The fifth child of Jim Bob and Michelle, Jessa Duggar, was born on Nov. 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, leading Jim Bob to explain to People, “Courting is getting to know each other in a group setting, with both families spending time together and the couple setting goals to determine if they are meant to marry. In dating, couples often pair off alone, which can 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 Nov. 1, 2014. At the time of the cancellation of 19 Kids and Counting, Jessa was pregnant with their first child. TLC later aired a special about sexual abuse featuring Jill and Jessa to educate viewers on the topic. The sisters eventually became stars of their own show, Jill and Jessa: Counting On, that winter; the show later evolved into Counting On, which included other Duggar siblings as well.

During this time, Jessa and Ben welcomed son Spurgeon on Nov. 5, 2015, son Henry on Feb. 6, 2017, daughter Ivy Jane on May 28, 2019, and daughter Fern in July 2021. In February 2023, Jessa revealed that she had 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.