A Complete Timeline of Josh and Anna Duggar’s Marriage

Josh Duggar will be spending the next decade behind bars. The father of seven was convicted of receiving and possessing child pornography in December 2021 and has since been transferred to a federal prison in Texas to serve his sentence. His wife, Anna Duggar, has supported him throughout his legal troubles. While 2021 was certainly a horrible year for the ultra-conservative Christian couple, it’s hardly the first scandal Josh and Anna Duggar have weathered. Continue reading for a complete timeline of the couple’s turbulent marriage. 

Josh and Anna Duggar became engaged in 2008 

In 2008, Josh proposed to Anna on her 20th birthday. While the couple insisted that they had courted for two years before their engagement, Duggar family followers don’t believe that to be the case. A family insider told Radar that parents, Jim Bob Duggar and Mike Keller, largely arranged Josh and Anna’s engagement. 

Anna Duggar and Josh Duggar
Anna Duggar and Josh Duggar | Kris Connor/Getty Images

The couple’s engagement came just five years after Josh was briefly removed from the Duggar family home for molesting his sisters. The engagement was not Josh’s first relationship. The troubled used car salesman was previously involved with Kayleigh Holt, the daughter of close family friends. The relationship ended after Josh was caught sexually abusing his siblings. Kayleigh’s mother, Bobye Holt outlined what happened during her testimony at Josh Duggar’s trial.  

Josh and Anna married in September 2008. The following year they welcomed their first child, Mackynzie Duggar. In 2011, Anna gave birth to the couple’s second child, Michael Duggar. 

In 2013, Josh and Anna moved to Washington D.C. 

Josh and Anna decided to make a big move in 2013. Josh accepted a job with Family Research Council, a conservative lobbying group. TLC documented the couple’s move on 19 Kids and Counting

A close-up of Josh Duggar of the Duggar family's face while he's speaking at a conference
Josh Duggar speaks during the 42nd annual Conservative Political Action Conference (CPAC) | Kris Connor/Getty Images

During their time in Washington D.C., the family welcomed another child. Marcus Anthony Duggar was born in June 2013. Josh stepped down from his position after the first of several scandals broke. He retreated back to Arkansas. 

In 2015, Josh admitted to molesting several of his sisters and cheating on his wife 

Josh’s very first scandal broke in 2015. In Touch obtained police reports that outlined sexual abuse that occurred in the Duggar family home before they landed their TLC specials and shows. According to the reports, Josh molested four of his sisters in addition to a family friend multiple times. 

Josh stepped down from his position with Family Research Council amid the scandal. Several months later, the disgraced reality TV star also admitted to cheating on his wife when a data breach revealed he was using Ashley Madison to find extramarital affair partners. Josh also used OkCupid to find sexual partners. 

Anna Duggar took to national television to discuss her feelings about Josh’s betrayal while he traveled to a religious rehabilitation program. During the scandals, Anna was pregnant with the couple’s fourth child, Meredith Duggar. She was born in July 2015.

After Josh’s release, the family returned to Arkansas to live with the Duggar family. In 2017 they welcomed their first child, Mason Duggar. The family lived in their own home 20 minutes from the Duggar family compound before selling it in the summer of 2019. They moved into a converted warehouse on the Duggar family property and lived there until Josh’s arrest. 

In 2019, the Department of Homeland Security raided Josh’s car lot 

In November 2019, the Department of Homeland Security raided Josh Duggar’s car lot. The Duggar family initially denied the raid had happened, and Anna continued to post to Instagram as if nothing was amiss. The couple’s sixth child, Maryella Duggar, was born just days after the raid. Josh was arrested two years later. Josh’s arrest wasn’t the only thing that happened in April 2021. The couple announced they were expecting their seventh child together one week before the arrest. Anna went silent on Instagram the following day.  

Josh Duggar's 2021 mugshot. Josh Duggar's sentencing was held on May 25, 2022
Josh Duggar | Washington County Sheriff’s Office via Getty Images

Madisyn Lily Duggar was born in October 2021, just weeks before Josh’s trial began. Anna announced the birth via Instagram before going dark on the platform again. The child’s name certainly gave Duggar family followers pause. The choice of Madisyn, considering Josh’s previous indiscretions, certainly felt strange. 

Josh’s 2021 conviction ensures he’ll be away from his family for more than a decade 

While Josh was originally arrested in April 2021, he was released on bond to await trial. While on bond, he was allowed to see his wife and children but could not live in their home. Instead, he spent the months leading up to his trial residing at the home of a chaperone handpicked by his father, Jim Bob Duggar. 

Once convicted of his crimes, Josh was transferred to a county detention center to await sentencing. On May 25, Federal Judge Timothy L. Brooks sentenced Josh to 151 months in jail. He was transferred to FCI Seagoville in late June. Anna Duggar was on hand for the sentencing. She left the courthouse in a hurry. 

While Anna spent the months after Josh’s arrest and trial out of the spotlight, she resurfaced on Instagram in late June and was on the move. She traveled to Texas around the time Josh was transferred to his federal prison. While it is unclear where Anna plans to live long-term, she’s got plenty of time to decide. According to the Federal Bureau of Prisons, Josh won’t be eligible for release until August 2032. She does not appear to be interested in divorce. 

RELATED: Josh Duggar’s Trial: Could Anna Duggar Move to Be Closer to Josh Duggar?