Jana Duggar’s Courting History: Who Has the Family’s Single, Eldest Daughter Dated?

When it comes to the Duggar family children, the courting process usually begins in their late teens to early twenties, followed in quick succession by an engagement and marriage. But as the eldest sister in a family of 19 kids, Jana Duggar hasn’t found The One yet, despite several attempts at courting.

Fans thought Jana might have found Mr. Right when she appeared to be courting pilot Stephen Wissmann in late 2020. A Tumblr user posted a photo of Jana and Stephen seated together during his family’s Christmas celebration. The snapshot was posted to the Wissmann family blog, but was later deleted.

It was noted by fans that it was the first time that Jana spent the holidays away from her family in Arkansas, as his roots are in Nebraska. Like Jana, Stephen is devoutly religious.

“Stephen is a man of many talents,” his family’s website reads in Stephen’s description. “He enjoys being a pilot, assistant manager of Wissmann Enterprises, Inc., making small furniture, and being physically active through workouts and sports. He is gifted in initiating conversations that encourage and challenge, and he has a heart for ministry. He directs a lot of our music arrangements, plays mandolin and guitar, and sings lead and bass.”

Jana and Stephen’s relatives appeared to get along, as the Duggar family and the Wissman family apparently spent time together in Waco, Texas, posing in front of the silos near Chip and Joanna Gaines‘ Magnolia Market.

When U.K.’s The Sun reached out to Stephen about the courting rumors, he didn’t deny them but told the publication, “I’m busy with work.” Neither Jenna nor Stephen ever commented on their relationship status and whatever the pair did have seemed to have fizzled out by September 2021.

In the strict rules of the Duggar family, courting involved a couple getting to know one another, but with a number of provisions. They are always accompanied by a chaperone or are part of a group and never left alone together. There’s also no kissing or physicality involved. Holding hands is reserved for after a couple is engaged, and the first kiss occurs at the couple’s wedding.

Scroll down below to see a complete guide to Jana’s courting history.