So Much Love! See Jill Duggar and Derick Dillard’s Relationship Timeline From Courtship to Parenthood

A love so strong. Jill Dillard (née Duggar) and her husband, Derick Dillard, have made headlines in the wake of their Amazon Prime Video documentary, Shiny Happy People: Duggar Family Secrets, which premiered on June 2, 2023. The doc goes inside the Duggar family’s involvement with the Institute in Basic Life Principles (IBLP) and the abuse that Jill and her 18 siblings endured growing up. The four-part series has reportedly caused a rift between Jill and some Duggar family members, but she and Derick appear to be closer than ever.

Jill and Derick’s relationship timeline is a tricky one — after all, the former Counting On stars both grew up in Arkansas, only 45 minutes away from each other. And even after they met and had chatted a bit on the phone, the wheels were set in motion, but they had not entirely taken off. In fact, Jill’s father Jim Bob Duggar is mostly to thank for this courtship getting off the ground. Keep reading to check out a recap of Jill and Derick’s relationship timeline thus far.

2011: Jill and Derick Cross Paths for the First Time

Jill and Derick first laid eyes on each other during the Christmas season, according to Us Weekly. They met when Derick stopped at the Duggars’ house with a group of people Christmas caroling.

“Neither of us remembers each other specifically from that time; all I have is a vague memory of the group of people who came,” Jill wrote on her wedding website. “Not long after this, Derick contacted my dad and asked if he would be a prayer partner during his two-year term in Nepal.”

Even though that was when they first crossed paths, it would be a while before Jill and Derick started officially courting. Jim Bob was the one to move things along.

2012: Jim Bob Keeps in Contact With Derick

Jim Bob said yes to Derick’s request, and they worked together as prayer partners during Derick’s humanitarian work in Nepal.

“We would talk every couple weeks or so to discuss how our work was going and what current prayer needs were,” Derick explained. But little did he know, Jim Bob had more in store for Derick: he actually tried to play matchmaker. “Jill’s dad would also mention periodically the work Jill was doing in her studies as a student midwife and her desire to someday use her skills overseas on the mission field,” Derick continued.

“As my dad got to know Derick he was really impressed with his Godly character,” Jill added. “He started telling me about Derick and also told Derick about me! I listened in on a few phone conversations with my dad without Derick knowing I was doing so.”

2013: Jill and Derick Begin Courting

March 2013: Finally, Jill and Derick met voice-to-voice over the phone.

“Derick called my dad to give him an update and pray together and I happened to walk in the room,” Jill wrote. “Unlike the other times when I had just listened in, this time my dad told Derick I had just come in the room and asked him to tell me a little bit about himself. We talked briefly that evening, however in the months following I didn’t think much about him.”

August 2013: Up until then, Derick had stayed in contact with Jim Bob but didn’t talk to Jill yet. Instead, he talked to her through divine intervention by “praying about Jill and asking God for direction in getting to know Jill better.” By August, Jim Bob gave Derick his daughter’s phone number just weeks before he left for a two-week trip to Japan.

“[We] began texting, then emailing, then Skyping/talking on the phone… Most of our conversations were centered around our values and life goals,” Jill wrote.

November 2013: Things came to a head in Nepal when Jim Bob and Jill met with Derick overseas for a two-week mission trip.

“I had no idea what to expect,” Derick wrote. “But I was excited and prayed that God would give clear direction during this time. [I] felt the Lord directing me to ask Jill to officially begin a courtship relationship.”

2014: Derick Proposes to Jill, They Get Married

January 2014: Jill and Jim Bob returned from Nepal 60 days before Derick did. And Jill admits she “cried a lot of tears; I missed him so much!” When Derick came home that January, he finally had the opportunity to meet the rest of the Duggar family.

“Upon my arrival home, I was met by the Duggar clan,” Derick wrote. “Over the next few months, I enjoyed spending time getting to know Jill and her family better.”

February 2014: Just one month later, Derick was ready to take the next step. He asked Jim Bob for his daughter Jill’s hand in marriage. Once he got Jill’s father’s blessing and permission, he began planning the proposal. Allegedly, he reached out to a singer/songwriter who crafted Jill a personalized song dedicated to her, just for the proposal.

March 2014: One month after getting permission, Derick went forth with his plans to ask Jill to marry him.

“We went on a lunch date to a Mexican restaurant and then we walked around in a park setting and the guy who wrote the song he was just sitting on a park bench,” Derick revealed. “[The singer/songwriter] was sitting on a bench, nothing out of the ordinary, and was like, ‘Oh, hey, you look like a nice couple. I think I have a song for you guys.'”

As the singer was crooning, Jill recalled how Derick started talking about his feelings. “[He] started saying a bunch of mushy stuff like, ‘I love you so much,’ and I don’t remember everything!”

Then, he offered her a white gold band with a solitaire diamond: a round stone, .63 carats. “I said, ‘Yes, totally!'” Jill wrote.

June 2014: On June 21, 2014, the couple tied the knot in front of 1,000 guests at the Cross Church in Springdale, AK. That’s not all they shared in front of a thousand witnesses — the newly-married duo also shared their first kiss at the altar!

“We’re just really trying to keep our relationship focused not on the physical but really just more on communication and continuing to learn more about each other,” Jill explained. “We’re saving our first kiss and things beyond that for our wedding.”

2015: Jill and Derick’s First Child Is Born

The newlyweds welcomed their first child together, Israel David Dillard, on April 6. He was born a week later than his original due date.

2017: Jill and Derick Welcome Their Second Child

Jill and Derick welcomed their second son, Samuel Scott Dillard, on July 8, 2015. “He weighs 9 pounds, 10 ounces and is 22 inches long. After 40 hours of labor, he was delivered via C-section at the hospital. Thank you for your continued prayers and support!” the couple wrote on Instagram at the time.

2021: Jill and Derick Experience a Miscarriage

In October 2021, Jill and Derick revealed that they had been expecting a third child, whom they were going to name River Bliss. Unfortunately, the couple suffered a miscarriage.

“Even though it was too early to tell the baby’s gender, we picked a name that we feel encompasses our baby’s significance and the life we will always remember,” the couple shared on their blog.

2022: Jill and Derick Introduce Their Third Son

After announcing Jill’s pregnancy in February 2022, Jill and Derick welcomed their third son and rainbow baby, Frederick “Freddy” Michael Dillard, in July. 

“Freddy’ Frederick Michael Dillard is here! He was born 7/7/2022 at 5:16 pm weighing 7lbs. 6oz. and is 20 inches long,” the couple shared in a blog post. “Frederick means ‘Peaceful Ruler’ and Michael means ‘Gift from God.'”  

2023: Jill and Derick Celebrate Their 9th Wedding Anniversary

In June 2023, Jill posted wedding photos on Instagram in honor of her and Derick’s ninth wedding anniversary. In the caption, she called him “the man of my dreams,” “bestie forever,” and “the best man on the planet.” That’s some serious love!