

Australian rapper Iggy Azalea started seeing Nick Young after he posted about her on his Instagram for Woman Crush Wednesday. In 2015, Nick proposed to Iggy in front of all their friends and family with a custom-made ring. However, things weren’t as perfect as they seemed. The wedding was put off because of Nick and Iggy’s intense work schedules, but things fell apart when a video emerged that seemed to show Nick cheating on Iggy. While the couple tried to work through things for a few months, they eventually called off their engagement in June 2016.

Sandra Bullock & Tate Donavan

(Love Potion No. 9 via 20th Century Fox)

Sandra Bullock starred in the 1992 movie Love Potion No. 9 alongside Tate Donovan, but their chemistry wasn’t limited to the big screen. These stars started dating after filming ended, and eventually got engaged. However, they broke up after three years together and went their separate ways. Bullock did make it down the aisle a few years later when she married Jesse James, though the couple is now divorced.

Jennifer Aniston & Tate Donovan

(via @90ssclassy)

Sandra Bullock wasn’t the only star to get hot and heavy with Tate Donovan. Tate starred on Friends alongside Jennifer Aniston as one of Rachel’s many love interests. Interestingly enough, Tate and Jennifer had a history long before his appearance on the show. After dating for three years, Tate proposed to Jennifer in 1998. Despite their long relationship, the engagement only lasted a year. After they broke things off, Tate was cast to play Joshua on the show. That must have been awkward.

Kerry Washington & David Moscow

(via StereoCulture Society)

Before she made a name for herself in the entertainment industry starring as Olivia Pope in Scandal, Kerry Washington appeared in Hollywood on the arm of actor David Moscow. The pair were engaged from 2004 to 2007, but never made real plans for their wedding. Kerry later admitted that she never even felt like picking out a dress. The couple later realized that they loved each other deeply, but that the relationship was harder than it should have been. They called things off and Kerry went on to marry Nnamdi Asomugha.

Kim Kardashian & Reggie Bush

(via @accessonline)

While Kim Kardashian did have an incredibly short marriage to Kris Humphries, that wasn’t the first time she accepted a proposal. While an engagement was never confirmed, fans concluded that Kim and Reggie Bush must have been planning a wedding at some point due to a wedding registry, confirmed wedding date and Kim sporting a ring on that finger. However, Reggie and Kim couldn’t make their relationship work amid Kim constantly filming TV shows and Reggie’s constant partying. Their relationship eventually came to an end, and neither one ever confirmed whether they were expecting wedding bells in their future.

Sean Penn & Charlize Theron

(via @charlizetheronfan)

After a 16-year marriage to Robin Wright, Sean Penn moved on to actress Charlize Theron after his divorce. He began dating Charlize in December 2013 and proposed to her just a year into the relationship. But after 18 months together and only six months into their engagement, the pair called it quits. Although there were rumors of some dramatic ending, Charlize insisted that their relationship just didn’t work out—simple as that.

Nikki Bella & John Cena

(via @johncena_nikkibella_nena)

After John Cena divorced his wife Elizabeth Huberdeau in 2012, he started dating fellow WWE star Nikki Bella. They dated for many years before John finally got down on one knee in 2017. By April 2018, however, the pair announced that they called off their wedding. They then got back together a few months later, only to call off their wedding again. This time, the decision seemed to stick.

Mariah Carey & James Packer

(via @mariah_storys)

In January 2016, Mariah Carey got engaged to James Packer. At that point, the couple had only been dating for seven months. However, they seemed to realize their mistake pretty quickly. While on a vacation in Greece later that year, the couple decided to go their separate ways.

Johnny Depp & Sherilyn Fenn

(via @90ssclassy)

Johnny Depp is basically the king of broken engagements. His first failed betrothal was to actress Sherilyn Fenn, whom he met in 1985 on the set of a student film. They dated on and off for three years before calling it quits for good. Despite their ups and downs, they were engaged for a short time in the midst of the three-year relationship. Fenn later went on to marry musician Toulouse Holliday in 1994.

Johnny Depp & Jennifer Grey

(via @deppstagram)

After Sherilyn Fenn, Johnny Depp moved on to date another actress, Jennifer Grey. He got engaged to the Dirty Dancing star in 1989 after her relationship with Matthew Broderick came to an end. Alas, it still wasn’t the right fit for Johnny. He and Jennifer broke up a year later, ending their engagement.

Johnny Depp & Winona Ryder

(via @myjohnnypie)

Shortly after the end of his relationship with Jennifer Grey, Johnny Depp met Winona Ryder at a movie premiere in 1990. After dating for just five months, the pair got engaged. At the time, Johnny often spoke about how important Winona was to him. He even got a tattoo on his arm that read, “Winona Forever.” After three years, however, the relationship came to an end. That was, fortunately, Johnny’s last public engagement for a while.

Kiefer Sutherland & Julia Roberts

(via @stylingitvintage)

Julia Roberts made a splash in Hollywood early on in her career. At just 23 years old, after starring in popular films like Pretty Woman, Steel Magnolias, and Sleeping With the Enemy, Julia met 24-year-old Kiefer Sutherland. The pair moved in together in 1990, and just a year later Julia was spotted with a ring on that finger. However, their relationship was plagued with rumors of constant issues. Just three days before Julia was meant to walk down the aisle, their wedding was canceled.

