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Dean Unglert Says Caelynn Miller-Keyes Cried for an Hour Ahead of His Proposal: She Was ‘Very Angry’

Caelynn Miller-Keyes Cried for an Hour Ahead of Dean Unglert Proposal
Caelynn Miller-Keyes and Dean Unglert Broadimage/Shutterstock

Not quite Paradise. Caelynn Miller-Keyes and Dean Unglert recently got engaged, but the proposal wasn’t exactly a fairy tale.

Related: Dean Unglert and Caelynn Miller-Keyes’ Relationship Timeline

“Caelynn was very angry at me for taking her there. She asked if we could turn around 55 times,” Unglert, 31, explained during the Monday, October 31, episode of his “Help! I Suck at Dating” podcast. “She was crying. She was angry. She was cursing at me, but she stuck with it and she eventually finished it.”

The California native set up his proposal by bringing the former pageant queen, 27, on a grueling 22-mile hike in Hawaii that the duo completed over three days. The first part of the hike went smoothly, but by the second day, Miller-Keyes was not pleased.

“It was a trying experience,” the Bachelorette season 13 alum recalled. “I was thinking too it’s pretty funny to make the person that you’re going to ask to marry you cry on the day that you’re gonna propose to them. … Caelynn cried for, like, an hour that day.”

Related: ‘Bachelor in Paradise’ Couples Who Are Still Together

Unglert went on to admit that the hike actually was “scary,” adding: “She could’ve died. People die on this hike, like, semi-regularly.”

The former Bachelor Winter Games contestant said that he did offer to turn around, but the Virginia native wanted to press on — even though she had no idea there was a proposal coming. “When she was losing it during the difficult part of the hike, in my head, I was like, ‘I’m going to ask you to marry me in, like, four hours, so you need to turn this attitude around,'” Unglert joked.

Caelynn Miller-Keyes Cried for an Hour Ahead of Dean Unglert Proposal 2
Caelynn Miller-Keyes and Dean Unglert Sara Jaye Weiss/Shutterstock

The couple met in 2019 while filming season 6 of Bachelor in Paradise, but their romance wasn’t always a sure thing. Early on, Unglert dumped Miller-Keyes on her birthday, telling her that he didn’t think their lifestyles were “compatible.”

The podcast host left the beach solo, but he returned a few days later and asked the Virginia Commonwealth University graduate to leave Paradise with him. While they’ve been going strong ever since, Unglert wasn’t initially sold on the prospect of marriage.

Related: Everything Dean Unglert and Caelynn Miller-Keyes Have Said About Getting Engaged, Marriage

“She does joke around about us getting married all the time, and I always say, ‘Sorry, it’s not going to happen,’” he told Us Weekly in December 2019. “I don’t know, I’m super unconventional and she obviously is a little more conventional. We joke around about it. Just try to keep expectations to a minimum, you know?”

Unglert obviously changed his mind, revealing during an August episode of his podcast that he’d already decided how he was going to pop the question. “I know when I’m doing it and where I’m doing it,” he explained, adding that he knew Miller-Keyes wanted to propose to him. “My money’s on me doing it first. … We’re gonna elope, I hope. That’s my dream.”

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