An awkward reunion? Little People, Big World stars Matt Roloff and Caryn Chandler reunited with Amy Roloff and Chris Marek for the first time since announcing their engagement.

In a teaser for the Tuesday, March 19, episode, shared by TLC, Matt, 61, and Caryn, 56, visited Amy, 61, and Chris, 61, for a dinner date and Matt hoped the outing would not be “awkward” with his ex-wife.

“I don’t know if she’s going to make this awkward or she’s OK with it,” the father of four — who was married to Amy from 1987 to 2016 — explained to producers. “But we’re going to find out in a few minutes.”

Before their arrival, Chris warned Amy that Caryn’s ring was “bigger” than hers. “The diamond is going to be bigger. OK. How much bigger?” Amy questioned in a solo confessional. “You make it sound like it’s a rock that covers her whole hand but I don’t give into all that stuff.” Almost immediately upon sitting at the dinner table, Amy asked Caryn to “see the ring.”

Matt and Caryn have always been vague about their plans to make it down the aisle but the TLC personality shocked fans by announcing his engagement to Caryn in April 2023. “After six wonderful years together, I asked Caryn to marry me, and she said, ‘Yes’!” Matt told People. “Our plan is to enjoy our engagement, and we are looking forward to a simple but elegant wedding in 2024.”

The pair opened up about their backyard engagement during the March 12 episode of the series, with Caryn telling cameras she had “no idea” that Matt was planning to propose to her.

“The sun has set, so the ambiance was just really cozy and nice,” Caryn explained before Matt decided to get the ring he had hidden in his room and “just go for it.”

“And I pulled the box out at the exact time that I said, ‘Will you marry me?’ And she looked at the box, looked at me, and then she had that feeling like, ‘What’s this?’” he recalled of his proposal. “But she opened the box … there’s good things in this box.”

Matt introduced his relationship with Caryn in 2017, one year after he finalized his divorce from Amy. While Amy married Chris in 2021, Matt’s relationship with Caryn was more controversial, considering she was the longtime manager of Roloff Farms.

“Everybody, I believe, have different people that they jive with at different stages of your life. I have absolutely no regrets looking back over Amy and I’s 26 years of marriage,” the Against All Odds author told producers at the start of his relationship with the mom of two. “We outgrew each other in some way, and now, my heart’s open for Caryn.”

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