Longest Celebrity Engagements: Michelle Yeoh, Olivia Wilde More
When we think of proposals, we often assume that a wedding is right around the corner. After all, most getting-down-on-one-knee moments come with the question “Will you marry me?” at the end. But, as many couples around the world can attest to, life can sometimes get in the way of actually walking down the aisle. Plus, wedding planning can take years too!
Some of our favorite current and former celebrity couples, for example, took their sweet time as fiancés and showed no rush in tying the knot. And while that meant that some couples split before ever marrying, like Olivia Wilde and Jason Sudeikis or Alessandra Ambrosio and Jamie Mazur, many couples just took years to “make it official.”
To find out what other stars were engaged for years, and why they decided to wait, scroll below!
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Oprah Winfrey & Stedman Graham
In one of the longest engagements Hollywood has ever seen, Oprah Winfrey and Stedman Graham, who got engaged back in 1992, have yet to walk down the aisle, per Vogue.
According to Winfrey, however, their engagement status is what works for them. “The only time I brought it up was when I said to Stedman, ‘What would have happened if we had actually gotten married?’ And the answer is: ‘We wouldn’t be together,'” she told Vogue. “We would not have stayed together, because marriage requires a different way of being in this world. His interpretation of what it means to be a husband and what it would mean for me to be a wife would have been pretty traditional, and I would not have been able to fit into that.”
Michelle Yeoh & Jean Todt
In addition to winning her first Oscar in 2023, Michelle Yeoh also married her longtime partner Jean Todt after 19 years together as fiancés.
“We met in Shanghai on 4th June 2004,” their wedding program began, below a throwback picture of the two. “On 26th July 2004, J.T proposed to marry M.Y and she said YES.”
“Today after 6992 days on 27th July 2023 in Geneva, surrounded by loving family and friends, we are so happy to celebrate this special moment together!”
Celebrating the occasion on Instagram, the newlyweds radiated happiness. “19 years and YES!! we are married!!” Yeoh wrote in the caption. “Thk to our ‘families’ who love us for all these years. We love you and here’s to many more to come.”
Jamie Mazur & Alessandra Ambrosio
After not walking down the aisle during their 10 years as fiancés, supermodel Alessandra Ambrosio and Jamie Mazur called it quits in 2018.
Prior to their split, Ambrosio explained their lack of pressure to become husband and wife. “If I have been engaged to him for eight years, then it’s not my priority,” she told Cosmopolitan, per Daily Mail. “I have a lot of things going on, and I haven’t got married because I’m so busy. I’ll think about that when I have time off.”
Mazur and Ambrosio are co-parents to son Noah, 11, and daughter Anja, 15.
Amy Adams & Darren Le Gallo
Amy Adams and Darren Le Gallo were engaged for a total of seven years before walking down the aisle. “I’ve been really busy, and I feel like a horrible fiancée that I haven’t gotten swept up in the whole idea of a wedding,” Adams told Allure in 2009, per People. “But I just haven’t.”
The pair, who became fiancés in 2008, ended up tying the knot in 2015. Their only daughter, Aviana Olea Le Gallo, is now 14 years old.
Olivia Wilde & Jason Sudeikis
While Olivia Wilde and Jason Sudeikis’ breakup took over headlines from 2020 up until 2022, many might not know the two were engaged through most of their relationship. The pair, who met in 2011, got engaged in 2013 but never made it down the aisle.
During their seven-year engagement, Wilde and Sudeikis welcomed their son Otis, 10, and their daughter Daisy, 7.
In 2020, however, the pair called it quits. “It’s been amicable and they’ve transitioned into a great co-parenting routine,” a source said of their split to People. “The children are the priority and the heart of the family’s relationship.”
Sacha Baron Cohen & Isla Fisher
Sacha Baron Cohen and Isla Fisher, who announced their breakup in April 2024, were engaged for a total of six years before tying the knot. After becoming fiancés in 2004, Fisher converted to Judaism and welcomed their first child, Olive, in 2007. In 2010, they finally walked down the aisle.
Since then, the pair welcomed their daughter Elula in late 2010 and their first son, Montgomery, in 2015.
Sadly, the pair called it quits in late 2023. “After a long tennis match lasting over 20 years, we are finally putting our racquets down,” Fisher wrote on Instagram Stories at the time. “In 2023 we jointly filed to end our marriage.”
Jordan Rodgers & JoJo Fletcher
While finding love in The Bachelorette meant that Jordan Rodgers and JoJo Fletcher’s love story was on a fast track, the two took their time to plan their wedding. After getting engaged in Fletcher’s season finale in 2016, the pair planned for a 2020 wedding only to postpone it due to the COVID-19 pandemic. Two years later, in 2022, they finally walked down the aisle.
“It was the most perfect day,” she gushed to Entertainment Tonight after their nuptials. “I’m so happy we waited it out and it was truly the best day of my life.”
Carmelo & La La Anthony
Much like Fletcher and Rodgers, Carmelo and La La Anthony also waited six years after their proposal to walk down the aisle. The pair officially became fiancés in 2004 and welcomed their son, Kiyan, 16, in 2007. Three years later, they walked down the aisle and became husband and wife.
Sadly, the pair announced their split in 2017. The pair later reconciled but, in 2021, she filed for divorce citing “irreconcilable differences.”
“I’m never getting married again,” she said in an appearance at The Breakfast Club in 2022, per Entertainment Tonight. “It’s one of those things in life that I feel like I could check it off. Like, ‘OK, I did that.’ Maybe people want to say they’ve experienced that. I’ve experienced it and I know the good and the bad that happened to me so it’s not something I want to experience again. I can have an incredible relationship with somebody and not be married.”
Katy Perry & Orlando Bloom
Much like many other couples in this list, Katy Perry and Orlando Bloom focused on expanding their family before walking down the aisle. The pair, who have been engaged since 2019, welcomed their first daughter, Daisy Dove, in August 2020.
“One step at a time,” the “Teenage Dream” singer said of planning their nuptials in an interview with KISS Breakfast With Tom & Daisy in 2019, per Cosmopolitan. “[We’re] definitely trying to lay the good emotional foundation for the lifetime of commitment, which is, like, a big deal, you know?”
Eric Johnson & Jessica Simpson
Jessica Simpson and Eric Johnson will be celebrating their 10th wedding anniversary soon, but the pair took their time saying “I do.” After getting engaged the same year they met in 2010, their other priorities, including welcoming their first baby, Maxwell, in 2012, and their second, son Ace Knute, in 2013, took precedence.
Johnson and Simpson eventually tied the knot in 2014. Since then, they’ve also welcomed daughter Birdie Mae in March 2019.
Dax Shepard & Kristen Bell
In one of the most honorable reasons to wait for marriage, Dax Shepard and Kristen Bell waited until same-sex marriage was legalized to tie the knot. The pair, who confirmed their engagement at the 2010 Grammy Awards, only walked down the aisle in 2013.
“The reason we’re not rushing to get married is because I don’t feel appropriate taking advantage of a right that’s denied to my best friends,” Bell told the Advocate in 2012. “That’s why we’ve been so hesitant. Dax and I have talked about it a lot, and this issue is very important to both of us. We’re just standing up for what we believe in. Period.”
Since saying their “I do’s,” Bell and Shepard welcomed kids Lincoln, 10, and Delta, 8.
