Jim Bob and Michelle’s fifth child, Jessa Duggar, was born on November 4, 1992.

Jessa met Ben through church, and he began courting her in 2013—the traditional approach to romance was a new concept for many viewers. The couple never discussed their relationships before engagement, so Jim Bob explained to People, “Courting is getting to know each other in a group setting, both families spending time together, and the couple setting goals together to determine if they are meant to marry. With dating, a couple will often pair off alone, which can sometimes lead to a more physical relationship.”

Ben asked for Jessa’s hand and proposed in August 2014—marking the moment by holding her hand for the first time. They married on November 1, 2014. Jessa was pregnant with their first child when 19 Kids and Counting was canceled, and TLC subsequently aired a special about sexual abuse featuring Jill and Jessa to further educate viewers on the subject. The sisters eventually became the stars of their own show, Jill and Jessa: Counting On, that winter; the show later evolved into Counting On, featuring other Duggar siblings as well.

Meanwhile, Jessa and Ben welcomed son Spurgeon on November 5, 2015, son Henry on February 6, 2017, daughter Ivy Jane on May 28, 2019, and daughter Fern in July 2021. In February 2023, Jessa shared that she suffered a miscarriage over the 2022 holiday season. She gave birth to son George in December 2023.

In August 2025, Jessa announced the birth of son Edward.