"We're engaged," Dean said on the October 31 episode of his "Help! I Suck at Dating" podcast.
"It doesn't feel any different though, to be honest with you, because I've already worn the wedding ring for three years and we've already owned a house together for two years. But don't get me wrong, it is beautiful and I am very happy to be engaged."
But Dean can't say Caelynn was "happy" in the moments leading up to his marriage proposal.
Dean said he had planned a grueling 22-mile hike to Hawaii's Kauai Island, where he finally got down on one knee and popped the question.
"It's 11 miles in and 11 miles out," Dean told his podcast co-host Jared Haibon.
"There's a halfway point you can hike to, so it's six miles in and then you camp, and then you finish the next five miles the next day."
Dean joked, "I figured I've tested her so much, there had to have been one final test for her. And she passed! She passed the test, barely though. There were times [she almost quit]."
Dean said he and Caelynn will have vastly different recollections of the hike because he thought it was a "beautiful" experience with "perfect" weather.
Caelynn, however, apparently broke down when, on the second day of their hike to the beach, they came across "a mile-long trek of sheer cliff on one side."
"I thought it was fine. I didn't have an issue with it... Caelynn, on the other hand, was very angry at me for taking her there," Dean recalled.
"She asked if we could turn around 55 times. And eventually I just started saying, 'Yeah, let's turn around. If you want to turn around, let's turn around.' But she didn't, I mean, credit to her because she was crying, she was angry, she was cursing at me."
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But Dean was apparently proud because Caelynn "stuck with it" and "eventually finished it."
"So, yeah, it was a trying experience," Dean admitted.
"I was thinking too, it's pretty funny to make the person that you're gonna ask to marry you cry on the day that you're gonna propose to them. Caelynn cried for like an hour that day."
Jared pointed out how a woman shouldn't cry from fear, pain, or sadness before getting engaged.
"It's supposed to be happy tears that day!" Jared noted.
"Right, and I did everything [I could] too," Dean insisted.
"I moved all of her stuff into my backpack... and I walked ahead a mile, put my backpack down, came back with no backpack, and spotted her as she moved along the cliffs... I was working overtime and trying to encourage her the best I can. But it was scary; there were scary points."
Dean confessed that Caelynn "could have died" on that hike because "people die on this hike semi-regularly."
"It was a reverse psychology thing, like, if I tell her we can turn around, there's no way she's going to want to turn around," Dean shared.
"And there were three moments where I was like, 'Damn, she's really pushing herself here to the full brink of what she can do.' I swear to god, [I thought], 'She's going to have to turn around.' And I would've had no choice... and would've had to figure something else out."
Dean said Caelynn had no idea he was going to propose, and so she didn't have much motivation to get to the end point. She apparently just thought it was "a random hike."
"I can't even put into words how angry she was at me that day," Dean admitted.
Dean ended up popping the question with a temporary engagement ring with a "small" diamond because he claimed to have lost the original 4.5 carat diamond he'd purchased for his girlfriend.
Dean said he hopes to find the original diamond somewhere in his home and then turn the small diamond from his marriage proposal into a necklace for Caelynn.
"I never thought this day would come. I never thought I would propose to Miss North Carolina on a beach in Hawaii, but here we are!... I am stoked and Caelynn is stoked," Dean said.
Dean told Jared that hopefully Caelynn will come on their podcast one day to tell her side of the hike story.
Dean first revealed he was going to propose marriage to Caelynn soon during the October 23 episode of "Help! I Suck at Dating."
When Caelynn confirmed her engagement late last week, she gushed on Instagram, "The hardest and scariest hike I've ever done led to the best day of my life. I can't wait to be velcroed to you forever @deanie_babies."
And Dean posted a video around the same time from the couple's hike and ultimate marriage proposal.
"On the most beautiful beach in the world I got to ask the most beautiful girl in the world if she'd let me be her husband (she said yes)," Dean wrote on his own Instagram account.
"It's been 16 years since I lost my mom. I always thought it'd get easier as time wore on but it hasn't. Something about being an adult just makes me wish she was here even more. Every year around this time I get emotional and depressed, I miss her more now than I ever have before."
Dean continued in his post, "I'm so happy to now have this date as a happy memory as well. From now on I'll be able to find joy in something this time of year, be excited for the future rather than sad about the past, and celebrate love with the woman who may one day be a mother to children of our own."
Dean revealed in June 2022 of potentially proposing marriage to Caelynn on his podcast, "I made a deal with [Caelynn]. I was like, 'I'll buy you a ring if you buy me a truck.'"
Dean admitted at the time how he even threw a "hissy fit" upon seeing the 4.5 karat ring Caelynn was hoping to have on her finger one day and the pair got into "a scuffle."
