Entertainment TV Joseph Duggar and Kendra Caldwell Share a Wheel-y Great First Date – Under Jackson's and James' Watchful Eyes In an upcoming episode of Counting On, Joseph Duggar and Kendra Caldwell go on their first date: rollerblading By Lindsay Kimble Lindsay Kimble Lindsay Kimble is a Senior Digital News Editor and the Sports Editor for PEOPLE Digital. She's worked at PEOPLE for over seven years as a writer, reporter and editor across our Entertainment, Lifestyle and News teams, covering everything from the Super Bowl to the Met Gala. She's been nominated for the ASME NEXT Awards for Journalists Under 30, and previously wrote for Us Weekly while on staff at Wenner Media. People Editorial Guidelines Published on September 18, 2017 01:30 PM Share Tweet Pin Email Kendra Caldwell is skating off with Joseph Duggar‘s heart. In Monday night’s episode of Counting On, Caldwell and Joseph – who said “I do” earlier this month – go on their very first date. Under the watchful eyes of his younger brothers, James and Jackson Duggar, the 22-year-old takes Caldwell rollerblading. “I think I rollerbladed once, but I was really not very good at it, but we’ll see how I do today,” admits Caldwell, 19, going into the date. Opening up about the set-up of their courtship, Caldwell explains, “My modesty standards are very similar to the Duggars’ standards. Wearing skirts down to below our knee, wearing sleeves on our shirts and then pretty high necklines.” The special outing is not brother James’ first rodeo in chaperoning. “I used to chaperone Jill and Derrick, back when they were needing a chaperone,” the 16-year-old explains. “Now I’m starting to chaperone Joe and Kendra. I’ve been doing it for a little while, not too long. I guess you could say I’m a pro chaperone.” Jackson, 13, is a “chaperone in training” – and he seems to be in touch with the basic rules. FROM COINAGE: Your Go-To Guide to Finding the Right Wedding Gift In September – three months of after getting engaged – Caldwell and Joseph tied the knot at the First Baptist Church in Siloam Springs, Arkansas. “It is an amazing feeling to be husband and wife,” he exclusively told PEOPLE at the time. “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.