‘Counting On’: How Each Duggar Got Engaged

For most people, a marriage proposal is one of the biggest moments in their life – no matter if they are asking or answering the question. That’s not the case, though, for members of the Duggar family. Thanks to their extremely conservative beliefs, the Duggar siblings wait until their wedding day for their first kiss. And, this means that their proposals are all about smiles, side hugs, and TLC cameras. Let’s take a look at how each married Duggar sibling got engaged.

The Duggar family
The Duggar family | Photo by D Dipasupil/Getty Images for Extra

Josh and Anna Duggar

The oldest of 19 children, Josh Duggar was the first one in the family to pop the question. And, when he asked Anna Keller in June 2008 to be his wife, he did it in the most awkward way possible. While Anna was having dinner with her parents in a family restaurant, Josh showed up dressed in a suit and tie with balloons in hand. He then sat down next to Anna so they could have a conversation, and her parents left to give the couple some privacy.

Josh nervously told Anna that he had a question for her, and proceeded to get down on one knee while Anna had a shocked look on her face. He told her to “come here,” so she slid her way to the edge of the booth, stood up, and Josh asked her to be his wife. Anna simply said was “yes,” and then they shared a side hug.

Jill Duggar and Derick Dillard

The first few weeks of Jill Duggar and Derick Dillard’s courtship happened online because Derick was on a mission trip to Nepal. But, after he got home and spent one month with Jill, Derick took her for a romantic walk through the park. They eventually came upon a musician who was singing and playing the guitar, and it turns out, Derick had staged the whole thing.

The man sang them a special song he had written about their love story, and when the song came to an end, Derick got down on one knee and asked, “Jill Duggar, would you marry me?” In one of the greatest responses to a proposal of all time, Jill says, “Yes! Totally!” before they shared a side hug.

Jessa Duggar and Ben Seewald

A few short months after Derick and Jill got engaged, Ben Seewald got his turn to pop the question to Jessa Duggar, and he didn’t disappoint. After an epic two-day scavenger hunt that included a plane flight (piloted by Jessa’s big brother, John David), a trolley ride, and miniature golf, Jessa ended up at Thorncrown Chapel. Of course, Ben was waiting for her with a ring in hand.

“I walked in and he was standing there at the front,” Jessa said. “I could barely talk. I knew he was going to propose. I cried.”

Jessa and Ben immediately broke the rules by sharing a front hug, but they managed to avoid sharing a kiss. They also took advantage of the new privileges of engagement and held hands as they walked out of the chapel.

Joy-Anna Duggar and Austin Forsyth

During a horseback riding date on an Arkansas trail – complete with chaperones – Austin Forsyth asked Joy-Anna Duggar to be his bride. However, unlike the other Duggar siblings, TLC cameras didn’t catch this special moment.

The couple did reveal in an interview right after the proposal that everything fell into place perfectly, and they were excited that they now could hold hands.

Joseph Duggar and Kendra Caldwell

When Austin and Joy-Anna got married on May 27, 2017, they gave her brother Joseph Duggar permission to pop the question to Kendra Caldwell during their reception. Joe took the opportunity to propose in front of all their family and friends because he knew Kendra would say yes.

“I was definitely nervous going into it, but I wasn’t afraid that she was going to say no because she has said, ‘I’m just waiting on you!’” Joseph told People Magazine.

Jinger Duggar and Jeremy Vuolo

Jeremy Vuolo took Jinger Duggar (along with Jessa, Ben, and mom, Michelle) to New York City to surprise her with a proposal, but he kept his plans a secret by telling her he had arranged a photo shoot at sunset on a New York City rooftop with the Empire State Building in the background. The problem was that when they got there, it started raining.

“I’m talking to Jinger, trying to act normal, but inside I’m just saying, ‘Lord, please stop this rain,'” Jeremy revealed.

However, when it was time to pop the question, the rain stopped and a rainbow emerged. Jinger had no idea it was coming, and when Jeremy dropped to one knee she couldn’t believe what was happening. After asking if he was serious, Jinger said yes.

Josiah Duggar and Lauren Swanson

Josiah Duggar kept things low-key and simple when he proposed, but that didn’t mean there wasn’t a lot of meaning behind the location he picked. Josiah took Lauren Swanson to the same place in George where her parents got engaged.

And, at the exact same spot, Josiah dropped to one knee in front of hay bales, roses, and a picture of her mom and dad, and asked Lauren to be his wife.

She said she would love to marry him, and the newly-engaged couple shared a side hug.

John David Duggar and Abbie Grace Burnett

John David David is a pilot who has a passion for aviation, and he put that on full display when he popped the question in July 2018 to Abbie Grace Burnett. John David took Abbie Grace to an old-fashioned airplane hangar for his proposal, complete with rose petals shaped in a heart and “Abbie will you marry me” written on a marquee.

John David asked Abbie Grace if she wanted to keep flying with him, and she said she would love to.

New episodes of Counting On will return to TLC later this year.