Jessa met Ben Seewald through their church, and their courtship began in 2013. This traditional approach to romance was a novel concept for many viewers. Pre-engagement, the Duggar children did not discuss their romantic relationships publicly. Jim Bob Duggar explained to People, “Courting is about getting to know each other in a group setting, with both families spending time together. It’s about setting goals to see if marriage is in their future. In contrast, dating often involves a couple spending time alone, which can lead to a more physical relationship.”

Ben asked for Jessa’s hand in marriage and proposed in August 2014, marking the occasion by holding her hand for the first time. The couple wed on November 1, 2014. During her first pregnancy, the reality show 19 Kids and Counting was canceled. Subsequently, TLC aired a special focusing on sexual abuse, featuring Jessa and her sister Jill. This special aimed to inform viewers about the issue. That winter, the sisters launched their own show, Jill and Jessa: Counting On, which later expanded to include other Duggar siblings and was renamed Counting On.

Jessa and Ben welcomed their first child, a son named Spurgeon, on November 5, 2015. They later had son Henry on February 6, 2017, daughter Ivy Jane on May 28, 2019, and daughter Fern in July 2021. In February 2023, Jessa revealed she had experienced a miscarriage over the 2022 holiday season. She then gave birth to their son George in December 2023.

In August 2025, Jessa announced the arrival of their son Edward.

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