Joseph Duggar And Kendra Caldwell Take Big Step, Joseph Mocks Engagement Ring Excitement

Joseph Duggar and Kendra Caldwell just took a major step forward in their relationship, but Joseph hasn’t started taking the idea of marriage seriously just yet.

The Duggars recently went on a road trip that spanned at least four states, and 18-year-old Kendra Caldwell accompanied them on their trek. Jim Bob and Michelle Duggar are extremely strict when it comes to their children’s romantic relationships, so it’s a pretty big deal that they allowed the girlfriend of 22-year-old Joseph Duggar to travel with them. Kendra appears with the family in a March 31 Facebook photo that was taken outside a Skyline Chili restaurant in Ohio.

Kendra Caldwell is the girl in the plaid shirt and khaki skirt, and that’s Joseph Duggar next to her in the black T-shirt. Both of Kendra’s hands are visible in the picture, but it’s too far away to see if she’s wearing an engagement ring.

According to the Duggar Family News: Life Is Not All Pickles and Hairspray Facebook page, the Duggars were likely in Ohio to visit Michelle Duggar’s family. They also stopped at the National Museum of the United States Air Force located at Wright-Patterson Air Force Base while they were in the Buckeye State. Kendra, Joseph, James, Jennifer, and Joy-Anna posed for a photo with a female airman. Kendra has her arm around Joseph in the picture, so her engagement ring finger is hidden from view once again.

“So Kendra is now traveling with the family? The courtship must be pretty far along,” one fan wrote in response to the image.

Kendra Caldwell also appears with Joseph Duggar and his family in a March 28 photo that was taken at the Ark Encounter theme park in Williamstown, Kentucky. However, the travelers weren’t just driving across the country taking in the sights. As the Inquisitr previously reported, their final destination was an April 1 wedding in Powell, Tennessee. The Duggar family’s former tutor, Tabitha Paine, tied the knot on April Fools’ Day, and she said “yes” to a controversial groom: convicted rapist Tim Robertson.

Tabitha is the sister-in-law of Erin Bates Paine, so the other famous family of 19 was also at the wedding. Joseph Duggar hung out with his close friend Lawson Bates, and the guys got a bit goofy. Lawson pretended to be a girl showing off her engagement ring, and Joseph pretended to be excited about the bling on his friend’s finger.

“If guys acted like girls,” Lawson captioned a Twitter photo of the silly moment.


Joseph Duggar might not take engagement rings very seriously right now, but he’s already given Kendra Caldwell a ring to signify his commitment to her. As Entertainment Tonight reports, he presented Kendra with a promise ring when he asked her to enter into a courtship with him early last month.

“A promise ring signifies that I promise that I’m going to wait for you for marriage,” Joseph tells Kendra in their courtship announcement video.

Joseph and Kendra had talked for six months before they made their relationship official. They met each other through church, and Joseph says that they “hit it off really well.”

As the Ashley’s Reality Roundup reports, Kendra appears in Jinger Duggar’s wedding special. When the episode aired, viewers were not aware of that there was a love connection between Kendra and Joseph. The teen girl and her younger sister, Lauren, were introduced as friends of the Duggar family, and they were filmed helping Joseph and his siblings work on wedding decorations.

According to Kendra Caldwell, she couldn’t be happier that the world finally knows that she’s courting a Duggar.

“I’m looking forward to side-hugs and getting to do phone calls and texting and also getting to do ministry stuff out in public and for everyone to know we’re courting,” Caldwell said.

If she’s excited about simply getting to text Joseph Duggar, just imagine how much Kendra is looking forward to exchanging her promise ring for an engagement ring. She just has to hope that Joseph doesn’t mock her excited reaction when he pops the question.

[Featured Image by Duggar Family/Facebook]