She is the sister of Joshua Duggar, Jana Duggar, John-David Duggar, Jill Dillard, Jinger Vuolo, Joseph Duggar, Josiah Duggar, Joy-Anna Forsyth, Jedidiah Duggar, Jeremiah Duggar, Jason Duggar, James Duggar, Justin Duggar, Jackson Duggar, Johannah Duggar, Jennifer Duggar, Jordyn-Grace Duggar, and Josie Duggar.
As a child, Jessa has said she had quite a headstrong personality. According to her book, Growing Up Duggar, she especially clashed with older sister, Jana. They were forced to share a bunk bed and Jessa would repeatedly kick Jana's bed at night. Under her mother's advice, Jana gave Jessa her most prized possession - her jewelry box.
Jessa was homeschooled growing up. As she grew older, she was given the responsibility of helping her younger siblings with their schoolwork in addition to doing her own. Jessa took the test for her GED at sixteen years old.
Like most children, Jessa was assigned chores growing up, which the family called "jurisdictions". In 2009, one of Jessa's jurisdictions was managing the family's computer-based schooling system, on which she was the administrator. In 2011, Jessa's jurisdictions were organizational work, tutoring Jackson and Johannah, and preparing supper. Jessa was no longer expected to keep up with her jurisdictions after she began her courtship.
By 2001, Jessa's parents had implemented a buddy system, where each older child was paired with a younger child to take care of. Typical tasks for an older buddy included dressing, bathing, and feeding their younger buddies. By 2009, the family had switched from individual buddies to buddy teams, with each team being led by one of the oldest four daughters. Jessa's buddy team consisted of Jeremiah, Justin, and Jordyn-Grace.
Jessa began taking piano lessons from Ruth Anita Anderson, who she and her siblings referred to as "Nana", as a young child. She also took violin lessons. As an adult, Jessa has been seen playing the harp, but it is unknown when she learned to play this instrument.
In late 2009, after her sister Josie was born premature, Jessa moved with her family into the Cornish House in Little Rock, Arkansas, to be closer to the Neonatal Intensive Care Unit (NICU). Once Josie was able to leave the hospital and survive on her own, Jessa and her family returned to their home in Springdale, Arkansas.
In 2010, Jessa was an extra on the film Courageous, which was released on September 30, 2011. Although the entire family was on set, Jessa was one of the only family members to make it into the film's final cut. She was seen as an attendee of a young girl's funeral.
Jessa met Ben Seewald when he attended her family's church. Ben befriended her brothers, and as he spent more time around the family he got to know Jessa too.
On September 9, 2013, Ben asked Jessa's father, Jim Bob, for permission to court Jessa. Jim Bob gave his permission, and immediately brought Jessa into the room so Ben could ask her too. This courtship proposal, which was featured in the 19 Kids and Counting episode "Flea Market Finale", gained some national attention - being mocked on some late night talk shows and internet gossip sites for its awkwardness.
Jessa and Ben set high standards for themselves during their courtship, allowing themselves only limited physical contact. "Jessa and Ben have said that was the only contact they would have," Jessa's mother, Michelle, said of their rules, "when they initially greet each other, when he comes to visit for their first hello, they have a quick 30-second-or-less side hug and a goodbye side hug, and they agreed that would be the only contact they should have.". During their courtship Ben moved into a separate building on the Duggar property to be closer to Jessa and avoid the 3 ½ hour drive between them. Ben also worked for Jim Bob during this time doing various jobs.
Ben proposed to Jessa on August 4, 2014. The proposal included a scavenger hunt that involved both of their families.
The first step was a dinner the night before with both of their parents where they had their first date. Ben gave Jessa a present that she was not allowed to open until the next day.
The gift was a tablet with a prerecorded message on it, instructing Jessa to go to the plane hangar where her older brother, John-David, would fly her to Ben's hometown.
They arrived at mini golf, where the couple went on a double date with Jessa's parents, and Jessa must score a hole in one to get the next clue.
Jessa then had to collect a dozen roses from strangers in the park, which was specifically designed to get her out of her comfort zone.
