Bachelor Nation’s Dean Unglert and Caelynn Miller-Keyes’ Relationship Timeline

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Bachelor Nation’s Dean Unglert and Caelynn Miller-Keyes’ Relationship Timeline

Dean Unglert and Caelynn Miller-Keyes have been dubbed a Bachelor success story, but their relationship got off to a rocky start. Unglert returned to Bachelor in Paradise for season 6 during the summer of 2019 after he found himself in the middle of a messy love triangle on season 5. During his second stint on the beach, he met Miller-Keyes, who was the one wrapped up in that summer’s drama. “A long time ago, when we first started dating, there were things where I was, like, disappointed about or just upset to hear, you know what I mean, about Caelynn’s dating history,” Unglert admitted to the former Miss North Carolina on his “Help! I Suck at Dating” podcast in November 2020. “And I was like, ‘Well, dude, if you were to flip it around and put me in the same position that I’m putting her in, I would look 20 times worse.’" He added, "So I’m not gonna sit here and be a hypocrite and be upset about something that she might or might not have done while I have done the same thing, if not worse, 10 times over.” During season 6 of BiP, fans learned Miller-Keyes hooked up with Blake Horstmann at Stagecoach before filming began. She called him out on the show, revealing he slept with her and their costar Kristina Schulman at the music festival. Horstmann subsequently tried to clear his name by sharing his texts with Miller-Keyes. [jwplayer LJ16s6RD-zhNYySv2] Unglert publicly defended Miller-Keyes when the show was airing. “I don’t think that you should ever really hold your significant other accountable for the things that they did before they knew the person that they’re dating,” he said on the podcast. “You could spend time thinking about it and dwelling on it, but you’re just gonna make yourself angry for literally no reason at all because it’s like, what are you supposed to do about someone doing things before they ever possibly knew you?” Miller-Keyes agreed, “It’s like, ‘That was before me, I don’t care, I don’t need to know’ kind of thing.” After a messy summer, Unglert and Miller-Keyes left the beach together — and they're still going strong. In October 2022, Us Weekly confirmed the duo's engagement after three years together. Scroll through for their timeline: [podcast_block]

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June 2019

Unglert and Miller-Keyes hit it off when he joined during week 2 of Bachelor in Paradise season 6.

Credit: ABC/Paul Hebert

June 2019

A few episodes in to BiP, Unglert left the beach, leaving Miller-Keyes heartbroken on her birthday.

“Our lifestyles are not going to be compatible coming out of this. And I don’t want to give you something that isn’t going to make you happy,” he told her on the show. “I just think that you deserve someone better than me, to be perfectly honest.”

The Bachelorette season 13 alum returned during week 5 to ask Miller-Keyes to leave the beach with him. While she went on a date with Connor Saeli after Unglert’s exit, the former pageant queen picked Unglert.

Credit: Courtesy Dean Unglert/Instagram

October 2019

Unglert and Miller-Keyes proved skeptics wrong as she embraced his lifestyle of living in a van.

Credit: Sara Jaye Weiss/Shutterstock

December 2019

A month after Miller-Keyes told Us Weekly that marriage could be in their future, Unglert told Us in December 2019 that he never wants to tie the knot.

“She does joke around about us getting married all the time, and I always say, ‘Sorry, it’s not going to happen,’” he told Us. “I don’t know, I’m super unconventional and she obviously is a little more conventional. We joke around about it. Just try to keep expectations to a minimum, you know? Like I said on the show, underpromise, overdeliver.”

Credit: Courtesy Caelynn Miller-Keyes/Instagram

February 2020

Not long after Unglert’s quotes about marriage made headlines, he was spotted wearing a band. The couple’s friends Ashley Iaconetti and Jared Haibon told Us at the time that they didn’t even know whether the pair had secretly wed.

“Dean had the reputation of being the F boy and not wanting to be in a committed relationship. And maybe some of that was a little bit true, which Dean has expressed many, many times,” Haibon told Us in April 2020. “He cares about Caelynn so much. And I think the ring is symbolic … Saying, ‘Hey, you know, I know I have a pass, but I’m here for you. I want to be with you. And that’s why I’m wearing the ring because I want to show you that. I only want to be with you. I don’t even want I don’t want to just say I want to show you.’”

Credit: Courtesy of Caelynn Miller-Keyes/Instagram

June 2020

Unglert and Miller-Keyes celebrated one year — and the anniversary of him dumping her on her birthday — in June 2020. Later that month, they finally revealed the truth behind their decision to wear jewelry on their respective ring fingers.

“I’m committed to Caelynn and only Caelynn. And that’s why I’ve been wearing it for the past six or so months,” he said on an episode of The Bachelor: The Greatest Seasons — Ever! “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 thing where you can wake up in the morning and see your partner wearing that ring and be like, ‘OK, yes, they know that I’m committed to them and vice versa.”

Miller-Keyes added, “He started wearing a hair tie around his ring finger, just to fight women off. … And I liked the idea. And then we just talked about getting rings. It’s just nice to know that we’re in a strong, committed relationship without necessarily having to get the government involved, as Dean likes to say.”

