Dean Unglert and Caelynn Miller-Keyes' Relationship Timeline

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It seems like Dean Unglert and Caelynn Miller-Keyes really are a match made in paradise.

The duo first met in 2019 while competing on Bachelor in Paradise. Although their time on the show was tumultuous, and even involved a breakup, Unglert and Miller-Keyes eventually left the show as a couple in June 2019. Over the span of their three-year relationship, the couple have traveled the world, lived out of a van, adopted two senior dogs, Pappy and Alastor "Mad-Eye" Moody, and gotten engaged.

Unglert and Miller-Keyes' relationship hasn't followed the traditional route of Bachelor Nation couples — which usually involves an on-screen proposal and a Neil Lane diamond ring — but they have proven skeptics wrong. Although Unglert was famously opposed to marriage and often said so on his podcast, Help! I Suck at Dating, he has warmed up to the idea throughout his relationship with Miller-Keyes. In June 2022, months before announcing their engagement, Unglert said that the duo "basically are married."

From meeting on the beach on Bachelor in Paradise to planning a wedding, here's everything to know about Dean Unglert and Caelynn Miller-Keyes' relationship timeline.

June 2019: Dean Unglert and Caelynn Miller-Keyes meet on Bachelor in Paradise

Caelynn Miller-Keyes Instagram

Unglert and Miller-Keyes first met on Bachelor in Paradise in June 2019. As soon as Unglert entered the beach during week two, the pair hit it off and quickly developed a solid foundation for a relationship.

June 15, 2019: Dean Unglert breaks up with Caelynn Miller-Keyes

Unglert broke up with Miller-Keyes on her birthday in June. "I know I won't be able to get where you would need me to be by the end of this," he told her, explaining his decision to leave the BiP beach. After he left, Miller-Keyes started spending more time with another contestant Connor Saeli.

June 2019: Dean Unglert returns to BiP and asks Caelynn Miller-Keyes to leave with him

After breaking up with Miller-Keyes and leaving the show, Unglert made a shocking return to BiP to ask Miller-Keyes to leave with him. "When I left, I made a decision that I thought was best for you, but it wasn't really fair of me to make that decision," he told her. "Then I flew back to San Diego, and the entire flight back I literally could not stop thinking about you. I rented a car and drove to the Grand Canyon, and as I was there I thought about how badly I wished that you were there with me."

Miller-Keyes responded saying that they had "something special and passionate" but his departure was confusing. Unglert continued, "I knew that I needed to come here and tell you that I wanted us to try and be in a relationship ... I came here to ask you if you would leave Paradise with me today." Though Miller-Keyes was hesitant to leave and dump Saeli, she eventually agreed to leave the beach with Unglert.

July 2019: Rumors of Dean Unglert and Caelynn Miller-Keyes' relationship begin spreading

Caelynn Miller-Keyes Instagram

Rumors of Unglert and Miller-Keyes' relationship began before season 6 of BiP aired in August 2019. In July, a source told PEOPLE, "They both went to Paradise and really hit it off there, but then Dean got cold feet and left. He got home and realized he really had feelings for Caelynn, so went back to Paradise for a second chance."

The insider continued, "Things have been going much better between them since they left Mexico together."

August 2019: Dean Unglert says Blake Hortsmann "slut-shamed" Caelynn Miller-Keyes

When Bachelor in Paradise aired in August, viewers saw that Unglert and Miller-Keyes' journey wasn't exactly drama-free. While on the beach, Miller-Keyes and Blake Horstmann's hookup at the Stagecoach Country Music Festival became a major source of drama. As the show aired, Horstmann shared private texts between himself and Miller-Keyes in an attempt to clear his name. In the messages, Horstmann wrote, "we can cuddle but no sex lol," and Miller-Keyes replied, "Yes sex" and "Only sex."

