Dean proposed marriage to the former beauty queen in late October following a grueling 22-mile hike to Hawaii's Kauai Island about three years after they began dating on Season 6 of Bachelor in Paradise, which aired in Summer 2019.
"A friend told me, 'Enjoy every moment, enjoy the engagement, enjoy the wedding, don't rush anything.' So thankfully I listened to her because I was like, 'I wanna try on dresses, I wanna do all these things before I'm even engaged,' which is ridiculous," Caelynn, 27, explained to Us Weekly on its "Here for the Right Reasons" podcast.
"So thankfully I listened... and I waited," she added.
Caelynn said her self-restraint has made the current wedding-planning process even "more exciting" for her.
"We're in this really fun fiance phase and also we're getting to look at venues, we're getting to decide where we wanna get married. So it's been fun," Caelynn shared.
Caelynn and Dean have apparently settled on tying the knot in Colorado, although they had previously discussed a destination wedding abroad.
"We'd originally thought we'd elope in Italy... and then we [realized] we actually do want all of our friends there, so we're going get married in Aspen," Caelynn revealed.
"But then I was like, 'Maybe Bam, maybe here.' And he was like, 'I have my mind made up.' And when his mind is made up, you can't talk to him."
Caelynn continued, "And I was like, 'You don't understand that the wedding process is about a lot of decisions and changing things, so do I just not involve you?' And he was like, 'I don't know.' So, we'll see."
Caelynn said she has already picked out a dress for an engagement party and has "appointments scheduled" to try on wedding gowns for the big day.
"I would like two dresses," Caelynn noted, acknowledging how one dress would be for the ceremony and her second dress would be for the reception.
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"I keep thinking about... when I knew he was The One, when I knew we were gonna get engaged. I think we just kept talking about it and I kept joking about it. And I think the more I joked about it, the more he was like, 'Okay, maybe I could get married,'" Caelynn recalled.
"I don't know if that's what happened in his mind. But that to me is when it switched -- just easing the thoughts into him. But then we were like, 'Okay, we actually could get engaged, we could get married and this is something we want.'"
She added, "So I don't know if that was a year ago. I have no idea the timeframe, but we've been talking about it for a while -- both about proposing to each other and getting engaged."
On Bachelor in Paradise's sixth season, Dean broke up with Caelynn on her birthday and left the show alone because he didn't think he was ready to provide the commitment that Caelynn wanted.
However, Dean returned for Caelynn later on and begged her to give him a second chance, and the pair left Paradise dating each other.
Following their Paradise exit, Dean convinced Caelynn to live "the van life" with him in which they traveled together and didn't have a stable home base.
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 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.
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 to each other 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.
Dean and Caelynn have been wearing wedding bands since 2020 to show they are committed to each other. and so Caelynn told Us last year that 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."
Dean, however, believed in late 2019 that marriage was "never going to happen" for them.
"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!