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16 Of The Longest Celebrity Engagements

According to some dating rules, there’s a certain period people should wait before they get engaged. Then there’s a specific amount of time couples should wait before getting hitched. Of course, rules were made to be broken. And it’s celebrities in particular who are known for bucking tradition on the relationship front and writing their own rules.

There are some celebrities who seem to get engaged (and sometimes married) basically two seconds after meeting each other. Similarly, there are celebs who have engagements that last weeks, if not days. On the opposite end of the spectrum are the celebrities who are engaged for-ev-er. You wonder what the holdup is. Are they planning a really big wedding? Are they not that into each other anymore? Or, are they just too lazy to plan a wedding? Just when you think that they’re never going to make it to the altar, a lot of them actually do. Take a gander at 16 celebrity couples with the longest engagements.

16. Brad Pitt and Angelina Jolie, 2 years

We’ll start with the shortest of the long celebrity engagements on our list. You’re probably very familiar with how sparks flew for Brad Pitt and Angelina Jolie when they filmed Mr. and Mrs. Smith in 2004. In 2005, Brad announced he was separating from then-wife Jennifer Aniston. Multiple births and adoptions later, Brangelina became engaged in 2012. The engagement lasted for two years before they tied the knot in 2014 with all of their kids in attendance. Despite being together for years, things didn’t work out and Angelina filed for divorce in 2016.

15. Maggie Gyllenhaal and Peter Sarsgaard, 3 years

Maggie Gyllenhaal and Peter Sarsgaard are one of the more low-key couples in Hollywood so it’s understandable if you don’t know everything about their relationship. The pair starred together in God’s Hands in 2002 and got together around the same time. In 2006, they announced their engagement and that they were expecting. Daughter Ramona was born that same year. The pair eventually tied the knot in Italy in 2009. In 2012, they welcomed a second daughter, Gloria Ray.

14. Kate Hudson and Matthew Bellamy, 3 years

Kate Hudson began dating Muse musician Matthew Bellamy in 2010. Their engagement announcement came in 2011. The same year, they welcomed a son named Bingham. This is a case where a long engagement did not lead to a wedding. In December 2014, the pair confirmed that they had decided to call off their engagement, but that they would continue to co-parent their son together amicably.

13. Dax Shepard and Kristen Bell, 3 years

Kristen Bell and Dax Shepard are one of the cutest and funniest and most romantic couples in Hollywood, but were you aware that they had a pretty long engagement? The pair met in 2007 and were on and off for a bit before they got engaged in 2010. But, they made it clear they wouldn’t get married until gay marriage was legal in California. It happened on June 26, 2013. After the ruling to rescind Proposition 8, Kristen re-proposed to Dax and they wed four months after the law change, at the end of 2013 in a courthouse ceremony. From the OG proposal, that makes a three-year engagement.

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12. Jennifer Aniston and Justin Theroux, 3 years

The split of Brad Pitt and Jennifer Aniston was well documented to say the least, but the early days of her relationship with Justin Theroux were kept more on the DL. The pair started dating in 2011 and were engaged in 2012. It was a fast engagement, but it would be three years before they became husband and wife in 2015. Unfortunately you know how this one ends. They announced their split at the start of 2018.

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11. Jessica Simpson and Eric Johnson, 3.5 years

Forget about Jessica Simpson‘s old relationship with Nick Lachey. We’re focusing on her current S/O Eric Johnson. The singer and fashion designer began dating the former NFL player in mid-2010. Before the year was up, they were engaged. The relationship slowed down a bit because the pair welcomed daughter Maxwell in 2012, followed by son Archie in 2013. In July 2014, the pair wed, meaning their engagement lasted just under four years.

10. Megan Fox and Brian Austin Green, 4 years

The timing here is up for debate with rumors that Megan Fox and Brian Austin Green got engaged, split up, and got engaged again. But, they’ve countered that saying there was just one engagement despite the speculation. What we know is that pair met in 2004 and began dating shortly after. It was reported that they became engaged in 2006, but rumors swirled any wedding plans were called off in 2009. There seemed to be a period of being on-and-off until Brian reportedly proposed again in 2010. (Both have previously spoke out alluding to it being the same engagement.) That same year they did wed. They welcomed their first child in 2012 and now have a total of three kiddos.