During an episode of Almost Famous, a podcast hosted by fellow Bachelor alums Ben Higgins and Ashley Iaconetti, Unglert called Horstmann out for sharing the screenshots. "It's an obvious form of slut-shaming," he said. "Now Caelynn's parents and her sisters and her friends are going to have to see these messages … it's nonconsensual from her part."

September 10, 2019: Dean Unglert and Caelynn Miller-Keyes confirm their romance

Dean Ulgert Instagram

Unglert and Miller-Keyes confirmed they were still together and enjoying van life post-Paradise by going Instagram official on Sept. 10, 2019. "Lots of ramen, very few showers, and a whole lot of happiness," Miller-Keyes captioned her post. Unglert wrote, "Sorry we had to leave #bachelorinparadise early, the vantasy suite waits for no one."

October 2019: Caelynn Miller-Keyes says Dean Unglert made her a better person

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In October 2019, Miller-Keyes opened up to PEOPLE about her romance with Unglert. "It's been great," she said. "We're getting to know each other. We've been traveling a lot. Traveling the world with someone is a great way to get to know them."

She added, "He brings out the best side of me. He just makes me a better person. And I'm so happy."

December 2019: Dean Unglert says he isn't proposing to Caelynn Miller-Keyes yet

Unglert has been happy to take his time with his romance with Miller-Keyes. In December 2019, he told PEOPLE that they were being "super patient" with their romance. "There's no, like, impending engagements or anything like that. We understand that with the Bachelor franchise, you kind of get put in a pressure cooker with your relationship and we're just traveling together, exploring each other, and having fun and doing what we're doing."

However, he thought Miller-Keyes had a different view. "She might tell you otherwise but it seems like, you know, we're on a good path at the moment and there's nothing really on the horizon but I think that's kind of the best," he said. "You don't really set like relationship goals until later on down the line, so we'll see."

However, Miller-Keyes seemed to agree with Unglert, adding that she didn't "want to rush anything." She explained, "We're at such a good place right now. We'll move in together when the time is right, but I don't want to rush anything and I don't want it to be contingent on a lease ending or something like that. But maybe. Maybe next year. Maybe in 2 years. Who knows."

January 2020: Dean Unglert thanks Caelynn Miller-Keyes for taking care of him after his skiing accident

Dean Ulgert Instagram

Unglert had a scary skiing accident in the Swiss Alps in January 2020. Fortunately, Miller-Keyes was there to take care of him. Unglert thanked his "primary caretaker" on Instagram after the incident.

"Back in the states after an unfortunate turn of events in Europe," he wrote. "It would have been a whole lot worse without my primary caretaker there to change my smelly socks, carry my luggage, and keep me entertained."

Unglert added, "Thank you for everything you've already done and for everything you still unwittingly have to do."

February 2020: Dean Unglert and Caelynn Miller-Keyes spark marriage rumors

Caelynn Miller-Keyes Instagram

On Valentine's Day 2020, a fan commented, "Get married!" on Miller-Keyes' post for Unglert, and Miller-Keyes had an interesting response: "We already did." Friend and BiP alum Iaconetti added to the speculation when she explained, "[Unglert] keeps saying that they got married when they were in Europe and he broke his leg and I'm thinking that possibly really did happen."

That same month, Jared Haibon told PEOPLE, "Every time we ask [Unglert and Miller-Keyes], he says it with a grin — he's like, 'We're married.' " It looks like the duo was just stirring the pot, though, as they never officially confirmed wedding rumors.

June 2020: Dean Unglert and Caelynn Miller-Keyes explain their commitment rings

Unglert has openly talked about his unease about marriage. Rather than getting engaged, the duo got commitment rings to cement their relationship. "In my opinion, I don't need the title of husband to show the world that I'm committed to one person," Unglert told host Chris Harrison during an episode of The Bachelor: The Greatest Seasons — Ever!. "The fact that I'm wearing the ring is showing that I'm committed to Caelynn and only Caelynn, and I've been wearing it for the past six or so months."

