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The Duggar family is best known now for Josh Duggar’s legal troubles. Years before federal marshals arrested the former reality TV star, the Duggar family was seen as a mostly wholesome Christian family. Their TLC shows, 19 Kids and Counting and Counting On, certainly tried to paint the family in a positive light. Despite the show’s best efforts, Duggar family critics spent years calling out the family’s strange behavior, noting there was something not quite right about the supersized clan. To be fair, there were plenty of odd moments during the run of both reality TV shows. We’ve collected three of the most peculiar Duggar family episodes. 

Jessa Duggar holding up a peace sign while surrounded by the Duggar family
Jessa Duggar of the Duggar family | D Dipasupil/Getty Images for Extra

Jim Bob and Michelle Duggar double date with Jessa and Ben Seewald 

Jessa Seewald was the first of her sisters to enter a courtship, although she was not the first to tie the knot. Much of her romance was captured on 19 Kids and Counting before the series was canceled after molestation allegations came to light. While most of her courtship felt robotic and rigid, it was still typical enough of young love. Jessa and Ben’s double date with Jim Bob and Michelle Duggar, however, remains one of the family’s oddest episodes. 

In the cringeworthy episode, Jessa and Ben agree to go on a double date with Jim Bob and Michelle Duggar, who take the opportunity to discuss how the couple plans to navigate physical affection during their courtship. When the duo explained that they’ve opted to only engage in side hugs for the time being, Jim Bob, and Michelle were pleased. It didn’t stop the married couple from showing the youngsters what they were missing by essentially spooning during a mini-golf game. How awkward. 

The episode is no longer available for streaming. 

Josh and Anna Duggar’s engagement episode leaves viewers with ‘the ick’ 

Josh Duggar is serving a decade behind bars for possessing and receiving child pornography. Several years before the arrest, he admitted to molesting several of his sisters and a family friend. Given the nature of his crimes, it should come as no surprise that any episode he’s involved in feels creepy. Still, none are as uncomfortable as the 19 Kids and Counting episode that featured Josh and Anna Duggar’s engagement. 

Anna Duggar sits for an interview following Josh Duggar's molestation and cheating scandal
Anna Duggar | TLC/YouTube

In the episode, Josh flies to Florida to surprise Anna Duggar by proposing to her on her 20th birthday. Shocked and reluctant to even leave the restaurant booth she is seated in, Anna eventually agrees to marry Josh, and they share a side hug to seal the deal. Duggar family critics note just how unsettled Anna appeared during the proposal. 

For years, there has been speculation that the duo didn’t officially court. Rather, some family followers believe their marriage was negotiated between Jim Bob Duggar and Michael Keller. Critics have used the engagement episode as proof. 

The episode is no longer available on any streaming platform. 

The Duggar kids attend an odd marriage retreat during one episode of ‘Counting On’ 

Something about placing several siblings and their spouses together in a house for a “marriage retreat” hits a little weird. In 2019, several Duggar couples embarked on a marriage retreat to strengthen their relationships. During a series of increasingly odd bonding activities, it became abundantly clear which teams could work together and which were just ill-suited to a partnership.

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A Timeline of Josh Duggar’s Arrest and Trial

The episode made Duggar family followers look at Josiah Duggar and Lauren Swanson’s relationship differently, that’s for sure. The duo became so frustrated with each other during some activities that they were forced to finish them solo. The passive-aggressive nature of their dynamic had a lot of viewers feeling uneasy. 

The episode, “Marriage Bootcamp,” is the seventh episode in the show’s 10th season. It is still available for streaming on discovery+.