Duggar Proposals: See the Romantic Moments the Stars Got Engaged

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Josh and Anna

Josh Duggar flew down to Florida so that he could propose to Anna Duggar (née Keller) on her birthday. Though he respected that her father wanted her to be at least 20 when she got engaged, the oldest Duggar son couldn’t wait a single day longer than he had to.

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Josh and Anna

While she and her parents were out to dinner, he surprised them with balloons. And when her parents stepped away to give them a little privacy, he revealed that he had a second surprise for his future bride.

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Josh and Anna

Anna was so shocked that it took a while for her to finally accept his proposal. Once she had, they shared a chaste side hug as hidden cameras captured the whole thing.

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John David Duggar Proposes to Abbie Grace Burnett 1

John David and Abbie

When you know, you know! In July 2018, just one month after John-David Duggar announced his courtship with Abbie, the reality star got down on one knee. The romantic day started off with a meal the couple shared with two of their (many, many) sisters.

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John David Duggar Proposes to Abbie Grace Burnett 2

John David and Abbie

John is the family pilot, so when it came time for the big question, he decided to center his proposal around planes, opting for an old-fashioned hangar as the backdrop. Both sisters whipped out their phones to capture the special moment on camera.

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John David Duggar Proposes to Abbie Grace Burnett 3

John David and Abbie

The pilot decorated the hangar with a giant puddle of rose petals arranged into the shape of a heart and a marquee with the question, “Abbie, will you marry me?” hanging in the background. How stunning is that?

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Derick Dillard Proposes to Jill Duggar 1

Jill and Derick

Derick pulled out all the stops to woo Jill on March 29, 2014, taking her on a romantic stroll in a park. While there, they came across a musician he had secretly arranged to perform a song for them. If the lyrics sounded just a little too familiar to be a coincidence, it might be because the future groom and musician co-wrote the tune about the Duggar love story specifically.

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Derick Dillard Proposes to Jill Duggar 2

Jill and Derick

Once the music wrapped, Derick proposed with a white gold band and a round, .63-carat solitaire diamond from Israel! Jill looked beyond excited, quickly responding, “Yes, totally!”

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Derick Dillard Proposes to Jill Duggar 3

Jill and Derick

Months earlier, when Jill and her family picked Derick up from the airport after he flew back from Nepal, the two shared a scandalous front hug. Luckily, this time around, they managed to keep their hands (mostly) to themselves.

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Jessa and Ben

When it was Ben Seewald‘s turn, he knocked it out of the park. On August 15, 2014, he led Jessa Seewald (née Duggar) on an epic scavenger hunt that lasted two days. John David even flew her to Hot Springs, Arkansas, Ben’s hometown, where she stopped by a miniature golf course, took a trolley ride and rode a train before reaching Thorncrown Chapel.

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Jessa and Ben

Once she got there, Ben was waiting with a diamond ring. “I walked in and he was standing there at the front,” Jessa told People. “I could barely talk. I knew he was going to propose. I cried.”

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Jessa and Ben

Despite the fact that they had a chaperone watching over them — peep Jessa’s little sister keeping an eye on things from the very last pew — the two still lost their control for a second when they shared a front hug instead of a side hug.

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Jessa and Ben

They quickly remembered themselves, but as they walked down the aisle of the church, they realized they could finally hold hands instead.

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Jeremy Vuolo Proposes to Jinger Duggar 1

Jinger and Jeremy

Jeremy Vuolo decided on his own unique approach, bringing Jinger Duggar to her favorite city in the world. When they stepped out onto a New York City rooftop during sunset, she thought they were just going to take a few romantic photos.

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Jeremy Vuolo Proposes to Jinger Duggar 2

Jinger and Jeremy

Though Jeremy was convinced that Jinger was going to catch on when she heard the nearby musicians playing a song that was special to them, she seemed legitimately shocked when he dropped down to one knee.

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Jeremy Vuolo Proposes to Jinger Duggar 3

Jinger and Jeremy

The surprise was clear on her face — and it took forever for her to finally say yes. She seemed completely out of breath as she asked, “Are you serious?” and finally admitted, “Babe, I can’t believe it.”

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Jeremy Vuolo Proposes to Jinger Duggar 4

Jinger and Jeremy

The two were so caught up in the moment that they even shared a pretty passionate seeming embrace as the sky turned pink and purple behind them.

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Joseph Duggar Proposes to Kendra Caldwell 1

Joe and Kendra

Joe and Kendra started courting in March 2017, and Joseph figured out the perfect time and place to pop the question: Austin and Joy-Anna’s wedding on May 27! After getting permission from the couple, the bride even stepped up to help out. When it came time to toss her bouquet, she delivered it directly to her future sister-in-law.

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Joseph Duggar Proposes to Kendra Caldwell 2

Joe and Kendra

Kendra was shocked and honored — but she didn’t seem to get what was happening until Joseph got down on one knee in front of all of the wedding guest attendees.

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Joseph Duggar Proposes to Kendra Caldwell 3

Joe and Kendra

Though she later admitted she couldn’t actually hear him ask her to marry him, she immediately answered yes. “I was definitely nervous going into it, but I wasn’t afraid that she was going to say no, because she [had] said, ‘I’m just waiting on you!'” Joseph told People.

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Josiah Duggar Proposes to Lauren Swanson 1

Josiah and Lauren

Josiah decided on a more low-key approach when asking Lauren to be his wife in March 2018, but his idea was so sweet and sentimental. He went to the exact same place where her dad proposed to her mom in Georgia years ago.

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Josiah Duggar Proposes to Lauren Swanson 2

Josiah and Lauren

The couple went for a romantic walk with her father as their chaperone before he brought her over to a decorated stack of hay bales. There, he dropped down to one knee in the grass to ask Lauren for her hand.

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Josiah Duggar Proposes to Lauren Swanson 3

Josiah and Lauren

Though the bride-to-be didn’t seem particularly caught off guard by the question, she did appear to get legitimately choked up after they sealed the deal with a side hug. “I feel like the most blessed guy on Earth … Lauren said YES!” Josiah captioned a selfie he shared from the moment on social media.

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Austin Forsyth Proposes to Joy-Anna Duggar 1

Joy and Austin

Joy-Anna and Austin got engaged on March 3, 2017. The reality star took his bride-to-be and some of her siblings horseback riding, and when they took a break to stretch their legs, he blindfolded her and led her to a beautiful overlook.

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Austin Forsyth Proposes to Joy-Anna Duggar 2

Joy and Austin

However, the blindfold may not have been the best choice. Even though she opened her eyes to find him kneeling with a ring in front of her, the first words out of her mouth were, “Is my hair all messed up?”

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Austin Forsyth Proposes to Joy-Anna Duggar 3

Joy and Austin

The reality of the situation quickly set in when he asked her to spend the rest of their lives together. “Austin made this day really, really special,” she told Us Weekly. He added, “I knew we were ready for this next step because everything fell into place. … Everything was just perfect.”