Matt Roloff, the star of the “Little People, Big World” reality TV show, initially sparked interest in how he handled their congenital condition, a common form of dwarfism, while working on his family farm. However, a lot changed during 24 seasons, which aired between March 2006 and January 2023, including his divorce in May 2016 and his ex-wife’s marriage to Chris Marek. Matt was lagging as the only unmarried family member at the end of the 24th season; however, that potentially changed in April 2023, when Matt announced that he was engaged.

Matt has been dating Caryn for six years

After working together on Roloff Farms for many years, Caryn Chandler and Matt started a romantic relationship in 2017. Following over half a decade of dating, he announced on social media that he’d proposed to her, and that they plan to have ‘a simple but elegant wedding in 2024.’ That was expected; they had a lot of time to get close and work out all the kinks in their relationship, particularly handling their living situation and the children from previous marriages. Additionally, both are close to each other’s parents.

They met at his farm

Caryn was his long-time employee, and had been working as a farm manager and assistant as early as 2008. However, after the two announced in season 17 that they’d begun dating, she slowly reduced her obligations before quitting the position in 2018. Matt noted that she was instrumental in organizing each pumpkin season, and that she still helped ensure things were running smoothly, despite being unemployed on paper.

He refused to speak in detail about their relationship, when it started, as there have been rumors that he cheated on Amy. Matt only told the producers, ‘Caryn and I have developed a great friendship over the years. Her sense of logic and my sense of logic are very compatible.’ He also responded to the rumors by clarifying that he has no regrets over his 26-year-long marriage, but that the two had outgrown each other in some areas and that his heart was open for Caryn.

His family wasn’t happy; Amy said in June 2022 during an interview with Us Weekly that she would prefer not to attend their wedding; her husband, Chris, said that they wouldn’t even get a chance. According to him, Matt and Caryn had told them it would be small, perhaps only the two in front of witnesses. With that in mind, they both knew how the wedding day would look, but were waiting for the right time. Matt’s last direct response was in 2021, when the producer asked him if he plans to get married, and he replied that it wouldn’t happen until at least 2022.

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Caryn reportedly wanted to quit the show

Although their relationship seemed stable, an insider almost ruined it all with rumors that Caryn decided to quit in November 2022, shortly before season 24 wrapped up. According to them, Caryn was ‘completely done, and had too many disagreements with Matt on what to say and do on air, and has become tired of family drama.’

Caryn and Matt had a strained relationship following the drama around selling Roloff Farms; as a reminder, Matt refused to let his sons Jeremy and Zach inherit the property, and turned down their purchase offers for being too low. He put it on the market for $4 million but ultimately turned it into an Airbnb-style property, in partnership with the iTrip Vacations company.

She allegedly gave Matt an ultimatum

Another indicator that Caryn was distancing herself from the show was her time in Arizona. After vacationing there in November 2022, an insider alleged that she wanted to move permanently there, likely by January 2023, and that she would give Matt an ultimatum, deciding the future of their relationship. That was partially true; the couple purchased Caryn’s parents’ home for about $550,000 in 2018, before she rented out her $405,000 home in Oregon. Additionally, her parents only lived a mile and a half away.

Matt explained that they would spend half the time there since he was tired of staying in hotels, and the home was ‘his refuge, his relaxation, good for the longevity of his heartbeat and conducive to his short stature.’ Caryn explained their plan in the show in August 2018, by saying, ‘Our grand plan right now is to stay committed, stay in love, go to Arizona, and spend a tremendous amount of time together.’ She added that they spend time individually in Portland while still seeing each other.

He confirmed the news to PEOPLE magazine

Although engagement rumors circulated for a while, Matt finally responded on 19 April 2023, telling PEOPLE magazine, ‘After six wonderful years together, I asked Caryn to marry me, and she said yes!’ He then mentioned how they wanted an elegant but straightforward wedding, before going quiet. The next day, TLC posted a picture of Caryn holding his right hand and showing off the diamond engagement ring on the fourth finger of her left hand. The company also included a link in their Instagram profile bio, leading to the page that explains the engagement.

