Clare Crawley and Dale Moss' Relationship Timeline

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Even by The Bachelorette's standards, Clare Crawley and Dale Moss had a whirlwind romance.

The duo met in July 2020 while filming the show's 16th season. Only 12 days later, Crawley and Moss reportedly left the show as an engaged couple. At the time, the pair were confident in their relationship. "It's wild that we're here right now, but when you know, you know," Moss later explained. "This is how it was supposed to happen at the beginning. We saw this coming a long time ago." Crawley added, "We so saw this coming. I felt it. I knew it."

Crawley and Moss had many ups and downs over the course of their relationship — including some messy Instagram posts and one short-term breakup — before calling it quits for good in September 2021. "It's painful when you feel like somebody who you love deeply doesn't even have enough respect to take you to sit down and have a very vulnerable conversation and owning your stuff on both sides," Crawley said after the breakup. "It's hurtful because it's like, 'You think that little of me?' But yet he supposedly loved me … Maybe that is the closure."

From a first-impression rose to their breakup, here's everything to know about Clare Crawley and Dale Moss' relationship.

July 2020: Clare Crawley and Dale Moss meet

Craig Sjodin/ABC Clare Crawley and Dale Moss

Crawley and Moss met for the first time while filming The Bachelorette at La Quinta Resort & Spa in Palm Springs, California, after a four-month production shutdown due to the COVID-19 pandemic. They hit it off right away, and Moss even received Crawley's first impression rose.

July 2020: Clare Crawley and Dale Moss get engaged

Craig Sjodin/ABC

By the fourth episode, Crawley had set her sights on Moss and wasn't interested in exploring any other relationship. "I'm just so in love with the man that you are," she told Moss. "You made me feel like everything that I've ever been through, all the ups and downs and other relationships, it was all worth it because I've got you right now."

Moss shared similar feelings. "I want nothing more than to keep moving forward, to be there for you each and every day," he said. "And I thought a lot about my mother and what she would think about you and she would absolutely love you. And all she's ever wanted for me is someone who just loves me unconditionally and would be there for me no matter what."

The former football pro then proposed to Crawley. "And the best is yet to come. I'm not going anywhere. I want to make you happy each and every day," he said. "With that being said, I'm going to do it. I'm doing it. Clare, will you marry me?"

Crawley said yes before adding, "Put that ring on my finger. I've waited a lot of years for this."

November 6, 2020: Clare Crawley and Dale Moss open up about their engagement

Craig Sjodin/ABC Dale Moss and Clare Crawley

After their proposal episode aired, Bachelor Happy Hour released an episode where Crawley and Moss discussed their whirlwind engagement and addressed their critics. "I really get that I am not for everybody, I get that everybody might not do what I did or agree with what I'm doing, but at the end of the day, this is all for love," Crawley said.

Moss opened up about the proposal, explaining, "That portion was not nerve-racking for me. I felt so calm and so confident, and I knew exactly what I was going to say because I've run through that so many times."

November 2020: Clare Crawley and Dale Moss visit their hometowns

Four months after their engagement, Crawley and Moss introduced each other to their hometowns of Sacramento, California, and Sioux Falls, South Dakota. "I just gave Dale the ultimate tour of Sacramento the other day, and guess what we are doing today?" Crawley said on Instagram. "We're going to check out your old home, your high school! ... I guess you would call this the official hometowns!"

Crawley also got a chance to meet Moss' sister Robyn while visiting South Dakota.

December 25, 2020: Clare Crawley and Dale Moss spend their first Christmas together

Dale Moss/instagram Dale Moss and Clare Crawley

Crawley and Moss spent their first Christmas together in 2020, and they both celebrated the milestone on Instagram. "I pray that no matter what these holidays look like for you this year, you are able to share + feel the love regardless of circumstances! The greatest gift of all ✨ Merry Christmas!!" Crawley wrote alongside a photo of her kissing Moss.

Moss echoed her sentiment. "Wishing you all a Merry Christmas & sending nothing but love this holiday season," he captioned a photo of the couple in the snow.

December 29, 2020: Clare Crawley gives Dale Moss a haircut

The hairstylist and Moss took a major step in their relationship when she cut his hair for the first time. "Today is a monumental step in @clarecrawley & my relationship," Moss shared on Instagram. "Her first time ever cutting my hair and my last haircut of 2020!"

January 2021: Dale Moss says he only went on The Bachelorette for Clare Crawley

Clare Crawley/Instagram Clare Crawley and Dale Moss

In an interview, Moss opened up about his decision to go on The Bachelorette. "Now, I could have never planned what happened because I was nominated," he explained. "I never actually signed up. And I turned it down over, and over, and over again. And I actually finally committed to it four days before everyone was supposed to leave for the show. And the only reason I committed to it was because Clare was announced as Bachelorette at that time."