The next clue sent them to take a trolley ride where Jessa took a quiz about her relationship with Ben. On the trolley ride, Jessa was presented with a special outfit for her to wear.
The final destination was Thorncrown Chapel, which was lit with candles and has rose petals down the aisle. Ben was at the end of the aisle and where he proposed.
Jessa and Ben's wedding took place on November 1, 2014. Jessa's maid of honor was her sister Jinger. The other bridesmaids were her sisters Jana, Jill, and Joy-Anna, future sisters-in-law Jessica, Danielle, and Michelle, and friends Amanda Query, Anna Hackel, Peyton Weiss, and Jennifer Hartono. Her brothers Joseph and Josiah were among the groomsmen. Her flower girls were her sister Jordyn-Grace and her future sister-in-law Faith.
Jessa's dress was designed by Allure Bridals and was a blush color. It was purchased at Tesori in Fayetteville, Arkansas. Notable parts of the wedding were the ice cream sundaes served at the outdoor reception, the couple's exit to the Arkansas Razorbacks fight song, and their decision to leave the sanctuary before their first kiss, which was witnessed only by a photographer.
For their honeymoon, Jessa and Ben went on a tour of Europe, including Paris, France, and Rome and Venice, Italy.
Jessa and Ben have publicly expressed a desire to adopt children on many occasions, and have looked into the possibility of fostering children as well.
On April 21, 2015, the Seewalds announced that they were pregnant with their first child, due on November 1, 2015, their first wedding anniversary. After 27 hours of labor, Jessa gave birth to son, Spurgeon Elliot, on November 5, 2015, in her home. Shortly after, Jessa was rushed to the hospital to be treated for blood loss. This birth is featured on the Counting On episode "Counting One More".
On August 23, 2016, the Seewalds announced their second pregnancy, with a due date in February. Their second son, Henry Wilberforce, was born on February 6, 2017. The second labor went much faster than the first and there were no complications. This birth was featured on the Counting On episode "A New Baby".
On January 9, 2019, they announced that they are expecting their third child, with a due date in late spring. Their first daughter, Ivy Jane, was born on May 26, 2019. This birth was featured on the Counting On episode "A Surprise Delivery".
The couple suffered a miscarriage in 2020, but chose not to publicly speak about it at that time. They mentioned it while announcing their fourth child, calling the child a "rainbow baby".
Jessa and her family go on a yearly mission trip to El Salvador the week after Christmas. Jessa also often does missionary-type work in her local community.
On May 19, 2015, InTouch Weekly published a redacted copy of a police report dated December 7, 2006. The report revealed that Jessa's oldest brother, Joshua, had molested five underaged girls, including four of his sisters, in 2002 and 2003. In an interview filmed on May 31, 2015, Jessa named herself as one of the previously unnamed victims. Jessa was fourteen years old at the time of the police interview and ten/eleven years old at the time that the molestations were occurring. During the television interview, which aired on The Kelly Files on June 5, 2015, Jessa said that she was unaware that the molestations had occurred. "I was shocked, like okay this is strange," Jessa stated, "I didn't know, I didn't understand this is what happened." Jessa also strongly defended her brother:
"Well I think in the case of what Josh did, it was very wrong. I'm not going to justify anything that he did or say it was ok, not permissible, but I do want to speak up in his defense against people who are calling him a child molester or a pedophile or a rapist, some people are saying. I'm like that is so overboard and a lie really, I mean people get mad at me for saying that but I can say this because I was one of the victims. So I can speak out and I can say this and set the record straight here. Like in Josh's case, he was a boy, a young boy in puberty and a little too curious about girls. And that got him into to some trouble. And he made some bad choices, but really the extent of it was mild, inappropriate touching, on fully clothed victims, most of it while girls were sleeping."
On May 19, 2017, Jessa and three of her sisters sued InTouch Weekly, Springdale, Arkansas, and Washington County, Arkansas, for breach of privacy. The four women claim that they were promised confidentiality when speaking to investigators in 2006.
She was a bridesmaid at her friend Amara Query's wedding to Joshua Hulin on September 16, 2016.