'Little People, Big World' Star Caryn Chandler Has Kids From Her Previous Marriage — Let's Meet Them

Longtime fans of Little People, Big World were heartbroken when Amy and Matt Roloff announced in March 2014 that they were separating (they later filed for divorce in June 2015) after 27 years of marriage. Although it's not clear when, exactly, Matt started dating former Roloff Farms manager Caryn Chandler, fans have speculated that things were romantic between them before he officially split from Amy — making viewers' feelings toward Caryn even more complicated.

As they have gotten to know Matt's girlfriend more through the years, via the TLC series and social media, they've wondered about Caryn's kids. Let's take a closer look at Caryn's previous marriage and her two children.

Caryn was married to Joseph Chandler for roughly 20 years before he filed for divorce in 2012. During their marriage, Caryn and Joseph welcomed two kids: a daughter named Brittany and a son named Connor.

Reportedly, Caryn's ex-husband refused to allow their kids to visit Roloff Farms because according to court documents, per Radar, Caryn wasn't allowed to expose them to TV cameras without Joseph's permission.

During a Season 19 episode of Little People, Big World that aired in May 2019, Brittany and Connor briefly appeared alongside their mom and Matt.

"I wanted to bring my kids to the farm to have lunch with Matt," Caryn explained on the show. "As we continue to get closer and plan a future together, it's really important to me for you to have a relationship with them and I know they would like that as well."

Matt added, "Back when Brittany and Conor were young they used to come and help out during pumpkin season. So her kids know my kids well and I look forward to her family and my family getting closer."

Although Brittany and Connor didn't initially appear on Little People, Big World, photos of Caryn's kids have often popped up on her Instagram account. A September 2018 post featured a shot of her and Brittany alongside a recap of the prior few months.

"What a great summer it has been!" Caryn wrote. "Had both my kiddos home with me. Connor got his first car ... Britt graduated from OSU ... went on vacation with my parents to celebrate her graduation. Had fun traveling with Matt for his 'Little Lucy Big Race' book tour. Lots of memories ... getting excited for beautiful fall in Portland."

Connor has struggled with drug addiction in the past, and he's had a number of run-ins with the law in recent years. In 2016 and 2017 he was arrested for theft, per The U.S. Sun.

Although he revealed in 2018 via Facebook that he was sober, unfortunately, his legal troubles didn't end there.

On Jan. 11, 2020, Connor was arrested and charged on two counts of harassment against Caryn, to which he pleaded not guilty. He “did unlawfully and intentionally harass or annoy” his mother by subjecting her to “offensive physical contact,” according to court papers, per The Sun. As a condition of his release, Connor was ordered to have no contact with Caryn and her family and not to go within 100 feet of her.

In May 2020, he was hit with two additional charges of "attempted use of physical force or the threatened use of a deadly weapon" and "did unlawfully and intentionally damage property, the property of Caryn Chandler," to which he also pleaded not guilty, per the outlet.

In August 2020, a bench warrant was issued for his arrest after he failed to appear at his settlement conference; he was arrested on Aug. 28 and released the same day. When he missed his Nov. 23, 2020, court hearing for a status check, a warrant was issued for Connor's arrest. He turned himself in on Nov. 30.

Though Connor had eventually pleaded guilty to misdemeanor criminal mischief, the other three charges were dropped.

After Connor revealed in April 2021 that he and his girlfriend Ashley were expecting a baby, it appeared Connor was on good terms with his mother, as Caryn helped throw a gender reveal party.

Connor and Ashley welcomed baby boy Liam that August. But the couple unfortunately ended up splitting, with Ashley filing for sole custody in November 2022. Per court documents obtained by The U.S. Sun, Ashley described Connor's alleged “erratic and unsafe” behavior as well as his "anger issues" and "narcissistic gaslighting behaviors.” Though Connor fought for joint custody, he lost his case in February 2024.

During Season 25, Episode 4, which aired in March 2024, Caryn said her daughter Brittany was happy about her engagement to Matt Roloff, but she never said anything about Connor. It's unclear if Caryn and Connor are close at this time.

You can catch new episodes of Little People, Big World Tuesdays at 9 p.m. EST on TLC.