'Little People, Big World': Matt Roloff's Girlfriend, Caryn Chandler, Brings Her Troubled Son on Screen

While Little People, Big World fans may remember when Matt and Amy Roloff started the show as a married couple, a lot has changed since their series began 14 years ago. Today, Matt and Amy are divorced, though they still live together on the Roloff Farms property. And tensions continue to rise as they decide what to do with the farm.

Matt and Amy may bicker, but overall, they’re still quite amicable, and they both are growing closer and closer with their significant others. Even more recently, Matt’s girlfriend, Caryn Chandler, brought her kids on to the show, too — and after some sleuthing, many learned that her son had gotten into trouble with the law in the past.

Caryn Chandler and Matt Roloff’s relationship seems to be getting more serious

While Amy Roloff met her boyfriend through a single’s mixer party, Matt actually knew Caryn for many years before they became romantically linked. Caryn was employed by Roloff Farms and helped run pumpkin season, the farm’s busiest time. Unfortunately for Amy, the fact that Caryn worked within her family’s business remains a sour point, and it likely also means the two will never truly get along.

The more we watch Caryn and Matt interact and discuss their futures, the more fans are starting to think wedding bells are in their future, too. Engagement rumors started way back at the end of 2018, The Hollywood Gossip notes. And while some took to her Instagram to ask if she had a ring on her finger, Caryn replied, “Not yet.” The “yet” was all fans needed to continue speculating about what the couple’s future would look like. We’re betting if Matt permanently moves off of the farm property, he’ll propose.

Caryn brought her kids on the show now that they’re adults

We’ve seen all of the Roloff kids at one point or another on the show, but Caryn’s kids have been totally MIA. According to Radar Online, Caryn’s son and daughter were not allowed to be on Little People, Big World due to a custody agreement she had with her ex-husband, Joseph Chandler. Now, her daughter, Brittany, is 22, and her son, Connor, is 19. Since they’re adults, they can make their own decisions regarding if they want to be on the show or not — and they finally made their debut.

On the show, Brittany and Connor seemed totally comfortable with Matt, and they asked him about what he’s been up to with the farm and how pumpkin season preparations have been going. It was also confirmed that Caryn is no longer employed with Roloff Farms since she’s dating Matt. And Brittany and Connor commented on how Caryn seems slightly bored since she no longer has work duties, so it’s nice for her to have Matt around.

Her son has been in trouble with the law in the past

It was certainly nice to see Matt spending quality time with Caryn’s kids, but we may not have gotten the full story on screen. Radar Online notes Connor has been arrested twice “for theft and criminal mischief.” The publication adds that Connor was first arrested for “theft in the first degree” in 2016, and the following year, he was jailed again for “criminal mischief in the second degree.” He’s currently serving five years of probation time.

Not only that, but the teen also admitted awhile back on Facebook that he was dealing with drug addiction. “I was 13 years old when i was first introduced to a drug called Xanax. Biggest mistake of my life was choosing to try it [sic],” he wrote. “Almost killed me, almost killed my relationship with my family, almost destroyed my entire life.” Thankfully, he also announced that he kicked his Xanax addiction after undergoing many rehab treatments. He publically apologized to his mom and seems to be doing a lot better ever since. “But just know, its over, and that thats never going to change, i will continue to do good and stay sober for the rest of my life [sic],” he wrote.

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