The Longest Celebrity Engagements

Length of engagement: 2 years, the first time...

Current status: Together

Bilson and Christensen met on the set of Jumper and became engaged in 2008. Then they broke up in 2010. Then they reunited and have been together ever since—but still aren't married. They do have a daughter, now: Briar Rose, who will be two in October.

Length of engagement: Three years

Current status: Happily married

The actors began dating in late 2007 and announced their engagement in January 2010, after Bell proposed to Shepard via Twitter. They decided to delay their marriage until the state of California passes legislation legalizing same-sex marriage, which happened on June 26, 2013. The couple, who have two daughters—Lincoln, 3, and Delta, 18 months—were married just four months later.

Length of engagement: Three years

Current status: Happily married

For the longest time, it seemed Jen An would never find love again—at least, that's what the tabloids wanted us to believe. So we all breathed a sigh of relief when she began dating Theroux in May 2011. The two were engaged on August 10, 2012, and married at their Bel Air estate last August.

Length of engagement: Three years

Current status: Happily married

The actors first started dating in 2002 and in April 2006, they announced their engagement. Three years later, on May 2, 2009 the two finally tied the knot and they share two daughters, Ramona, 9, and Gloria, 4.

Length of engagement: Three years

Current status: Separated? Married? Divorcing? Who knows?

Their romantic history is a roller-coaster ride. They began dating in 2004, got engaged in 2006, but by February 2009, they broke it off. Fox and Green (that should be the name of a TV show, they could fight crime!) got back together, were engaged yet again and got hitched in June 2010. They have two sons, Noah, 3, and Bodhi, 2, but then they broke up, are maybe back together and expecting their third child.

Length of engagement: Three and a half years

Current status: Happily married

Simpson and the retired NFLer began dating in May 2010 and were engaged by November. But then wedding talk was put on hold when Simpson became pregnant with their first child. Daughter Maxwell was born on May 1, 2012, and wedding rumours began swirling—until Simpson revealed she was pregnant again. She had son Ace on June 30, 2013 and the two married a year later.

Length of engagement: Four years

Current status: Split

The pair began dating in the spring of 2010. They got engaged the following year and three months later, on July 9, 2011, they welcomed their son, Bingham, into the world. The two announced the end of their engagement, and relationship, in December 2014 but remain friendly.

Length of engagement: Five years

Current status: Happily married

The couple began dating in 2006 and quickly got engaged. After five years and two children together, they tied the knot in a surprise ceremony on August 12, 2011.

Length of engagement: Five and a half years

Current status: Happily married

The NBA star and former MTV VJ got engaged in 2004, had son Kiyan in 2007, and exchanged official vows on July 10, 2010, in a ceremony that was filmed for TV.

Length of engagement: Six years

Current status: Happily married

Their relationship has moved at a leisurely place, which was fine for both of them. They dated for 11 years, he popped the question in 2008, their daughter was born two years later and they finally tied the knot in May 2015.

Length of engagement: Six years

Current status: Happily married

The couple met in 2002 and became engaged in 2004. But it wasn’t until March 15, 2010, did they decide to wed. The two have two daughters, Olive, 9, and Elula, 5 and son Montgomery, 1.

Length of engagement: Eight years

Current status: Together

The supermodel and businessman have been together since 2005 and got engaged three years later, right around the time daughter Anja was born. They also had son Noah in 2012 but still haven't gotten hitched.

Length of engagement: Seven and a half years

Current status: Together

The singer and former WWE wrestler got engaged on Hudson's birthday, September 12, 2008, and she gave birth to her first child, son David Jr., the following year. But they have yet to make it official.

Length of engagement: 24 years

Current status: Together

The couple have been together since 1986 and got engaged in November 1992. The ceremony, however, never took place and Winfrey and Graham opted to have a spiritual union instead.

Length of engagement: ???

Current status: Happily married

To be honest, we're not sure if they were engaged, and if so, for how long. They've been together since 1983—33 years, that’s a lifetime in Tinseltown!—and share two children, Nicholas, 27, and Sophie, 23. It was during Season 6 of their reality show, Gene Simmons Family Jewels, when the longtime loves finally married on Oct. 1, 2011.