He explained that they were in a "domestic partnership," adding, "She wears her fun little ring as well, which isn't the traditional ring of marriage or engagement ring, but it's our way of telling the world and the people we're around that we are committed to each other."

Miller-Keyes explained how the rings started. "He started wearing a hair tie around his ring finger to fight women off. I liked the idea, and we just talked about getting rings," she said. "It's just nice to know we are in a strong committed relationship without necessarily having to get the government involved as Dean would like to say."

June 15, 2020: Dean Unglert and Caelynn Miller-Keyes celebrate their breakup anniversary

The couple didn't exactly start off on the right foot when he broke up with her in Paradise. One year later, they were able to poke fun at the situation. "Happy one year anniversary of the day you dumped me 😘," Miller-Keyes quipped on Instagram.

In his post for Miller-Keyes' birthday, Unglert also referenced their beach breakup. "This time last year, some jerk was breaking up with her on a beach in Mexico. Hopefully this birthday goes a little smoother for @caelynnmillerkeyes," he wrote.

January 2021: Dean Unglert and Caelynn Miller-Keyes buy a house together

Caelynn Miller-Keyes Instagram

In January 2021, Unglert and Miller-Keyes bought a house together in the Summerlin neighborhood of Las Vegas. They had the home built, so they didn't move in until April 2021. "Caelynn and I just bought a house out in Vegas," Unglert said during an episode of his podcast. "We know it's an older community, which I think is good. We're not trying to be in the sinning part of the city, but yeah we're excited."

March 2021: Dean Unglert opens up about "unconditional love" with Caelynn Miller-Keyes

Caelynn Miller-Keyes Instagram

During an episode of Help! I Suck At Dating with Haibon, Unglert opened up about the "unconditional love" he feels from Miller-Keyes. "I can be my dirtiest, grungiest self — doesn't matter," he explained. "She still loves me and accepts me and appreciates me for being that. I think that's the biggest thing."

Unglert continued, "Unconditional love is a big part of it. I think I've had that before, but I've never been able to fully receive it until just recently."

August 2021: Dean Unglert says he and Caelynn Miller-Keyes don't use the word "love"

In an episode of his podcast, Unglert opened up about an unusual nickname Miller-Keyes has for him. "She calls me Maka, but that's, like, something that I made up and then she ran with it," he said. "I just hate saying the L-word word, so I was like, 'Let's make up a different word, so we don't have to say that to each other all the time.' "

August 2021: Dean Unglert calls Caelynn Miller-Keyes "suffocating" and then apologizes

Unglert and Miller-Keyes' relationship got flack after he called her "the most suffocating" woman he'd ever dated. The conversation came up during an episode of his podcast after a listener asked about feeling that way in their relationship. Unglert clarified, "I actually kind of enjoy it, so it's nice."

In September 2021, Unglert apologized for the poorly chosen adjective. "It's a horrible word, don't get me wrong," he explained. "It's the wrong adjective to use to describe anyone in a relationship. I was simply saying that in past experiences, I would hate to be suffocated, but with Caelynn, although my instinct is to say, 'Don't suffocate me,' in reality, I'm like, 'You can suffocate me because I enjoy spending time with you' sort of thing."

September 2021: Dean Unglert and Caelynn Miller-Keyes talk about getting married in Italy

During a trip to Italy's Lake Como, Unglert warmed up to the idea of getting married to Miller-Keyes.

"It's very, very beautiful out there," he shared on his podcast. "And it's funny because a lot of the people that we ran into — like, we're just, you know, Caelynn and I are just a couple on vacation — they're like, 'Oh, you guys are here for your wedding [and] for your honeymoon.' [We're] like, 'No. Like, we're just here because we've always wanted to visit.' And they're like, 'Oh, you got to come back, like, for your wedding.' It definitely is a place where a wedding would be spectacular. It's just, like, one of the most beautiful places we've ever visited."

He continued, "You can't help but be like, 'Oh, my gosh. This is amazing. I want this to be the rest of my life. And since I'm here, like, I want you to be in my life for the rest of my life,' which I always thought those things, obviously."

