On Monday’s Counting On season premiere, Duggar, 23, asked Caldwell, 19 to enter into a courtship with him after he got the blessing from her father.
“I’ve known Kendra for about five years now and we met at their church. We’ve been talking for close to six months. I guess we would call it more of a friendship stage,” Duggar explained, and added of the special day he planned for her, “Our plan is to go to the car auction and use this as a decoy so she won’t catch on to what we’re actually planning on doing.”
Duggar decided to incorporate a car auction into the itinerary because he works at a car lot and frequently attends auctions to purchase vehicles that he sells. “It’s not going to be that abnormal for me to go to the auction and have her go with me and Pastor Caldwell, because he’s a mechanic,” said Duggar, who invited his sister, Jana, brother, James, and Kendra’s sister, Lauren, and father along.
“Once we’re finished up with the auction, I’m going to take her to the house where I was actually born. It’s kind of on the way home, and then I’ll pop the question to her and ask her if she’ll start a courtship with me,” he explained. “It’ll show her where I started my life and then maybe we’ll be able to start a new portion of life with her there,” he said.
Although the the girls in the Duggar family have received heart necklaces when they entered into a courtship, Duggar decided to switch it up and have something unique made for Caldwell: “a promise ring. Something just a little bit different. It pretty much says that I thought into it more than just kind of doing what the next guy does,” he shared.
“I don’t think she has any idea that this is going to happen today,” Duggar said, and admitted, “I am pretty nervous, but I’m trying not to show it.”
“I’m nervous to enter into a courtship. That’s always something that every guy should be nervous about,” he continued.
“Kendra thinks that the only reason we’re going to the auction is to look for a car for her mom and also for Jana. And then I’m always looking for a good deal just because I buy and sell cars,” he explained. “But the real reason was actually because we need a good reason to go there to get her on that side of town. I’m going to take her to the house that I grew up in and I’ll ask her to start a courtship with me there.”
After spending some time at the car auction, which Caldwell had visited a handful of times before, the group made a 10-minute drive to the lot of land where the Duggar family used to live. As the two sets of family members walked around the grassy grounds and on the slab of concrete where the house used to stand, Duggar opened up about past memories made there — being born in the home, playing kickball with his siblings and spending time in the living room — before he asked asked Caldwell about courting.
“Anyway, I guess it’s kinda neat seeing my past — kinda seeing where I come from, where I started. And I was wondering if you wanted to go to the next step of courtship with me?” he asked her.
Without hesitation — and with a big grin on her face — Caldwell exclaimed “Yes!” as he put the ring on her right hand.
“I didn’t know you were going to ask me today,” she said to him. “It means we can hug.”
“I had no idea. I thought we were just going to be going to the auction. … I had no idea he was going to ask me to court him,” said Caldwell.
For Duggar, it was “a big relief to me just knowing that now I’ve actually entered a new phase of life.”
Despite his nerves earlier in the day, Caldwell loved Duggar’s thoughtfulness that made the day picture perfect.
“I thought it was really special the way he asked me to court him,” she shared. “Just seeing the place that he was born and had grown up. I’d actually really been wanting to see that place and he told me he was going to show me at some point.”
After entering into a courtship, the couple shared a side hug and sat beside one another in the car ride home as they made a list of courtship standards prior to arriving at the Duggar household, where she showed off her silver ring.
“The ring is silver with both of our names on it, so it’s really special,” Caldwell explained.
“It’s just something to remind her that she knows whenever she looks at it, she can remember that we’re not looking around,” said Duggar. “I’m waiting for her and I know the same thing about her for me.”
“It is an amazing feeling to be husband and wife,” Duggar exclusively told PEOPLE. “It’s something that I’ve always dreamed of to have a wife and to raise a family in a way that honors the lord. We are to very excited to see what God has in the future for us.”
Counting On airs Mondays (9 p.m. ET) on TLC.