Moss continued by complimenting Crawley. "She was so confident and passionate about it," he said. "And I know that she had been through this before, but I felt by watching her that this was her time and she was exactly where she was meant to be."

January 19, 2021: Clare Crawley and Dale Moss break up

Later that month, Moss announced his and Crawley's breakup on Instagram. "I wanted [to] share with you all that Clare and I have decided to go our separate ways," he wrote. "We appreciate the love and support we've received from so many people, but this is the healthiest decision for both of us at this time."

He continued, "We strongly believe in leading with love and always remaining true to oneself - something our families have taught and instilled in us throughout our lives. We only hope the best things for each other."

January 21, 2021: Clare Crawley is "blindsided" by split from Dale Moss

After Moss' breakup post, Crawley claimed the decision wasn't really mutual. "I was made aware of a 'mutual' statement at the same time you all were, so I've needed some time to really digest this," she wrote. "Speaking for myself, my intentions with this relationship have always been very clear, so the truth is I am crushed."

A source told PEOPLE, "Clare feels blindsided by the split. She genuinely thought they could make things work and after everything she's been through, she can't believe she's in this place again."

February 16, 2021: Clare Crawley and Dale Moss are spotted together

One month after their breakup, Crawley and Moss were seen spending time together. First, they were spotted at a bar in Florida before taking a walk to the waterfront. A week later, a Bachelorette fan account shared an Instagram Story of Crawley and Moss cozying up by a resort pool.

April 2021: Clare Crawley and Dale Moss are "in a good place"

In April, Moss appeared on the podcast Hollywood Raw and explained how he reconnected with Crawley. "We've never hid throughout this entire time that we've been around each other," he said. "We are definitely taking time, and we're spending time together. Clare and I, we're in a good place. When the time is right we will definitely talk about all those things. For right now, we're just focused on one another."

He added, "We're keeping things private and that's working for us, in due time we'll speak about that together. ... We're just working through things and supporting one another and just taking it as it comes."

May 2021: Clare Crawley wears engagement ring on vacation with Dale Moss

In May, Crawley and Moss vacationed in Hawaii, and the former NFL player shared a photo on Instagram. In the picture, Crawley wrapped her arms around Moss — and she sported her engagement ring. "This makes me happy," Moss captioned the photo.

July 2021: Clare Crawley and Dale Moss are "on the same page"

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In July, a source confirmed to PEOPLE that Crawley and Moss were back on and doing well. "Clare and Dale took things really slowly when they got back together," the insider said. "They wanted to make sure they were on the same page. ... Clare is so happy that they're in this great place now. They're both excited about the future."

July 28, 2021: Clare Crawley and Dale Moss celebrate their 1-year anniversary

Dale Moss/Instagram Dale Moss, Clare Crawley

Crawley and Moss celebrated their first anniversary in July 2021. "Happy ONE YEAR Anniversary love!!" Crawley wrote on Instagram. Moss replied in the comments, "Love you with all my heart. Before we even met I knew god was working but never could have imagined what he had in store for us and there's so much more ahead. My heart is with you always ❤️."

Moss wrote his own tribute to Crawley. "It's the moments that nobody sees that make life and our love so special," he wrote. "The most beautiful thing is that those are the moments only we will carry forever. When we first met I knew god's hand was at work but I could have never imagined the journey he had in store for us. Love you with all my heart @clarecrawley."

September 2021: Clare Crawley and Dale Moss split again

The pair broke up again in September 2021. A source confirmed the split after the couple didn't appear to celebrate Moss' birthday together on Sept. 24. "It was mutual. It happened two weeks ago," the source told PEOPLE.

September 30, 2021: Clare Crawley addresses her split from Dale Moss

Crawley addressed her split from Moss on Instagram. "I hate that I even have to say this, but in response to all the questions that are coming my way right now… I'm choosing not to speak right now on the details of my relationship, because at the end of the day anyone can put on an ACT or throw words together to form any narrative they want," Crawley wrote.

She added, "What I will speak on is emotionally and physically I'm going through a lot with healing from my recent surgery still, and my mother being placed on hospice care now. So my energy is focused on grieving, healing and being present at home here in Sacramento while trying to share and help others going through similar life experiences as I'm sharing today."

Crawley concluded, "I am just thankful for the people in my life who offer genuine unconditional love with no personal gain, and stand by me through thick and thin ... actions speak for themselves."

October 2, 2021: Clare Crawley says she refuses to "stay down" after Dale Moss split

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The former Bachelorette opened up about her post-breakup healing process on Instagram. "It takes a lot to bring me to my knees ... But damn this week has pushed me to that point," she said. "One thing I refuse to do though is stay down. I'll be dammed if I let it all take me out, so amidst all this, I'm taking steps even if [they] are small. I will feed myself the right food, drink some water and handle it the best I know how."