Alyssa Milano & Scott Wolf

(via Old Loves/Pinterest)

Alyssa Milano is known for having a long dating history. Heck, even she makes jokes about it. Some of her former partners include Justin Timberlake and David Arquette. But in 1993, Alyssa truly fell for Scott Wolf. The pair met on the set of Double Dragon, and their relationship quickly went from 0 to 100. They moved in together after two months and got engaged just two months later. However, their relationship didn’t even last a year, and the engagement was broken off.

Demi Moore & Emilio Estevez

(via @80sradical)

Before Demi and Ashton, superstar Demi Moore was engaged to fellow actor Emilio Estevez. Demi and Emilio starred together in St. Elmo’s Fire before getting engaged in 1985. Despite the volatile nature of their relationship, the two got as far as setting a wedding date for December 1986. However, they called it quits before they could make it down the aisle. Since they were on and off for most of their romance, it was probably a smart decision to simply walk away.

Drew Barrymore & Leland Hayward

(via Pinterest)

After Drew Barrymore made a splash in Hollywood by starring in E.T., everyone wanted to know more about her personal life. At just 14 years old, Drew was granted juvenile emancipation, allowing her to live and work without the input of her parents. At just 16, she accepted an engagement with 24-year-old Leland Hayward. Thankfully, Drew must have realized that she was too young to make a lifelong commitment because she called off the engagement just a year later.

Drew Barrymore & Jamie Walters

(via Pinterest)

While Drew Barrymore didn’t go through with her engagement to Leland Hayward, she obviously didn’t learn her lesson. A year after that relationship ended, Drew was engaged again, this time to Jamie Walters. The pair lived together for about a year, but broke up in 1993.

Sheryl Crow & Lance Armstrong

(via @sherylcrow and @lancearmstrong)

In 2003, famous cyclist Lance Armstrong finalized his divorce from his wife. That same year, Lance started dating singer Sheryl Crow. In September 2005, the couple announced their engagement to the world. But their happiness was short-lived. Just a few short months later in February 2006, they broke up. It was a shock to everyone that things could have changed so quickly.

Jennifer Love Hewitt & Rose McCall

(via @jenniferlovehewitt)

While starring on Ghost Whisperer, Jennifer Love Hewitt met and fell for Scottish actor and guest star Ross McCall. The pair began dating in 2005 and stayed together for two years before Ross proposed to Jennifer in Hawaii. Just a year later, however, the couple canceled their wedding plans. Jennifer went on to marry actor Brian Hallisay, and today shares two children with him.

Sienna Miller & Jude Law

(via @because_of_rain)

After Jude Law’s divorce from his first wife, he met and started dating Sienna Miller. He later proposed to her on Christmas Day in 2004. However, things quickly went south. In July 2005, Jude released a public apology for engaging in an affair with his children’s nanny. In November of that same year, the relationship between Sienna and Jude came to an end. They later reunited in 2009, only to call things off once again in 2011.

Jeffrey Dean Morgan & Mary-Louise Parker

(via Dreamstime)

Before he played Negan on The Walking Dead, Jeffrey Dean Morgan was engaged to Mary-Louise Parker. The pair met on the set of Weeds and started their on-again, off-again relationship in December 2006. They got engaged in February 2008, but they called things off in April. Jeffrey then went on to date and have a child with Hilarie Burton of One Tree Hill.

Robin Wright & Ben Foster

(via @robingwright)

In 2010, Robin Wright got divorced from husband Sean Penn. The House of Cards actress soon began dating Ben Foster. They got engaged in 2014, but called things off just a few months later. They then reconciled and re-established their engagement in January 2015, but again things only lasted a few months. In August of that year, the pair called things off for good.

Lenny Kravitz & Nicole Kidman

(via Pinterest)

Lenny Kravitz and Nicole Kidman were very quiet about their relationship. They started dating all the way back in 2000, but no one knew they got engaged until Nicole mentioned it in a 2017 interview. She nonchalantly brought up the engagement while discussing her role opposite Zoe Kravitz in Big Little Lies. She later said the relationship just wasn’t the right fit, and that she and Lenny weren’t really ready for marriage at the time.

Nick Cannon & Selita Ebanks

(via @selitaebanks)

After just six months of dating Victoria’s Secret model Selita Ebanks, Nick Cannon proposed. But five months after he elaborately popped the question using a Times Square jumbotron, Selita and Nick realized they had more than a few fundamental differences. The couple parted ways in October 2007, at first claiming they were just taking a break to focus on their careers. However, it soon became clear that their split wasn’t temporary.

Paris Hilton & Paris Latsis

(via @2000sblondeglam)

Paris Hilton likes herself so much she nearly married a man with the same name! In May 2005, Hilton accepted a proposal from a Greek shipping heir named Paris Latsis. The engagement happened just eight months into their relationship, and Paris was able to choose her ideal ring from fifteen options. Sadly, Paris-squared ended their engagement just four months later.

Katie Holmes & Chris Klein

(via @iamchrisklein and @katieholmes212)

Before Katie Holmes married Tom Cruise, she had a pretty serious relationship with fellow actor Chris Klein. The pair began dating in 2000 and got engaged in 2003. Although they stayed together for a while after their engagement, they eventually ended their relationship in 2005. Shortly after, Katie Holmes started dating Tom Cruise, whom she eventually married in 2006.

35 Celebrity Engagements That Never Came to Be