Apparently, the duo also talked about a hypothetical Italian wedding. "Obviously, super major hypothetical, she's like, 'Who would you invite? Like, who would you bring?' Blah blah blah," he said. "It's like, 'I probably wouldn't bring anyone. You know, like my family. Maybe that's it.' "

October 2021: Dean Unglert says producers wanted him to propose to Caelynn Miller-Keyes during BiP cameo

Craig Sjodin/ABC

When Unglert and Miller-Keyes made a cameo on season 7 of Bachelor in Paradise, the producers hoped Unglert would take the opportunity to propose. In October 2021, he explained the situation on an episode of his podcast. "When we were down there, the producers … they pulled me aside and they were, like, 'Hey Dean, you should totally propose to Caelynn on the last day of the show,' " he recalled. "I was like, 'Are you serious? You're telling me this, like, literally the day before we're supposed to go down and film this episode?' "

Unglert continued, "All that's to say the producers are not bashful when it comes to trying to encourage people to propose."

November 2021: Dean Unglert says Caelynn Miller-Keyes should propose to him

He has made no secret of hesitating to get down on one knee. In November 2021, he explained on his podcast that he thinks Miller-Keyes should be the one to propose.

"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, which I think is pretty cool. Maybe we can do, like, a dual thing," he told his co-host. "I guess it's kind of one of the negatives about going to all of these weddings is it gets your girlfriend in a mood to get married. I guess give us 12 months, 12-13 months and we'll have something more formal on the books."

During a YouTube Q&A, Miller-Keyes explained that she wasn't opposed to 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.

November 29, 2021: Dean Unglert and Caelynn Miller-Keyes mourn their dog Pappy

Unglert and Miller-Keyes adopted their senior dog Pappy together in February 2020. Unfortunately, Pappy passed away in November 2021. The couple shared the sad news in a joint Instagram post. "​​Today was one of the hardest days of our lives. Today our sweet little man left our earth. He took his final breaths in the arms of his loving mother," they captioned the post, a video compilation of Pappy's life with them.

January 11, 2022: Dean Unglert and Caelynn Miller-Keyes adopt their dog Alastor Moody

Caelynn Miller-Keyes Instagram

The couple adopted another senior dog in January 2022. Sharing the news on Instagram, Miller-Keyes wrote, "​​We're back to being dog parents. Meet Alastor Moody."

In March 2022, Unglert shared photos of their pup, who is named after the Harry Potter anti-hero Alastor "Mad-Eye" Moody. Unglert wrote, "We're looking forward to bringing this old man the best years of his life, and grateful for the joy and happiness he brings us along the way too!"

June 2022: Dean Unglert and Caelynn Miller-Keyes celebrate their third anniversary

Caelynn Miller-Keyes Instagram

In June 2022, Unglert and Miller-Keyes celebrated their third anniversary. Unglert posted a sweet video for the occasion, writing, "Three years doesn't seem like much when you've got forever left to go."

Miller-Keyes also celebrated the milestone on Instagram. "Every year gets better and better. Here's to 3 years with you @deanie_babies."

August 29, 2022: Caelynn Miller-Keyes hints at an upcoming engagement to Dean Unglert

Miller-Keyes teased potential engagement news on her Instagram Story, writing over an image of a steering wheel, "I spent the afternoon at Toyota picking up something special for Dean."

The gift of a new car could mean big news for the Bachelor Nation couple as Unglert had previously said on a June 2022 episode of his podcast, Help I Suck at Dating, "I made a deal with her. I was like, 'I'll buy you a ring if you buy me a truck.' "

Miller-Keyes hinted at the deal, writing, "If you listen to Help I Suck at Dating you know what this is," at the bottom of the photo.

September 8, 2022: Caelynn Miller-Keyes says she and Dean Unglert may elope

The Bachelor alum confirmed to PEOPLE that Unglert got her a ring but said they're "not engaged" yet. The couple have "got something coming," she added.

