Josh Duggar was the first of the 19 Duggar children to get engaged when he surprised Anna Keller with a proposal while she was out eating lunch with her parents. Jill Duggar then became the second child and first daughter to get engaged. Derick Dillard had a country singer serenade Jill for the proposal. Next, Jessa Duggar became engaged to Ben Seewald, who organized a scavenger hunt for the proposal.
Jim Bob, the Duggar father, introduced Jill to Derick Dillard after meeting him during missionary work in Nepal and sensing that he seemed like the type of man his daughter may like. The two communicated with one another over Skype and text message for several months before meeting in person. Jill claims she was in love with him before she had ever even seen him in person.
As part of Jessa's scavenger hunt proposal, she had to unlock clues by completing tasks, such as getting a hole-in-one on a golf course and gathering a dozen roses from strangers. At the end of the hunt, Ben Seewald proposed in Thorncrown Chapel.
The Duggar family believes in entering into a dating phase called a courtship prior to engagement. In April of 2015, Josiah Duggar announced he had begun courting Marjorie Jackson. However, four months later, the couple announced their decision to call off the courtship.