Matt Roloff Met Caryn Chandler When She Was Still an Employee at Roloff Farms

Since Amy and Matt Roloff finalized their divorce in 2016, both Little People, Big World stars have started relationships with other people. Amy is happily engaged to Chris Marek, and the couple is planning a 2021 wedding. As for Matt? He's currently dating Caryn Chandler, who lives on the farm with him and frequently appears on the TLC series. Over time, viewers have likely wondered: How did Matt and Caryn meet, anyway?

This was probably a bit awkward at first — especially for Amy, who only recently moved off the family's farm — but Caryn is actually a former employee of Roloff Farms.

Caryn worked full-time for the family business for 10 years, first as a manager and then as Matt's personal assistant. According to Matt, Caryn had been "instrumental in running pumpkin season" until she was no longer employed by the Roloffs as of 2018.

“I enjoy her immensely. Whether we’re working or whether we’re relaxing, we have a great time together,” Matt said on LPBW.

Unsurprisingly, there was speculation that Matt had allegedly cheated on Amy with Caryn. This rumor was never confirmed by Matt or Caryn. However, Amy opened up about her experience in her book, A Little Me.

“Matt was spending more and more time at the tavern he often frequented in the evenings after filming and working on the farm, and our farm manager seemed to be around more and more often as well. What, if anything, was going on?” Amy wrote, per People.

“Then it dawned on me. Matt and our farm manager, who had been working for us a number of years by then, seemed to have more than just a working relationship or friendship. I saw messages, pictures, and other things that should not have been shared between people who just worked together and were still married to other people,” she explained. “I was devastated.”

Amy later added, “In hindsight, I know I should have said something right away, but I didn’t. I was scared and ashamed anything remotely like this could be happening. Was Matt really interested in someone else right in front of me? Why would he even go there when we were still married?” 

No, Matt and Caryn aren't engaged — but they definitely plan to be husband and wife one day. The couple's Instagram followers were faked-out back in February 2020 when Matt shared a photo of himself and his significant other. “Well! it’s official!! The waiting is almost over.. All the new episodes of #lpbw that we’ve been working on the past 6 months will now Air in just over a month March 31st 2020 is the date little people big world will return,” we wrote.

At first, a number of fans incorrectly assumed Matt was making an "official" announcement about his and Caryn's engagement.

“Well that’s coming down stream I hope,” Matt replied at the time. “We don’t want to step on Amy and Chris’s excitement — But you never know what might happen next! For now @carynchandler1 and I are living a very happy and our very best life together… enjoying our kids and my grandkids. A wonderful season of life!”

Their relationship seems to have survived social distancing, as both Matt and Caryn have still regularly posted about each other ever since the novel coronavirus pandemic upended life in the U.S. So who knows? Perhaps Season 21 will feature Matt proposing to Caryn!

Watch Little People, Big World at 9 p.m EST. on Tuesdays on TLC.