Credit: Courtesy Caelynn Miller-Keyes/Instagram

August 2020

“It’s always kind of tricky coming out of the show right away because you're agreeing to date someone that you don't really know that well. And so for the first month or two or three, even we're like still learning a lot about each other and still figuring out if it's actually going to be a relationship that works,” Unglert told Us in August 2020. “But once you kind of get past that initial, like, difficult hump, everything got really, really good for us. And I mean obviously, with quarantine and everything, it's been challenging as well. Like everyone has their own challenges with quarantine. …  It's a nice test to see that the relationship is as real as you thought it was.”

Credit: Courtesy of Caelynn Miller-Keyes/Instagram

April 2021

The reality stars took their relationship to another level when they moved into their brand new Las Vegas house in April 2021.

“We are officially homeowners!!! 🏠,” Miller-Keyes wrote at the time, sharing photos of the couple embracing in their kitchen.

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April 2021

Unglert rang in his birthday with a skydiving adventure that required some help.

"Kissing my 20’s goodbye 😘" Unglert captioned an Instagram video of the couple kissing before Miller-Keyes pushed him off a mountain on April 2021.

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May 2021

Unglert surprised his girlfriend with a date that had a lot of meaning behind it.

"Yesterday Dean surprised me and took me back to where we had our first date two years ago 🥰," Miller-Keyes captioned a photo of the pair via Instagram in May 2021.

Credit: Courtesy of Caelynn Miller Keyes/Instagram

September 2021

The pair jetted off to Greece for a romantic getaway, which included drinking wine at sunset, swimming in pools overlooking the ocean and wandering the streets.

Credit: ABC/Craig Sjodin

October 2021

Unglert revealed during an episode of his “Help! I Suck at Dating” podcast that producers suggested he propose to Miller-Keyes when they traveled to Mexico to give advice to the couples during the finale of season 7 of BiP.

“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,'” he recalled. "The producers are not bashful when it comes to trying to encourage people to propose.”

Credit: Sara Jaye Weiss/Shutterstock

November 2021

When talking about marriage on his “Help! I Suck at Dating” podcast, Unglert made it clear he had no plans to get down on one knee. “I don't know if she's speaking for me or if she's saying that she's going to propose to me," he said. "I've made it pretty clear to her. I was like, 'If you really want to get married, you should be the one proposing to me,' so I think she's got something in the works for that."

Credit: Courtesy of Caelynn Miller-Keyes/Instagram

February 2022

Unglert hinted that he was more open to the idea of marriage down the line, explaining on an episode of his “Help! I Suck at Dating” podcast, “If and when Caelynn and I put pen to paper, we are going to change our names. But we’re both going to change our last names.” The host, who previously looked into changing his last name to honor his late mother, noted he and Miller-Keyes both agreed to the last name “Bell,” his mom’s maiden name.

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April 2022

Miller-Keyes talked about the idea of proposing to Unglert during a YouTube Q&A. Although the Bachelor Nation alum admitted she initially thought her beau suggested the role reversal "for a reaction," she came to love the idea.

"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,'" she explained.

Miller-Keyes added, "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.”

Credit: Courtesy of Caelynn Miller-Keyes/Instagram

June 2022

Unglert revealed that he and Miller-Keyes had begun looking for engagement rings but had "a bit of a scuffle" over the particulars.

"It's such a touchy subject," the University of Colorado alum said on an episode of his "Help! I Suck at Dating" podcast. "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."

Unglert added that he and Miller-Keyes "basically are married" as they have a joint bank account. "We still have our separate accounts ... but we have a joint account we both put money in for house stuff," he explained.

Credit: Courtesy of Caelynn Miller-Keyes/Instagram

October 2022

Unglert teased during an episode of "Help! I Suck at Dating" that he and the former pageant queen would be engaged by the time the podcast aired, revealing that he had to use a placeholder ring after losing the original rock. "I wasn't planning on sharing that little piece of information today, but you guys got it out of me," he joked.

Us confirmed the duo's engagement after the episode was released.

After the engagement, Unglert recounted the proposal story during another episode of his podcast, revealing that Miller-Keyes was not very happy with him on the big day. The pair were in the middle of a "scary" 11-hour hike, and she didn't know he was planning to pop the question. "Caelynn was very angry at me for taking her there. She asked if we could turn around 55 times," Unglert recalled. "She was crying. She was angry. She was cursing at me, but she stuck with it and she eventually finished it."

Credit: John Salangsang/Shutterstock

December 2022

The engaged couple hit the red carpet before rocking out at iHeartRadio Jingle Ball in Los Angeles.

Credit: Courtesy of Caelynn Miller-Keyes/Instagram

December 2022

“According to Dean we’re now officially engaged! A while ago we agreed we would both propose to each other,” Miller-Keyes wrote via Instagram on December 14. “I had a lot of ideas on how I would do it, but after Dean had me conquer my fear of heights before his proposal, I thought it would be fitting for him to conquer his only fear, horses. I can’t wait for a lifetime of pushing each other out of our comfort zones 🙃.”