October 4, 2021: Dale Moss addresses cheating rumors and breakup from Clare Crawley

A few days later, Moss addressed both the breakup and cheating rumors. "Dale and Clare broke up in mid September when Clare was in New York City spending time with him," Moss' rep said in a statement. "Clare then chose to fly home to Sacramento and asked Dale to send her things. A couple of weeks later, Clare's mother's condition worsened, and Dale chose to immediately fly out to Sacramento to be with her."

The statement continued, saying that Moss visited Crawley in Sacramento, left for L.A. for a work obligation and planned to return to Sacramento. Moss' rep then alleged that Crawley blocked and ghosted Moss.

"Dale has chosen not to speak publicly regarding all these reports because he wants to give Clare and her family the respect they need during this difficult time," the statement concluded. "He wishes Clare nothing but the best, and he is keeping her and her family in his thoughts and prayers."

October 2021: Clare Crawley reflects on split from Dale Moss

In an appearance on the podcast Whine Down, Crawley discussed her breakup and what she learned from their relationship. "If my biggest regret is trusting the process, trusting a man ... I don't think that that's a regret," she said. "I trusted somebody, I believed somebody that they were who they said they were or that they would hold up to the promises that they make when they get down on one knee. ... I loved, and have always had such a deep love for, Dale, and that a) he doesn't go away overnight, and b) I don't regret that. I loved loving him."

Crawley continued, "It can get very messy and very icky, and I always try to err on the side of taking the high road, even when there is a lot of things I could say. I wish people knew both sides, you know, because it's easy for a publicist or a source to put out a narrative of what they want their client or friend to look like and appear to, especially when your career is based ... on being in the public eye."

November 19, 2021: Clare Crawley says she found "peace" after Dale Moss split

In an Instagram Q&A, Crawley shared how she was faring after the breakup. After one fan asked what helps her to "be independent after a breakup," Crawley replied, "Focusing on my self care, healing and growth. No man can take that from me."

When another follower commented that Crawley looked "peaceful," she responded, "I have definitely found peace in so many ways so thank you! But life still has its things that I'm dealing with so don't get me wrong. I'm just choosing to help them and look at them ALOT differently. (a great therapist helps)."

December 14, 2021: Clare Crawley seemingly comments on Dale Moss' acting debut

In December, the trailer for Moss' acting debut — the rom-com Love, Game, Match — was released. One day later, Crawley seemed to shade her ex. "For the record, you guys can stop sending me all the acting reel clips," she wrote on her Instagram Story. "I had a front row seat to that since day one."

October 7, 2022: Clare Crawley gets engaged to Ryan Dawkins

In September 2022, Crawley went Instagram official with her boyfriend Ryan Dawkins. Dawkins, a CEO based out of Oakland, California, proposed to Crawley on Oct. 7. He popped the question during the lantern release at the RiSE Festival. "He has held me in my darkness, loves me through my healing, and we now celebrate the light together! The easiest YES of my life ❤️," she wrote on Instagram.

Crawley later opened up about the romantic proposal to PEOPLE. "I am over the moon! This was the last thing I expected right now, especially coming from where I was a year ago. It's just been a serious journey, and Ryan has been by my side since the very beginning," she explained.

Plus, according to Crawley, Dawkins isn't interested in fame. "Really what he's in it for is my heart, and he is so consistent and so vocal about how much he loves me. It is something I have never experienced," she said. "It's been such a gift having him in my life."

November 1, 2022: Dale Moss opens up about Clare Crawley's engagement

After learning the news of Crawley's engagement, Moss told Entertainment Tonight he's supportive of his ex's milestone. "Everyone deserves love and the goal is to find it," the Bachelorette alum said. "So whenever anyone can that's a great day."

January 11, 2023: Clare Crawley admits she was disappointed with Dale Moss' proposal

During an appearance on Bachelor Happy Hour, Crawley spoke about Moss' proposal, explaining that she was sad her ex wasn't able to involve her mother.

"I was so upset for so long at my previous relationship because I felt like 'You took that moment and that time away from me and my mom that was special, that I had been waiting to share with my mom,' " The Bachelorette alum said.

"I felt robbed of that before and taken advantage of that before. And used for that," she added of the on-air proposal. "And not knowing how precious that is to me."

February 1, 2023: Clare Crawley and Ryan Dawkins get married

During an intimate ceremony in Sacramento, California, Crawley and Dawkins wed.

"If I had to do this day over every single day for the rest of my life … I wouldn't change a thing!" Crawley told PEOPLE. "Happiest day of my life hands down!"

February 4, 2023: Dale Moss wishes Clare Crawley "nothing but the best"

Moss is happy that Crawley has found love with Dawkins.

"Everyone deserves to find love, love is a beautiful thing," he told PEOPLE. "If she's found love and they're happy, you know, how can you not be happy for her?"

The Bachelorette alum added: "So, I wish her nothing but the best. That's the goal, right?"