Top 10 Celebs You Forgot Were Engaged But Never Got Married

These two made quite the formidable duo. Sheryl Crow has sold over 50 million albums and won nine Grammys, and Lance Armstrong set a world record with seven straight Tour de France wins between 1999 and 2005. Armstrong was divorced from his wife Kristin in 2003 and quickly began dating Crow after meeting her at a charity event. The two were engaged in September of 2005 - just two months after Armstrong “won” his seventh Tour de France - and they appeared together on an episode of “Saturday Night Live” to commemorate the event. Unfortunately, the pair officially split the following February, the wedding never went forward as planned and Armstrong was later stripped of his wins following a doping scandal.

Shortly after dating her “O.C.” co-star Adam Brody, Rachel Bilson entered into a ten-year on-again-off-again relationship with “Star Wars’” Hayden Christensen. The two co-starred in the movie “Jumper” and kept their budding relationship a secret from prying eyes. Bilson was spotted with a ring that looked like it was for an engagement in February of 2009, but the two refused to publicly confirm anything. It wasn’t until August 2010 that the engagement was formally acknowledged by Bilson’s representative. Unfortunately, it was only to inform her fans that it had been called off. And while the couple would later reunite and have a daughter together, they never married and went their separate ways in 2017.

Both actors, Jeffrey Dean Morgan and Mary-Louise Parker ended long-term relationships in 2003. Morgan divorced Anya Longwell, his wife of eleven years, and Parker was left by Billy Crudup when she was seven months pregnant with their child. The two had been together since 1996, and Crudup left Parker to be with Claire Danes. The two now-single celebrities met each other while filming “Weeds” and quickly fell in love. They proudly announced their engagement in February of 2008, but it was tragically short-lived, ending just two months later. Morgan started dating his current wife, Hilarie Burton, the following year.

British-American fashion designer Phoebe Dahl collaborated with Ruby Rose to design clothing for Dahl’s company, Faircloth & Supply. At the time, Rose was known for her modeling and television hosting, but she would soon garner even greater popularity by starring as Stella Carlin in “Orange Is the New Black”. The two dated for nearly two years, becoming engaged in 2014. Unfortunately, conflicting work commitments often kept them apart, and the distance soon proved too great a weight to carry. The couple officially broke up in December of 2015 and began dating other people. Rose saw The Veronicas’ Jess Origliasso, and Dahl a DJ named Tatiana de Leon.

#6: Demi Moore & Emilio Estevez

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Nowadays, Demi Moore is well known for her celebrity marriages to Bruce Willis and Ashton Kutcher. But in the mid ‘80s, she was engaged to Charlie Sheen’s brother and Brat Pack member Emilio Estevez. The two met while filming “St. Elmo’s Fire”, a coming-of-age film that grossed almost $40 million in the summer of 1985. They periodically dated for two years and eventually became engaged, with the wedding set for December of ‘86. Unfortunately, they cancelled the wedding owing to a busy work schedule. Things never really worked out, and the two ultimately ended their engagement and went their separate ways. Estevez went on to marry Paula Abdul, and Moore Bruce Willis.

These two were living the good life in the late ‘90s. Katie Holmes was starring in “Dawson’s Creek”, and Chris Klein had a leading role in “American Pie”, perhaps the most popular and influential teen comedy of the decade. The two began dating each other in 2000 and were engaged by the 2003 holiday season. Unfortunately, the couple permanently split before they could marry in March of 2005. The very next month, Holmes famously began dating Tom Cruise. It was a relationship that would generate much publicity, controversy, and even personal trouble for Holmes, as she found herself caught in the world of Scientology.

These two made an adorable Canadian couple. Ottawa’s Alanis Morissette and Vancouver’s Ryan Reynolds met each other while attending a birthday party for Drew Barrymore in 2002. The two instantly hit it off and quickly began dating. By June 2004, they were officially engaged. They remained as such for the next two and a half years, but both the wedding and the relationship ended in February of 2007. The grief that Morissette was feeling inspired her to make the album Flavors of Entanglement, while Reynolds quickly began dating his future first wife, Scarlett Johansson.

#3: Nicole Kidman & Lenny Kravitz

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These two celebrities are very private people. So private, in fact, that no one even knew they were engaged! They began dating each other in 2003, shortly after Kravitz’s engagement to model Adriana Lima and after Kidman famously split from Tom Cruise. In 2007, long after they had broken up, Kidman revealed to Vanity Fair that she had been secretly engaged to a popular celebrity. Said celebrity was later revealed to be Kravitz. Exactly ten years after the bombshell Vanity Fair reveal, Kidman began working with Kravitz’s daughter on HBO’s “Big Little Lies”.

#2: Julia Roberts & Kiefer Sutherland

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These two young stars were all the rage by 1990. Sutherland had starred in some popular films, like “The Lost Boys” and “Stand by Me”, and Roberts became the biggest name in Hollywood with the record-shattering “Pretty Woman”. The movie grossed over $450 million, and to this day remains the most popular romantic comedy of all time in terms of domestic tickets sold. The two met each other while filming “Flatliners” and were scheduled to marry in mid-June of 1991. However, Roberts called off the wedding with just three days to go, reportedly fearing that Sutherland was having an affair with a go-go dancer. On the day of the wedding, Roberts traveled to Ireland with Sutherland’s “Lost Boys” co-star Jason Patric.

These two megacelebrities have been the subjects of very pronounced and public relationships. Paltrow was married to Coldplay’s Chris Martin from 2003 to 2016, and Pitt has been married to both Jennifer Aniston and Angelina Jolie. The two dated between 1994 and 1997, and were actually engaged to each other, co-starring in 1995’s “Seven,” in which they play a married couple. Following a very public engagement, the anticipated wedding was cancelled and the loving celebrities went their separate ways. Paltrow blamed herself, telling Diane Sawyer, “My kind of internal stuff really tripped up that whole relationship and I felt really responsible.” However, an anonymous source told People that Pitt was “commitment-shy”.