Matt Roloff and Caryn Chandler Relationship Timeline Before Their Shocking Split

Matt Roloff, star of Little People, Big World, embarked on a new chapter of his life with Caryn Chandler after his split from Amy Roloff. Their story began as a friendship, blossoming into romance after Caryn worked at Roloff Farms for several years.

Matt and Amy were married from 1987 to 2016 and share four children: twins Jeremy and Zach, daughter Molly, and son Jacob.

In March 2017, following the finalization of his divorce, Matt and Caryn confirmed their relationship.

"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 stated 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."

The couple took a significant step forward in their relationship when Matt proposed in April 2023.

"After six wonderful years together, I asked Caryn to marry me, and she said 'Yes!'" Matt shared in a statement to People. "Our plan is to enjoy our engagement, and we are looking forward to a simple but elegant wedding in 2024."

However, plans for their wedding in 2024 would not come to fruition. The following year, Matt announced that he and Caryn had ended their engagement.

Here's a complete timeline of their relationship.

After publicly sharing 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 them at the beach.

The couple enjoyed a dinner outing with family.

"Caryn and I out for dinner last night with Zach, Tori, Jackson, and Caryn's daughter Brittany," he shared with a selfie. "Good times — we all got to take turns playing with Jackson."

Matt and Caryn took a family trip to Maui, where he made memories 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," he wrote alongside a snap of the trio. "Anything to spend some time with this little fella and @carynchandler1."

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 noted on Instagram. "Caryn and I sat back in amazement of the entire event… even the part where it poured rain was fun and exciting! :))."

After four years of dating, Matt and Caryn moved in together, relocating 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 described the move as "a whole new major chapter in life."

The couple became engaged.

Matt announced the end of their relationship 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 in 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."