Dean reportedly spilled the story during a recent episode of his "Help! I Suck at Dating" podcast.
When Dean and Caelynn traveled to Mexico to film Bachelor in Paradise's seventh-season finale, Dean recalled, "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.'"
"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 continue to travel the world together and just enjoyed a romantic getaway to Greece last month.
But the pair seem ready to put down roots and live a more traditional life now.
In fact, Dean and Caelynn became homeowners earlier this year and moved into their new place in Summerlin, Las Vegas together in April after traveling constantly and living in Dean's van.
Dean and Caelynn fell hard for each other on Bachelor in Paradise's sixth season, which aired in Summer 2019.
"My wonderful boyfriend has made me kind of embrace the natural side of me and made me kind of accept myself without makeup... [Going] completely natural has been an adjustment, but it's been great to explore that too," Caelynn, a former Miss North Carolina USA, told Us back in the spring.
"No relationship can ever compare to the relationship we're in... He brings out this different side of me and he makes me more adventurous, and I just embrace different sides of me that I never had before."
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During a June 2020 appearance on The Bachelor: The Greatest Seasons -- Ever!, Dean and Caelynn opened up about how serious their relationship truly is, even though they haven't had a wedding or gotten married.
"Dean, I see a ring on your finger. I am going to ask you once and for all, for Bachelor Nation, are you guys married?" the franchise's former host Chris Harrison asked.
"Well, listen Chris, here's the thing. I don't think in my opinion -- I don't need the title of 'husband' to show the world I'm committed to one person," Dean said.
"And so the fact I'm wearing the ring is showing just that, that I'm committed to Caelynn and only Caelynn... I've been wearing it for probably the last six or so months."
Dean pointed out that Caelynn wears a "fun little ring as well," adding, "It's our way of telling the world -- or the people that we're around -- that we are committed to each other."
"And for her, too, I think it's one of those comforting things where you can wake up in the morning and see that your partner is wearing that ring," he explained. "And, yes, they know I'm committed to them and vice versa... We are in this for the long haul, there's no going back."
Caelynn added at the time, "It's just nice to know that we are in this strong, committed relationship without necessarily having to get the government involved, as [Dean] likes to say."
Dean 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 began dating on Bachelor in Paradise 6 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."
Dean, however, admitted in December 2019 he didn't think marriage would ever be in the cards for Caelynn and himself.
"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."