Little People, Big World’s Matt Roloff and Caryn Chandler’s Relationship Timeline

Little People, Big World star Matt Roloff found a second chance at love with Caryn Chandler following his split from Amy Roloff.

The pair’s dynamic began as a friendship before things turned romantic as Caryn worked at the Roloff family’s farm for many years. (Matt and Amy were married from 1987 to 2016 and share four children: twins Jeremy and Zach, daughter Molly and son Jacob.)

After finalizing his divorce, Matt and Caryn revealed in March 2017 that they were dating.

“Caryn’s been the farm manager on Roloff Farms for a number of years, and we have a great working relationship. And we are officially dating,” Matt said in a 2017 episode of the TLC series. “I had to do a lot of soul-searching and think about what I, you know, really wanted in life. Caryn offers me great companionship and I think Caryn and I enjoy the same sort of social settings, you know? We enjoy each other’s company and friendship and companionship. Maybe Amy and I didn’t have that. It’s different. This is, you know, a really neat person, that’s full of life and I think she’s cute.”

Matt and Caryn took their relationship to the next level when he proposed in April 2023.

“After six wonderful years together, I asked Caryn to marry me, and she said ‘Yes!’” Matt said in a statement to People at the time. “Our plan is to enjoy our engagement, and we are looking forward to a simple but elegant wedding in 2024.”

The twosome ultimately did not walk down the aisle in 2024. The following year, Matt announced that he and Caryn had called off their engagement.

Keep scrolling for a complete timeline of Matt and Caryn’s relationship:

March 2017

After going public with their romance on LPBW, Matt and Caryn made their relationship Instagram official.

“Broke away [from] the farm for a day at the Oregon coast. Amazing beauty! Love to you all,” Matt captioned a photo of him and Caryn at the beach.

February 2018

The duo enjoyed time out together as a blended family.

“Caryn and I out for dinner last night with Zach, Tori, Jackson and Caryn’s daughter Brittany,” he wrote alongside a selfie of him and Caryn. “Good times — we all got to take turns playing with Jackson.”

November 2018

Matt and Caryn took a family trip to Maui and got to spend quality time with his grandson.

“When you get the call to spend the day with your grandson over in Maui while Zach and Tori explore the road to Hana — you don’t say no,” Matt wrote via Instagram alongside a snap of the trio. “Anything to spend some time with this little fella and @carynchandler1 .

September 2019

Matt brought Caryn as his plus-one to celebrate Jacob’s wedding to Isabel Rock.

“We all had such a wonderful time at the reception.. So many families merging from all over the globe,” he wrote via Instagram. “Family came from Iowa, Michigan, Florida, Chile, London, India, California, NY, Oregon just to name a few. (&in no particular order lol). All celebrating Jacob and Izzy’s union in the most Special way! @carynchandler1 and I sat back in amazement of the entire event… even the part where it poured rain was fun and exciting! :)).”

August 2021

After four years of dating, Matt and Caryn moved in together and relocated to Arizona.

“Our grand plan right now is to stay committed, stay in love, go to Arizona and spend a tremendous amount of time together,” Caryn said in a confessional. “When we’re here in Portland, we’ll live individually and see each other a lot.”

Matt shared that the move was “a whole new major chapter in life.”

April 2023

Matt and Caryn got engaged.

March 2024

The couple enjoyed some time together while on a cruise.

“Caryn and I back from our cruise… just in time to watch #lpbw My new fav island #curacao very nice!” Matt wrote alongside a snap of him and his fiancée on the boat.

July 2025

Matt announced that he and Caryn split after eight years together.

“Hi everyone, I have some tough news to share. Caryn and I have decided to part ways & end our engagement. Life’s a continued journey and this is the right step for us at this time,” he wrote via an Instagram statement. “[We] will always appreciate the many wonderful memories we have shared. Your support means the World to me and I’m committed to moving forward with positivity and trust in the path ahead. Much love to all.”