Who Has Jana Duggar Courted? Her Dating History

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.

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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.

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Jana and Stephen Wissmann

The eldest Duggar daughter was rumored to be courting the handsome Nebraska pilot in early 2021. The two appeared in a 2020 holiday photo with his family, and the Duggars and Wissmanns took a joint family trip to Waco, Texas. But the two never confirmed they were officially courting, and whatever the pair had together ran its course by September 2021.

Jana and Lawson Bates

In August 2019, Jana hinted her Mr. Right might be “riding in on a green turtle instead of a white horse,” shortly after Lawson posted a photo with a turtle. One month before that, fans noticed that the Bringing Up Bates star and pilot had been traveling to Arkansas quite often. He even wrote a sweet comment to Jana when she joined Instagram in 2019. At the time, fans pointed out that the Duggar kids usually aren’t allowed to get social media until they are courting.

When Jana shared this Instagram photo in August 2020, Lawson wrote in the comments, “Post objective/instruction unclear: pls explain further,” with a laughing face emoji and a black heart. Fans hoped the somewhat flirty comment meant that the pair were going to make things official, but no courting arrangement resulted. Lawson is now engaged to actress Tiffany Espensen.

Jana and Caleb Williams

Fans thought Jana had found a potential suitor in September 2017, when the Duggars posted a Facebook photo at dinner with family friend Caleb. He was quick to shoot down rumors that he was courting Jana, writing on Facebook, “Now to clear the fog and avoid any confusion: Read my lips… I am not dating Jana Duggar.”

Caleb added about the photo that showed the top of his underwear partially visible, “Over the past several months since an extremely unflattering image was posted by my friends and spread across the world faster than a viral cat video, there has been speculation regarding a relationship between myself and Jana. The extent of our relationship is purely friends and nothing more.”