Caelynn insisted Dean's lifestyle pushed her out of her "comfort zone" and her former "pageantry, perfected, robotic ways."
But Dean apparently got the van life out of his system because the couple moved into a home together in Las Vegas, NV, in Spring 2021. Caelynn also revealed they're planning a move to Denver, CO, in the future.
Dean and Caelynn are now focused on wedding planning, with Caelynn telling E! News, "It's such a unique time in our lives and everyone I know that's now married says, 'Just enjoy this moment.'"
"We're in this blissful time where we just love each other so much," Caelynn gushed.
"We're excited for the rest of our lives. I can't believe it happened because of reality TV. It's pretty wild."
Dean ended up popping the question with a temporary engagement ring with a "small" diamond because he claimed on his "Help! I Suck at Dating" podcast 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 earlier this month.
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, 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."
"I made a deal with [Caelynn]. I was like, 'I'll buy you a ring if you buy me a truck,'" Dean said, which sparked criticism from some fans that Dean didn't treat Caelynn very well.
Dean also admitted at the time how he had thrown 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."
That same month, Dean told Jared Haibon on their 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 planned to propose marriage in their own way, but his money was on him 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.
When Dean and Caelynn do tie the knot, they both plan to change their last names to "Bell" in honor of Dean's late mother, whose maiden name was Bell.
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.
One year later, Caelynn told Us Weekly 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.'"
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.
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!