"I haven't seen it," she continued. "I just know he has it. He's very open." She also shared that she's having Unglert's ring made.

Miller-Keyes said that their engagement will be a non-traditional one. "We're also both proposing to each other because partnerships are supposed to be equal," she said. "I'm proposing to him, having the day all about him, and he's proposing to me. We're very non-traditional. It's all about equality in our relationship."

Once engaged, Miller-Keyes revealed the pair are considering a quick wedding. "I think we just want to elope," the model shared. "We recently went to his brother's wedding where they engaged and then married the next day. It was solely about their love, so we just want to focus on our love, and it just be about that and nothing like … extraordinary."

October 25, 2022: Dean Unglert and Caelynn Miller-Keyes get engaged

A source confirmed to PEOPLE in October 2022 that Miller-Keyes and Unglert were officially engaged. The news came after Unglert spoke about his proposal plan during an episode of his Help! I Suck at Dating podcast. In the episode, he revealed that he got a "new" placeholder engagement ring for Miller-Keyes after losing the original ring, a 4.5-carat emerald-cut diamond.

"It might be in the garage somewhere but yeah, moral of the story is don't put your engagement rings in the junk drawer," he said. "So I did have to go out and buy a placeholder ring for now, but it's not quite as nice as the first one was."

The Bachelor in Paradise alum then revealed that a proposal was imminent, saying, "It'll happen by the time this podcast airs," he said. "Maybe. Maybe the day after it airs."

Co-host Haibon then suggested not dropping the episode "until we know" for sure. To which Unglert confirmed that "it won't" air before the proposal actually goes down.

October 30, 2022: Caelynn Miller-Keyes says she and Dean Unglert both plan to change their last names when they get married

"We'll both be changing our last name to Bell," Miller-Keyes told fans during a Q&A on Instagram. She went on to explain that Bell is Unglert's mom's maiden name. His mom, Debbie, died in 2006 from breast cancer.

October 31, 2022: Caelynn Miller-Keyes was "very angry" with Dean Unglert just before he proposed

It took the couple two days to hike to the place where Unglert proposed in Hawaii. On his podcast, Help! I Suck at Dating, the reality star shared that Miller-Keyes was "very angry" with him for bringing her on the 11-mile trek that "people die on semi-regularly."

Unglert said that his now-fiancée threatened to turn around multiple times.

"Eventually I just started saying, 'Yeah, let's turn around. If you want to turn around, let's turn around.' But she didn't, I mean, credit to her because she was crying, she was angry, she was cursing at me," he said. "But she stuck with it and she eventually finished it. So, yeah, it was a trying experience."

The hike concluded on a stunning (and secluded) beach on the island of Kauai — the spot where Unglert got down on one knee.

"The hardest and scariest hike I've ever done led to the best day of my life," Miller-Keyes wrote on Instagram.

January 16, 2023: Dean Unglert says he'd marry Caelynn Miller-Keyes at a courthouse

Amid planning their big celebration, Unglert told PEOPLE that he'd happily say "I do" at the courthouse to avoid "a stressful and painfully expensive" wedding.

"I really just want to go to a courthouse by ourselves, then just sign the papers," he said. "But we're having a big party. It'll be fun, I know it'll be fun. I just hate being the center of attention."

February 14, 2023: Caelynn Miller-Keyes permanently joins Dean Unglert's podcast as a host

Following his engagement to Miller-Keyes, Unglert rebranded his podcast with Jared Haibon and asked his fiancée to become a permanent host.

What was once Help! I Suck at Dating is now Help! We Suck at Being Newlyweds. The podcasting trio shared the big news on Instagram.

February 15, 2023: Dean Unglert and Caelynn Miller-Keyes announce wedding location

In February 20223, the couple announced they will tie the knot on a ranch in Colorado.

"I couldn't imagine a more perfect place to marry this perfect guy," Miller-Keyes captioned a sneak peek at their wedding venue on Instagram.