9. Brooke Burke and David Charvet, 5 years

Former Dancing with the Stars host Brooke Burke and David Charvet had a romantic connection on vacation, worked on their friendship, then eventually got together. In 2006, they got engaged. It would be five years (and two kids) later before they would get married in 2011 in Italy. Sadly, the pair filed for divorce in 2018 after being married for seven years. Yeah, 2018’s a rough year in celebrity couple history.

8. Carmelo Anthony and La La Vazquez, 5 years

Former MTV VJ La La Vazquez (now Anthony) began dating Carmelo Anthony in 2003. They were engaged on Christmas Day in 2004. In 2007, baby made three with Kiyan Carmelo coming into the world. It would be another three years before La La and Carmelo tied the knot in 2010, meaning their engagement lasted five years. Their relationship hasn’t been without scandals, with fidelity rumors on both sides, but they are still together.

7. Amy Adams and Darren Le Gallo, 6 years

You might not know Amy Adams‘s partner Darren Le Gallo, but you probably know the actress has been very busy, which could possibly explain the long engagement (and dating period). They pair began dating in 2001. In 2008, Darren popped the question. The pair welcomed daughter Aviana Olea in 2010. Finally in 2015, they tied the knot after being together for 14 years and being engaged for six years. If you can make it that long, it’s probably going to last forever!

6. Isla Fisher and Sacha Baron Cohen, 6 years

Sacha Baron Cohen is definitely known for his gags, and his S/O Isla Fisher is known for being a seriously funny lady. When it comes to their relationship, it seems that they were very serious. The pair reportedly met in 2002 at a party in Australia. By 2004, they were engaged. There was clearly no rush to make it to down the aisle. In 2007, they welcomed their first daughter, Olive. In 2010, they did finally get married in a ceremony with just six people in Paris. Their second daughter, Elula Lottie Miriam, was born five months after they made things official. They welcomed a son in 2015.

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5. Miley Cyrus and Liam Hemsworth, 6 years minus the split

There are a few different twists and turns in Miley Cyrus and Liam Hemsworth‘s relationship with some wondering whether they’re married, engaged or something else right now. Let’s look at the facts: They began dating after starring in The Last Song together in 2009. There were a few years of being on and off before they confirmed their engagement in 2012. After breakup rumors swirled, they announced their split in 2013 and both seemed to move on. Miley went through her infamous twerking phase. In 2016, reconciliation rumors hit tabloids before they made things Instagram and red carpet-official. The two alluded to the engagement being back on and Miley beginning to sport her engagement ring again. So, taking it from the OG engagement, they’ve been engaged approximately six years minus a few for their long-time split.

4. Rachel Bilson and Hayden Christensen, 7 years

Rachel Bilson and Hayden Christensen were a cute couple who stayed out of the limelight. So, you might learn something new about their relationship now. They met while filming the 2007 film Jumper and were reportedly engaged in 2008. There must have been trouble in paradise because the engagement was called off in 2010. The couple reunited the same year. They welcomed daughter Briar Rose in 2014, but split in 2017, after 10 years together and 7 years being engaged, if we count it from the OG proposal. (We do.)

3. Jennifer Hudson and David Otunga, 9 years

The early days of Jennifer Hudson and David Otunga‘s romance seemed like a bit of a whirlwind. They met in 2008 and were engaged in less than a year. Shortly after, they welcomed son David Otunga Jr. When previously asked about wedding plans, J-Hud would frequently say she was in no rush to get married. Unfortunately, this story doesn’t have a happy ending. After being engaged for nine years, the pair broke up in November 2017. With the news, it was reported that the singer was granted a protective order for alleged domestic abuse. In January 2018 it was reported David wouldn’t be charged.

2. Alessandra Ambrosio and Jamie Mazur, 10 years

Supermodel Alessandra Ambrosio and Jamie Mazur began dating in 2005. He popped the question in 2008. They welcomed daughter Anja Louise in 2008 and son Noah Phoenix in 2012. Alas, the pair announced they were splitting up in March 2018 after 10 years together. Just one of the many engaged celebrity couples who never actually made it down the aisle. Tragic.

1. Oprah Winfrey and Stedman Graham, 26 years and counting

Did you know that Oprah Winfrey is actually engaged? She began dating partner Stedman Graham back in 1986 and got engaged in 1992, which was the same year her show launched. If there were wedding plans, they never happened and they decided to postpone marriage. The mogul told Vogue in 2017, “What I realized is I don’t want to be married.” Ring or no ring, certificate or no certificate, they are one of the longest lasting Hollywood couples that prove you can find love if you’re famous.

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