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Little People’s Matt Roloff hints at proposing to longtime girlfriend Caryn Chandler as fans go wild

Little People’s Matt Roloff hints at proposing to longtime girlfriend Caryn Chandler as fans go wild

LITTLE People, Big World star Matt Roloff has dropped a major hint he plans to propose to his girlfriend of six years, Caryn Chandler.

Matt, 61, took to Instagram to share his plans to build his dream house when a fan popped a big question.

Social Media – Refer to SourceLittle People, Big World star Matt Roloff may be planning to propose to his girlfriend Caryn Chandler[/caption]

Social Media – Refer to SourceMatt and Caryn have been dating for six years, and a fan wondered when the star is planning to pop the big question[/caption]

On Friday, Matt shared he began the process of building a new home on his $4M Oregon family farm property.

The LPBW star intends to move into the home with his long-time girlfriend Caryn, 55.

However, a fan changed the subject in the comments section.

“Where’s the big diamond ring?” the person boldly asked.

Matt replied: “Well, well. You just have to wait and see what happens.”

Other fans commented on Matt’s response which alluded to tying the knot with Caryn.

“Get that prenup, buddy,” one user harshly said.

Another encouraged: “You’re a creative guy. Can’t wait to see your proposal!”

Yet a third supported: “They make each other happy and that’s all that matters.”


If marriage is in Matt’s future or not, he has big building plans on the horizon.

Recently, Matt shared he broke ground on his new home and credited his youngest son Jacob for helping him with the new building endeavor.

Matt captioned his post: “After 5 years of planning… that first bit of rebar gets put down… it’s going to go up fast from here… hopefully.”

As the family patriarch begins construction on his long-awaited new home, he has praised his son Jacob, 26, for helping in the process.

In a previous Instagram post, the TLC star snapped his son hard at work building the family’s new home.

Wearing a pair of work overalls covered in dirt, Jacob kept his head down as he walked in front of a wood chopper.

“The Mill man at work… helping his Dad cut wood for the new house,” Matt captioned the photo.

Matt, however, did not mention Jacob’s older twin brothers Jeremy and Zach.


Matt and the twins had a falling out after the Roloff patriarch refused their offer to purchase the family farm and decided to sell a portion of the property instead.

The father-of-four, however, recently claimed that his relationship with at least Zach is slowly improving.

“The status of the relationship, if I had to summarize it, I would say it’s on the right path,” the star explained in an interview with ET online.

“I’m talking to Zach every day, it’s not easy but it’s going in the right direction I would say and we don’t have big expectations.”

Confirming that he hasn’t sold the farm, Matt said: “Plan B is actually taking place right now.

“All of the families that looked at the farm but couldn’t get their heads around the long-term commitment of purchasing it are now gonna be able to stay here as a short-term rental.”


Previously, The U.S. Sun exclusively revealed Matt has put measures in place to keep control of the farm even after his death. 

In a Bargain and Sale Deed exclusively obtained by The U.S. Sun, Matt transferred parcels of land from Matthew J. Roloff to Matt Roloff Living Trust for a sale price of $0 on June 24, 2022. 

The parcels of land include 15.68 acres, 16.60 acres, 91.56 acres, and 19.97 acres, making the total 143.81 acres. 

Moving the acres into a trust came just weeks after he put 16 acres of the farm up for sale for a whopping $4million on May 12.

Beverly Hills attorney Adam Michael Sacks exclusively explained to The U.S. Sun why the reality star would transfer the farm to a trust. 

The attorney explained how the trust could come in handy amid Matt’s feud with his twin sons. 

He said: “The trust can make a plan to maintain the property until he dies, or give it to the kids, or give it to whoever. They have to do what the trust says. 

“If your father is not married and passes away, his kids can just split the property. But if he makes a will, he can say, ‘I don’t leave anything to my kids.’ If he doesn’t want his kids to get it and puts it in a trust, the kids can’t fight over it. It’s whatever the trust says. 

“If he didn’t have a will or trust, it would go to the next relatives. If he has a will, he does what the will says. When you set up a trust, you do need to spell it out.”

A trust could also protect Matt legally, as Michael explained: “This can be for legal lawsuit liability reasons. If you’re a doctor and your patient sues for malpractice, if you have a multi-million house in your name, they can take it from you. So you put the house in a trust. 

“The trust is a separate entity, it’s holding it for you. If you lose a lawsuit they can’t go after the trust. It protects you from liability. The trust becomes the owner of the property.”

Instagram/mattroloffMatt posted he broke ground on building his new dream home on the $4M Oregon family property[/caption]

Social Media – Refer to SourceMatt told his fans they’ll ‘have to wait and see what happens’ for when he will propose[/caption]

Instagram/mattroloffHe also credited his youngest son, Jacob, for helping him with the construction process for the new home for Caryn[/caption]

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