"I know when I'm doing it and where I'm doing it," Dean said, according toUs Weekly.
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."
Dean reportedly announced back in June that he and Caelynn had already begun looking at engagement rings -- but the shopping adventure quickly turned into a sour experience.
Dean joked about how he was trying to convince Caelynn to choose a smaller diamond than the 4.5-karat rock she had been hoping to receive.
Dean admitted he had thrown a "hissy fit" at the time, recalling, "I was like, 'I don't even want to be in here right now. I don't really care what I wear on my finger, blah, blah, blah.'"
Dean said he and Caelynn "had a bit of a scuffle" and it's "such a touchy subject" in their relationship.
"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," Dean explained.
However, the pair managed to compromise, with Dean revealing, "I made a deal with her. I was like, 'I'll buy you a ring if you buy me a truck.'"
Dean added how they "basically are married" already because they have a joint bank account for house stuff.
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Caelynn opened up about the idea of proposing marriage to Dean in April. If she follows through with Dean's request to take the reins, she'll be following in The Bachelorette alum Becca Kufrin's footsteps.
"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.
"It's funny, I don't think a single person thought we were going to last and even we were like, 'No, I don't know what's going to happen here.' So, we definitely defied the odds," Caelynn gushed to Us ahead of the couple's two-year anniversary in June 2021.
"I think that's just our unique relationship and we really try not to listen to it. When you go on the show, so many people are going to have so many opinions about your relationship --good and bad. 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.
"When we were down there, the producers -- they, like, pulled me aside and they're like, 'Hey, Dean, you should totally propose to Caelynn on the last day of the show,'" Dean recalled on his podcast in October 2021.
"I was like, 'Are you serious? You're telling me this literally the day before we were supposed to go down and film this episode,'" Dean shared.
"The producers are not bashful when it comes to trying to encourage people to propose."
Dean and Caelynn began their relationship in the real world by traveling together and living "the van life," but they decided to put down roots and live a more traditional life in 2021.
In fact, Dean and Caelynn became homeowners in Summerlin, Las Vegas, and moved into their house in April 2021 after traveling constantly.
Dean previously summed up his relationship with Caelynn as "opposites attract," saying they both bring out positive traits in each other and are "both fortunate" it just works.
Caelynn and Dean's relationship seemed to move in a serious direction in late 2019 after the former beauty pageant queen stayed by Dean's side when he was hospitalized in the Swiss Alps following a serious skiing accident.
Caelynn apparently traveled to Switzerland to pick Dean up from the hospital and take care of him as he recovered from a dislocated hip, fractured femur, and surgery that required four screws to be put inside his body.
Dean and Caelynn found each other in Paradise after she competed for Colton Underwood's heart on The Bachelor's 23rd season. 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."
"That's never going to happen," Dean told Us at the time.
"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."
"We joke around about it," he added. "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!