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

Jessa met Ben through church, and he began courting her in 2013—this traditional approach to romance was a new concept for many viewers. The couple refrained from discussing their relationships before engagement, prompting Jim Bob to explain 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 and that sometimes leads to a more physical relationship.”

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

During this time, Jessa and Ben welcomed their 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 revealed that she experienced a miscarriage during the 2022 holiday season. She gave birth to son George in December 2023.

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