Clare Crawley and Ryan Dawkins' Relationship Timeline

When one rose wilts, another one starts blooming? Clare Crawley revealed that she first connected with now-boyfriend Ryan Dawkins the same month her engagement to Dale Moss officially ended.

“This picture was taken exactly one year ago,” the former Bachelorette wrote on September 25, 2022, via Instagram. “He asked me to dinner. I didn’t have an appetite. (Stressed & depressed) But I said yes to tea and a walk. Ended up laughing and smiling more than I did the entire last year combined.”

Crawley had an unconventional journey as the season 16 star of the ABC series, ending her stint after two weeks of filming to get engaged to Moss. While the pair were still going strong when their proposal aired in November 2020, they split for the first time in January 2021. They were back together by that February but still had problems to try to work through.

“They’re still working on some issues they have to overcome but it’s not like they make it known,” a source told Us Weekly in July 2021. “They’re more private when it comes to their issues. The good thing is that they’re happy together and enjoying this time as an engaged couple. They love each other very much and care for each other.”

By September 2021, things took another turn, and they broke up again as Crawley revealed that her mother, who has dementia and Alzheimer’s, had been placed in hospice care.

“Clare has seen everything by now for what is needed for her to have closure and not look back,” a source told Us at the time. “This past week has proven to her that he’s not someone who full-heartedly cares about her. He’s putting on an act for the public because he’s all about himself and his public image.”

A rep for Moss later fired back at the suggestion that he wasn’t supportive, claiming he traveled to support Crawley in October 2021.

“Dale and Clare broke up in mid-September when Clare was in New York City spending time with him,” his rep said at the time. “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. Dale flew to Sacramento last Tuesday morning to be with Clare, her mother and their family. [The following day], Dale flew to Los Angeles for a work obligation and had every intention to travel back to Sacramento to be with her, but his number was blocked, which made it impossible to communicate with Clare. It is unfortunate that the next time Dale heard anything from Clare, it was on social media.”

Moss, for his part, has since been linked to interior designer Galey Alix. While Crawley quietly began seeing Dawkins in late 2021, she didn’t go public with their relationship until September 2022.

“He’s mature, career-driven and a good father,” an insider told Us at the time. “He isn’t in it for fame, which is what makes him different from her past relationships.”

One month after going public, Dawkins proposed to Crawley in Las Vegas.

Scroll through for Crawley and Dawkins’ timeline:


September 2021
The pair started spending time together the same month that Crawley and Moss officially called it quits.  Courtesy of Clare Crawley/Instagram
Spring 2022
After spending time as friends in fall 2021, the twosome — quietly — took things to the next level. “She wanted to keep it private until she was ready to debut him as her new boyfriend. Close friends and family have known about it for a few months now, but it was her secret to tell,” a source told Us, noting that they “built a real solid foundation” before going public. Courtesy of Clare Crawley/Instagram
September 2022
Crawley shut down speculation that she got lip fillers, calling her swollen lips her “battle wounds” via Instagram. “Also, no I didn’t get my lips done, it’s the consequence of having sensitive skin + a hot man with a beard,” she quipped at the time. Image Press Agency/NurPhoto/Shutterstock; Inset Courtesy of Clare Crawley/Instagram
October 2022
After a source confirmed to Us that Dawkins popped the question, he gushed about his new fiancée. "Everything in my world has changed since I met her, she’s the love of my life and I wish the world knew the Clare that I know," he told Us. "She is one of the strongest women I know and is truly a light. I love our life and [am] beyond excited about our future." Courtesy of Clare Crawley/Instagram
October 2022
“I’m not getting any younger, but I don’t know. We haven’t really talked about it. Obviously, I’m thinking 2023,” Crawley told Us of wedding planning. “I wasn’t even in a rush to get engaged. I thought as long as I found my person, I’m happy.” She went on to gush: “He is different and more amazing than anything I’ve ever had. He brings so much calmness to me and so much security and is always reassuring and loving and just very consistent with how he loves me and doesn’t make me question it or doubt it for a second. And loving him is just easy.” DIRECTV

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