‘Counting On’: A Look Back at Every One of Jana Duggar’s Failed Courtships

The love life of Counting On star Jana Duggar has become a bit of an obsession for many fans. As the only single adult daughter of Jim Bob and Michelle, Jana is 31-years-old and is still living at home with her parents. Per Jim Bob’s rules, of course.

Recently, rumors have started to swirl that Jana is courting a pilot from Nebraska named Stephen Wissman. But this isn’t the first time Jana’s been linked to a single guy who knows the Duggars. Here’s a look back at everyone of the “Cinderella Duggar’s” failed courtships.

Jana Duggar
Jana Duggar from ‘Counting On’ | TLC via YouTube

‘Counting On’ star Jana Duggar was linked to an NFL quarterback

Back in 2014, Jana was briefly linked to former NFL quarterback and professional baseball player Tim Tebow. The rumors didn’t last long, and it doesn’t appear that Jana and Tim actually met. The rumors started after a photo of Jim Bob and Michelle meeting Tim’s mom, Pam, went viral.

Fast forward to 2021, Jana is still single. While Tim just celebrated his first wedding anniversary with his wife, former Miss Universe Demi-Leigh Nel-Peters.

What about ‘Bringing Up Bates’ star Lawson Bates?

For years, fans of fundamentalist-reality TV have shipped Jana and Bringing Up Bates star Lawson Bates. Like the Duggars, the Bates are a super-religious, conservative family who has 19 children. The Duggars and the Bates have also been friends for years.

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While it seems that Jana and Lawson were a match made in Heaven, it was never meant to be. Lawson has occasionally liked some of Jana’s Instagram posts, but that’s about all there is to it. In February 2021, Lawson introduced his girlfriend Tiffany Espensen to his 256K Instagram followers.

Jana Duggar has been linked to three different Duggar family friends

While Tebow and Bates are the most notable men that Jana has been linked to, there are three others who at one time appeared to be Duggar family friends. After the rumors about Jana and Lawson died down, it was reported that Jana was courting longtime family friend, Jonathan Hartono. He quickly shut the rumor down.

In 2016, photos surfaced of Jana hanging out with family friend Jacob Wilson a few different times. This briefly sparked courting rumors. But they ended just as quickly as they started. Then, there was the infamous Caleb Williams.

It’s not clear if anything ever went on between Jana and Caleb. But, he definitely stands out among Jana’s potential suitors for a number of reasons.

Caleb Williams got himself into some serious trouble

At first, there appeared to be some truth to the rumors that something was going on between Jana and Caleb Williams. He spent a lot of time with the Duggar family, and occasionally popped up in family photos. He also attended the same church.

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Caleb wasn’t just spending time with Jana, either. He was also spotted spending time with her dad, so he appeared to be Jim Bob-approved. But what brought the courting rumors to an abrupt end were the statutory rape charges against Caleb. He eventually pled guilty to aggravated criminal sexual abuse and was sentenced to 62 days in jail and 18 months probation. He eventually moved out of Arkansas.

Is Jana Duggar dating Stephen Wissmann?

There’s been another rumor that’s been pretty persistent when it comes to Jana’s love life — her friendship with Laura DeMasie. While some fans have speculated that Laura and Jana are much more than besties, Jana has denied these accusations.

Fans haven’t heard anything from Jana yet, though, about Nebraska pilot Stephen Wissmann. The rumors about a possible courtship have heated up in recent weeks after a photo surfaced of Jana at the Wissmann house in Nebraska during Christmas. Nothing has been confirmed yet. But fans are hoping for a courtship announcement soon.

Counting On is currently on hiatus. Fans can watch classic episodes on Hulu.