Dean, 31, previously revealed of potentially proposing marriage to Caelynn on his "Help! I Suck at Dating" podcast, "I made a deal with [Caelynn]. I was like, 'I'll buy you a ring if you buy me a truck.'"
And Caelynn, 27, took to her Instagram Stories on Monday and posted a photo of a Toyota vehicle's steering wheel. She appeared to be driving the car home.
"I spent the afternoon at Toyota picking up something special for Dean," Caelynn wrote on the image. "If you listen to 'Help I Suck at Dating,' you know what this is."
Dean raised eyebrows when he made the remark about demanding a truck in exchange for an engagement ring on his podcast in June.
Dean admitted at the time how he even threw a "hissy fit" upon seeing the 4.5 karat ring Caelynn is hoping to have on her finger one day.
"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'... We had a bit of a scuffle."
Dean said getting engaged is 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."
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. And that's why I've been wearing it for the past six or so months," Dean said on The Bachelor: The Greatest Season -- Ever! special that aired in June 2020.
"It's our way of telling the world or the people that we're around that we're committed to each other. I think it's one of those comforting things where you can wake up in the morning and see your partner wearing that ring and be like, 'Okay, yes, they know that I'm committed to them and vice versa.'"
Dean and Caelynn are apparently proud to still be together, considering most Bachelor Nation fans probably didn't think they'd make it.
"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 shared 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.'"
"The producers are not bashful when it comes to trying to encourage people to propose," he added.
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.
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.
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 Us 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!