Matt Roloff & His Girlfriend Caryn Chandler: A Timeline of Their Relationship

Bethany Quinn | Aug 2, 2018 Celebrities
Matt Roloff & His Girlfriend Caryn Chandler: A Timeline of Their Relationship

Matt Rolfof and Caryn Chandler

Reality TV lovers' hearts were broken when Little People Big World stars Matt and Amy Roloff called it quits in 2016 after close to 30 years of marriage. When we first met the couple back in 2006, they were working on their family pumpkin farm, raising their four children -- twins Zach and Jeremy, Molly, and Jacob Roloff --  and seemingly shared an unbreakable bond. Things, however, started to get rocky in recent years that ultimately led to the couple filing for divorce. LPBW fans got a firsthand look at the Roloff's split and witnessed many awkward moments. Both have since moved on with Amy dating Chris Marek, and Matt finding love with Roloff Farms manager Caryn Chandler.

Since they officially become an item, there have been lots of questions swirling around Matt Roloff and his girlfriend Caryn. When did they officially get together? Did they get engaged? Did they break up? Did Matt cheat on Amy with his now love? Will they stand the test of time?

While we don't have a crystal ball to predict the future -- or a private investigator dedicated to digging up their past (seriously, who as time for that?), one thing is pretty clear: these two are in it for the long haul. Matt and Caryn's romance continues to go to the next level with their love becoming stronger and stronger by the day. They obviously deeply care about each other and seem dedicated at making things work.

Here's a look at the timeline of Matt and Caryn's relationship, the ups, the downs, the rumors, and everything in between.

  • A Relationship Spans a Decade


    Little People, Big World fans likely know that Caryn has been involved with Roloff Farms for quite some time. She reportedly worked her way up to being the farm manager and, as Matt says, is pivotal to making sure things run smoothly. "Caryn is instrumental in running pumpkin season, she's run it for 10 years," Matt Roloff once explained during a LPBW episode. "I enjoy her immensely. Whether we're working or whether we’re relaxing, we have a great time together."

    Obviously, Matt was married to Amy during the time he started working with Caryn who was also married at the time.
  • Office Romance?


    As one might imagine, a number of Roloff fans have wondered if Matt cheated on Amy with Caryn as they had an employer-employee relationship (well, technically, they still kinda do) prior to getting romantically involved. Though he's denied it, Matt's 2007 book, Little People, Big Values, had some people thinking the reality star hinted at an infidelity. "While Amy puts commitments at or near the top of her list, I would put it further down," Matt Roloff confessed in his book. "Amy tends to be more of a committed-to-a-fault kind of person, while I see most commitments -- with some very notable exceptions -- as flexible and negotiable."

    Obviously, that doesn't automatically implicate Matt, but still raises questions (and a few eyebrows).

  • Making It Official (Online)


    It ain't official until it's on social media! Matt Roloff confirmed his relationship with Caryn back in March 2017 after sharing a photo of the duo at Zach and Tori's baby shower -- prompting fans to ask if the two were an item. "Yes, I've started dating Caryn," he replied.

  • Rough Transition


    Matt and Amy's son Zach seemed a bit uncomfortable about his dad's new girlfriend in the past. "Caryn's part of the Roloff farm operation. As far as their relationship goes. I don't have anything to say about it," he once said during an LPBW episode. "My parents are divorced, so yeah."

  • Things Are Still Weird Between Amy & Caryn


    "It is hard for me to say, 'Yeah, go ahead and invite Caryn,' because it is someone I've known for a long time," Amy Roloff once confessed about Caryn Chandler on Little People, Big World. "Matt's worked with her for many, many years, and that will always hurt to some degree, but it's something that I will have to be an adult about it. It doesn't mean I have to embrace it and accept it personally ... "

    Needless to say, things between Caryn and Amy aren't super stellar and should be labeled a work in progress -- and that's putting it nicely.

  • The Kids Are Alright


    While the divorce came as a shock, Matt and Amy's kids have adjusted to their parents' new relationships which is evident by the number of pictures Matt posts of his happy family.

  • 'Gold Digger' Accusations


    For some reason, Roloff fans love throwing out that they think Caryn is a "gold digger" for dating Matt. His poor girlfriend often can't catch a break as dang near any and every photo of her with Matt -- looking in love and happier than ever -- sparks accusations she's with him for financial gain.

  • Matt Is One Protective Boyfriend

    Try not to piss this reality star off as he'll clap back in the name of love. Matt is no stranger to defending his romance with Caryn and reminded Little People, Big World fans he reads his comments, hinting at the need for them to be nice.
  • Snowbirds


    It's not uncommon to see Matt soaking up some sun during the winter months. The reality star and Caryn spend a considerable amount of time in Arizona, the state Matt's girlfriend is proud to call home. It's pretty safe to assume this duo hangs out with Caryn's family (she has two children from a previous marriage) while they're in town.

  • Getting Rid of the Farm in the Name of Love


    Say what?? During the recent season of Little People, Big World, Matt Roloff hinted he might get rid of Roloff Farms if Amy doesn't start accepting Caryn. ".... We were talking about if Amy would sell out the farm, or should I build on the farm," Matt said to Caryn on the show. "But the biggest thing is if I can build here and know that one day maybe I can convince you to move in with me and live on the farm. "But if she's never going to accept, or that's never a possibility then we have to start getting rid of this farm.

    Looks like someone is serious about his relationship.
  • Business Partners


    Matt made it known on Little People, Big World how interested he is in renovating homes and flipping them to sell for a profit. He even discussed Caryn getting in on the action as a possible joint venture the two could enjoy together. Back in June, Matt gave a glimpse of his home renovation in Oregon he quickly sold.

  • Moving in Together


    On the season finale of Little People, Big World back in June, Matt and Caryn were looking for a home down in Arizona they could call their own. But word is the pair purchased a place in Surprise, Arizona back in May 2017 that actually turned out to be Caryn's parents' house.

  • Engagement Rumors


    Back in March, Matt sparked engagement rumors thanks to a cryptic post that had fans wondering if he popped the question to Caryn. "Oh my goodness ... wait until you hear ... better watch new episodes this Tuesday ..." he wrote in his Instagram post.

    (Spoiler alert: They're not engaged ... yet.)

  • Breakup Rumors


    Roloff fans don't miss a beat as peeps noticed Matt Roloff unfollowed Caryn on Instagram around the time speculation started to build they called it quits. It was a minute before LPBW fans saw a photo of the duo together, but Matt silenced all hearsay after sharing a pic of him and Caryn together in Arizona -- putting an end to rumors they were no more.

  • Still Going Strong


    Regardless of the rumors and criticism, Matt Roloff and Caryn Chandler are in it for the long haul. Who knows what's in store for these two!


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