Dean said getting engaged was simply "a touchy subject" in his relationship, adding, "Caelynn makes significantly more money than I do and here I am having to spend all this money on something I don't even want. Like, I want her to get what she wants, but she's the one who wants to get married."
But then Caelynn came through and bought Dean a truck in August.
"I spent the afternoon at Toyota picking up something special for Dean," Caelynn wrote on an image of a Toyota steering wheel. "If you listen to 'Help! I Suck at Dating,' you know what this is."
That same month, Dean told Jared on his podcast how he knew where he was going to propose marriage and how he was going to do it.
Dean explained how he and Caelynn both plan on proposing marriage to each other, but he noted, "My money's on me doing it first."
And when imagining what his wedding is going to be like, Dean teased, "We're gonna elope, I hope. That's my dream."
Back in April, Caelynn recalled her reaction to Dean's request that she propose marriage to him.
"When Dean first said that, I thought, 'Okay, [it's] another thing Dean is saying to break the mold.' Sometimes he says things just for a reaction, and he'll admit that. I thought that's kind of what he was doing," Caelynn explained in a Q&A on YouTube.
"But the more I thought about it, the more I loved it, because traditionally, he would propose to me. That's something I've dreamt of for so long, and that's something that he doesn't get -- a day that's catered to him and this special moment where he's really thought of. That's when I was like, 'Oh my gosh, I love this.'"
Caelynn pointed out how she and Dean have "a partnership" and so they both deserve to have a proposal day.
"I love the idea of planning this extravagant -- well, not extravagant, because he doesn't like to be the center of attention -- but just this thing that's all about him. So after I really thought about it, I am really, really into it," Caelynn noted.
Dean, who initially rejected the idea of marriage entirely, and his girlfriend of three years have been wearing wedding bands since 2020 to show they are committed to each other.
"I don't need [the] title of husband to show the world that I'm committed to one person, and so the fact that I'm wearing the ring is showing just that... I'm committed to Caelynn and only Caelynn," Dean said on The Bachelor: The Greatest Season -- Ever! special that aired in June 2020.
Dean and Caelynn now laugh about how people never thought their relationship was going to last.
"We definitely defied the odds," Caelynn gushed to Us Weekly ahead of the couple's two-year anniversary in June 2021, adding, "I think we just never really listened to those negative people, and we just lived our lives."
Caelynn admitted, however, it "really frustrates" her when fans assume Dean isn't a good boyfriend.
"He is hilarious and he's very sarcastic and he's also the most romantic person I think I've ever met. He's so thoughtful," Caelynn boasted.
"So I think that's a big misconception -- that I'm, like, more invested in the relationship or he, like, doesn't treat me right. I'm like, 'No, he treats me exceptionally well and he's always going out of his way to just surprise me and do romantic things.'"
Caelynn also told HollywoodLife around that same time how she could see Dean and herself getting engaged and having a secret wedding, without anyone knowing.
"We've talked about keeping things super private and intimate," shared the former beauty pageant queen. "Also, maybe we don't need to get married. I don't know. Our relationship works so well, we go back and forth."
The happy couple made an appearance on Season 7 of Bachelor in Paradise last summer to give the season's new couples relationship advice, and the show's producers apparently suggested Dean should pop the question while in Mexico since it's where the pair had met and begun dating in Summer 2019.
Dean, however, wasn't interested at the time.
Once Dean and Caelynn took their relationship from Paradise and into the real world, they began traveling together and enjoying "the van life."
But the couple decided to put down roots and live a more traditional life in 2021 by becoming homeowners in Summerlin, Las Vegas. They moved into their house in April 2021.
Prior to meeting on Paradise, Caelynn competed for Colton Underwood's heart on The Bachelor's 23rd season, and Dean had been on multiple The Bachelor spinoffs after initially appearing on Rachel Lindsay's season of The Bachelorette.
Dean previously gushed to Us his relationship with Caelynn is "monumentally different" from other women he's dated in the past. Dean was previously linked to Kristina Schulman, Danielle Lombard and Lesley Murphy from The Bachelor world alone.
"She's very intelligent and compassionate. I am able to be myself around her and she's able to be herself and that's how we create synergy and build around each other," Dean explained of his love.
"For the first time in my Bachelor franchise relationship history, I feel like I'm able to say what I want, do what I want, and allow my partner to build with me while I'm doing that."
"She does joke around about us getting married all the time, and I always say, 'Sorry, it's not going to happen.' I don't know, I'm super unconventional and she obviously is a little more conventional," Dean told the magazine at the time.
"We joke around about it. Just try to keep expectations to a minimum, you know? Like I said on the show, underpromise, overdeliver."
It appears Dean has been overdelivering ever since!