How Did Matt Roloff From ‘Little People, Big World’ Meet His Girlfriend, Caryn Chandler?

We’ve been keeping up with the Roloff family for years, and there’s no doubt a lot has changed since the beginning. It all began with Matt and Amy Roloff, a couple with dwarfism who showed viewers through Little People, Big World what life is like raising their four children and owning a farm with their condition. Now, family dynamics have totally changed, as Matt and Amy divorced following over two decades of marriage — and they were both have significant others, too.

We’ve seen Matt discuss his relationship with Caryn Chandler on the show, and we’ve also seen them looking totally in love on social media. Here’s how they first met.

Caryn met Matt while working at Roloff Farms

Fans were deeply saddened when Matt and Amy made the choice to separate, but they were also incredibly interested in who Matt would date next. CafeMom reminds us Caryn has been part of the Roloff Farm operations for years, as she was working her way up the ranks to farm manager. As Matt said during an episode of Little People, Big World, “Caryn is instrumental in running pumpkin season, she’s run it for 10 years.” He also mentioned that he enjoyed her “immensely” and that they always had a “great time together” whether they were just working or getting to know each other even more.

When Matt and Caryn first met, both of them were married, so it’s safe to assume nothing happened between them until their divorces. Some fans seem to think otherwise, however. In Matt’s book released all the way back in 2007, Little People, Big Values, he discussed how his value system is much different than Amy’s — and he also stated that he doesn’t value commitment as much as Amy does. Could this mean Matt cheated in the past? Some fans seem to think so.

Amy has also known Caryn for many years

Matt and Amy Roloff
Amy Roloff and Matt Roloff appear on NBC News’ Today show | Peter Kramer/NBC/NBCU Photo Bank via Getty Images

While Matt and Amy made their relationship official on social media in 2017, we’ve established that they knew each other for many years — and, of course, this means Amy also knew Caryn for the same amount of time. Amy has expressed her discomfort in the past regarding the situation, however. Good Housekeeping notes she mentioned on the show that it’s tough to be around Caryn and invite her to events because of their past history. “Caryn is an employee, and is in a personal relationship with my ex-husband, and so it is still hard to invite Caryn to some of the family events. I’d rather just minimize the personal interaction. It’s not healthy for me,” Amy said.

Some fans also suspected Amy might be feeling jealous of Caryn, as she might not want Caryn to have a close relationship with her kids. In Touch Weekly reports one fan tweeted, “It’s obvious Amy is super jealous of Matt’s new girlfriend. Looks like her kids feel comfortable and like her very much too.” And others think Amy needs to move past this discomfort, as Caryn seems to be in it for the long haul and Amy has a new boyfriend anyway.

Some fans suspect Matt and Caryn could be getting engaged soon

There hasn’t been any official engagement announcement yet, but fans seem to think that’s exactly where Matt and Caryn are headed in the near future. Back in March 2018, fans first thought the two were getting hitched when Matt posted this cryptic Instagram photo with the caption, “Oh my goodness… wait until you hear… better watch new episodes this Tuesday..” We know now that the engagement wasn’t the news, but The Hollywood Gossip reminds us at the end of 2018, the rumors of engagement circled around again (though they were squashed by Caryn saying, “not yet.”)

Fans are ready for another Roloff wedding soon. Whether it’s Matt and Caryn or Amy and Chris, it seems like both relationships are headed toward the wedding bells in the near future — we’ll just have to wait and see what happens.

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