Matt posted a picture of the home a few days before the announcement. He commented that being 61 was equally exhausting and exhilarating, but that constructing his dream home made him happy. He also expected negative comments, and wrote, ‘Building things has always been a passion of mine. Now I’m having fun. Oh… and the negative Nellys out there, sorry you’re not having fun in life.’ That reminded the show’s viewers that he once said that proposing or marrying Caryn ‘made no sense until they had a place to land on.’

Not everyone enjoyed hearing the news

His social media followers had divided opinions on his engagement. The most liked comments disregarded his happiness because he ‘broke’ his previous marriage, alleging that he cheated on Amy. Others suggested that Caryn was with him for his wealth and to get a free house, and that they hoped he had a prenuptial agreement, because they didn’t believe that she loved him. However, many fans defended him, telling him that he and Caryn looked ecstatic about the new chapter in their lives, and were hoping to see them in season 25 of “Little People, Big World.”

Although Amy was disappointed after the divorce, and upset that he didn’t want to sell a portion of Roloff Farms to his sons, the two were later on cordial terms, hence the news didn’t hurt her. As a reminder, Amy got US$975,000 for her share of the family farm, measuring 32.28 acres, after Matt loaned $825,000 in August 2020 to pay it. Thus, while hurtful to his ex-wife and children, his way of sorting out the real estate was legal.

Cheer this photo on!!! That’s the tall and the short of it ! Period. Negative people please go away gracefully…..

Posted by Matt Roloff on Saturday, June 25, 2022

As proof of amicable relations, Matt and Amy got together with their partners during the first weekend of the pumpkin season in October 2022, and invited their son Jacob and his wife Isabel Sofia Rock Their daughter, Molly, hasn’t commented on the engagement, but she lives far away in Spokane, Washington, with her husband Joel Silvius, so she’s largely unaffected. Zach also moved to Washington, and didn’t want his father and his father’s fiancé babysitting their children. He even said that he wouldn’t introduce his son Josiah Luke, born on 30 April 2022, to Matt and Caryn. Jeremy lives the closest to Matt, only a 15-minute car drive away, in Bend, Oregon, with his wife Audrey and three children, sons Radley and Bode and daughter Ember. Like his siblings, Jeremy didn’t comment on his father’s engagement.

Matt’s marriage should work out

His relationship with Caryn was under fire before it even began, yet they were building their dream house and, as promised, he proposed to her while the construction was ending. Furthermore, their wedding should also happen on schedule in 2024, presumably in front of TLC’s cameras for the next season. There have been some hints about their engagement on Season 24 when Matt and Caryn said through laughter that they ‘talk about the next step in the relationship all the time but that they are waiting for all the stars to align just right to marry.’ Over the years, they also mentioned creating one-year, two-year, and five-year plans, and it appears that the marriage portion is coming true as envisioned.

They are overcoming their doubters

Although she wasn‘t skeptical about the success of his relationship, Amy alleged that he exchanged inappropriate messages with Caryn before they’d divorced, and had ‘more than a friendship or a working relationship with her for some years.’ However, she has moved on with Chris Marek, sold her land, and seems happy. Additionally, Caryn explained that time healed their differences by saying, ‘Everything is moving in a good trajectory. We all love our grandchildren. We’re together sometimes, and we make it pleasant.’ Matt also seemingly had no problems pursuing personal happiness, even if it meant burning bridges with two sons.

Moreover, Caryn publicly answered people’s most common doubt, her being a gold-digger, and clarified, ‘I love the farm, but if it went away tomorrow, I would still love Matt, and we would live our life. I know that I’m not with him for this farm.’ She also added that she couldn’t comprehend why people doubted her, because Matt is amazing, and she adores him.

However, the couple has yet to mention how they would handle the situation with Caryn’s two children, son Connor and daughter Brittany. She had them during a 20-year-long marriage with her ex-husband Joseph, but he was bitter after the divorce. For example, he was unrelenting about letting Brittany and Connor appear in the show during a custody battle. However, once they turned 18, they could do so lawfully, and thus were seen during a brief lunch shot in a May 2019 episode. With the new developments in their mother’s romantic situation, they may appear more in the anticipated new season.

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