Fascinating Facts About Matt Roloff's Girlfriend, Caryn Chandler

Photo: Caryn Chandler / Shutterstock
Matt Roloff's Girlfriend: Who Is Caryn Chandler?
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TLC's hit show Little People Big World has always delivered a lot of emotional moments in its impressive 21-season span. The show is centered around the six members of the Roloff family and their lives near Portland, Oregon. Matt Roloff, Amy Roloff, and their kids have become fan favorites and the show has been through some ups and downs, but persevered and remained one of TLC's most popular shows. Fans were appropriately stunned when the shows patriarch and matriarch, Matt and Amy Roloff announced they were getting divorced. There was a lot of speculation as to the "why?" behind the divorce, including rumors that Matt Roloff cheated on Amy Roloff with Caryn Chandler, who was an assistant on the Roloff family farm at the time. 

Who is Caryn Chandler, Matt Roloff's girlfriend?

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She's worked on the Roloff's family farm for over a decade. Yup, you heard that right. Chandler has worked for the Roloff's pumpkin farm for over ten years, side by side with Matt, Amy, and the kids for quite some time. First, she was a manager, and then she became Matt's personal assistant. 

When questioned about the working relationship on an episode of LPBW, Matt stated, “Caryn is instrumental in running pumpkin season, she’s run it for 10 years. She tries to get Amy as involved as she can. There was awkwardness a little bit, but we’re all kind of finding our way."

She's also the person behind an iPhone video on Matt's Instagram videos.

When is Caryn Chandler's birthday?

Caryn Chandler's birthday is on Oct. 1, which makes her a Libra

Who was Caryn Chandler married to?

During their divorce proceedings, Chandler and her ex, Joseph Chandler, often fought about her job at the farm and he even forbid her from ever bringing their fourteen-year-old son to the farm. 

Oregon court documents show he is also adamant his kids never appear on Little People Big World.

Who is Caryn Chandler's son?

Caryn Chandler's son is Connor Chandler. In January of 2020, he was arrested for harassment in Oregon; however, that wasn't the first time he's been in trouble with the law. In 2016, he was arrested for theft, and in 2016, he was arrested for criminal mischief. He was reportedly serving a five-year probation sentence at the time of his arrest. Yikes.

Caryn also has a daughter, Brittany, who seems to be close with Zach Roloff's wife, Tori. After Tori had revealed that their daughter, Lilah, had dwarfism, Brittany commented on her Instagram photo to show her support and admiration for her. 

"Oh Tori. I’ll be lucky to be half the mama that u are one day," she wrote. "Real and honest. I love u guys & those kiddos so dang much,” Brittany commented. “Britt will always make sure they know how much better this world is because of them!!”

Caryn got a tattoo in honor of Roloff.

In 2017, Chandler was spotted with a tattoo on her ankle with the letter "R" over the word "really". Hmm... is the "R" for Roloff? The timing was a bit suspicious, and she had been sporting the tattoo proudly.

Nothing was confirmed by Chandler, but fans were not too receptive of her or her ink, with some even calling the tattoo "tacky". 

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Roloff's kids are all over Caryn Chandler's Instagram.

 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 

A post shared by Matt Roloff (@mattroloff) on Oct 4, 2019 at 11:10pm PDT

There hasn't been too much drama with Chandler and the kids, especially because she's known them for so long because of her role on the farm. The kids have all stated they want both of their parents to be happy no matter what.

However, Zack Roloff admitted the relationship with his dad's new girlfriend is a bit awkward, especially since she was formerly an employee. Understandable!

You can also see a ton of Caryn Chandler's pictures on Matt Roloff's Instagram.

He regularly posts his gal pal on his profile, and a lot of the time, they're hanging out with his grandchildren. Cute!

 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 

A post shared by Matt Roloff (@mattroloff) on May 22, 2020 at 11:42pm PDT

She appeared on Little People Big World way before becoming Roloff's girlfriend.

Plot twist! Before Roloff and Chandler started dating, she was featured on the show as an employee of the farm — not a big role, but still large enough to have fans recognize her. Can you sense any tension in any of the old episodes? 

What is Caryn Chandler's net worth?

It's no secret fans of the show do not feel all warm and fuzzy toward Roloff's new lady friend. Seeing her start off as a manager, then assistant, and now a part of the family's inner circle has rubbed some devotees of the show the wrong way.

She's been accused on Instagram of being a "gold digger," who's only interested in Roloff for his money. Roloff, likewise, has been accused of "robbing the cradle," even though Chandler is only seven years younger than him.

Her net worth is currently unknown.

She's actively involved with family activities. 

As you can see on the show, Chandler has been invited to a few Roloff family functions, including Audrey's gender reveal party and baby shower. Roloff's kids seem to welcome her, but the encounters between Chandler and Amy (Roloff's ex) are definitely still awkward — you can almost see the tension on the TV screen! 

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Amy claims she's still uncomfortable with Chandler being around (because Roloff cheated?), especially because she's a former employee of theirs. She also expressed her concern that Chandler is having an easier time fitting in with the family than her current boyfriend because of the longtime history she has with the family.

In 2017, Chandler also organized a birthday party for Roloff, and some sources say Amy felt "snubbed out" from the festivities while there. Ouch. 

Are Matt Roloff and Caryn Chandler engaged?

In 2018, Roloff made a cryptic comment that left some fans wondering about a possible engagement announcement. Nothing was confirmed, but wedding speculation remained rampant. 

Roloff has confirmed that the couple aren't getting married yet, but still sees a future with Chandler.

 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 

A post shared by Matt Roloff (@mattroloff) on Mar 15, 2020 at 10:14am PDT

In a podcast interview, he opened up about the status of his relationship, saying, “There’s no immediate wedding bells yet. Caryn and I are kind of waiting to let [ex-wife Amy Roloff’s wedding] excitement play out, but no wedding bells planned [just] yet. I hope one day that there are, and [there] probably will be. Caryn and I are very close. We enjoy each other’s company and friendship immensely... We’re dating and having fun together and living our best lives.”

He also opened up about Chandler's relationship with his children, adding, “My kids seem to really accept Caryn very, very well. They spend a lot of time together. She’s a great, sort of, surrogate [grandma]. They call her Cha-Cha. The grandkids love spending time with her, and she loves spending time [with them]. She’s very, very active in not just accepting the grandkids, but really setting things up and getting me involved. Matt, you’re putting your computer and phone away tonight. You’re gonna be playing games and reading to the grandkids tonight. That’s what you’re doing.”

This seems to be very true, as Tori Roloff recently celebrated Chandler's birthday by praising her on her Instagram Stories. She said in the story, “Happy Birthday. We seriously and honestly could not do life without you.” The message was accompanied by Chandler holding Tori's two young children.

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Molly Given is a writer living in Philadelphia and lover of all things to do with mystery and magic in life. When she’s not writing about entertainment and lifestyle topics, she can be found planning her next adventure.

Editor's Note: This article was originally posted on April 13, 2018 and was updated with the latest information.