1. Oprah Winfrey & Stedman Graham
This list couldn’t start with any other couple than Oprah Winfrey and Stedman Graham – officially the longest engagement in Hollywood. The pair got engaged in 1993 but couldn’t settle on a wedding date due their respective busy schedules, and remained that way ever since. 25 years later, and counting, the couple are still engaged.
2. Miley Cyrus & Liam Hemsworth
It hasn’t been the smoothest ride for this pair, but despite it all, they’re still going strong this far. Miley Cyrus and Liam Hemsworth got engaged in 2012 but called it quits a year later, rekindled their romance in 2016 and got engaged once again. The couple have no immediate plans to marry though – so excluding the year they spent apart, they’ve been engaged for three years and counting.
3. Kristen Bell & Dax Shepard
Actors Kristen Bell and Dax Shepard got engaged in 2009, but announced that they would wait until the state of California legalised same-sex marriage to tie the knot themselves. They stuck to their word and got hitched in 2013 after a four year engagement.
4. Sacha Baron Cohen & Isla Fisher
Actors Sacha Baron Cohen and Isla Fisher tied the knot in 2010 after a six year engagement. Isla converted her faith to marry her future-husband, and the couple married three years later in Paris and went on to have three children together.
5. Amy Adams & Darren Le Gallo
This couple waited seven years to tie the knot after getting engaged in 2008. Amy Adams and Darren Le Gallo were in no rush to head down the aisle, as the actress herself stated, and got married in 2015 in California. In an interview with The Times, Amy said she feels “a stronger sense of family, a bigger sense of permanence” since tying the knot.
6. Jennifer Anniston & Justin Theroux
The only couple on this list that didn’t last, Jennifer Anniston and Justin Theroux were engaged in 2012 but waited until 2015 to tie the knot, which they did at a small and private ceremony. Sadly, the couple announced in 2017 that they were parting ways after just 2 years of marriage.
7. Olivia Wilde & Jason Sudeikis
Olivia Wilde and Jason Sudeikis started dating in 2011 and got engaged two years later, but appear to have put marriage plans on hold, choosing to expand their family instead. The couple have two children together, Otis and Daisy, and have now been engaged for five years.
8. Megan Fox & Brian Austin Green
Another pair with a long-winded engagement, Megan Fox and Brian Austin Green started dating in 2004 when the actress was just 18 years old. They got engaged two years later, but broke off their relationship in 2009. It was only a year later that these two rekindled their romance, and officially tied the knot on a Hawaiian island in 2010.