Clare Crawley’s Dating History: A Guide to Her Bachelor Nation Romances and Beyond

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Clare Crawley's Dating History: A Guide to Her Bachelor Nation Romances and Beyond

Clare Crawley competed on The Bachelor and several spinoffs before becoming the season 16 lead of The Bachelorette in March 2020. Her love story, however, didn’t end there. During her historic season — she was the oldest Bachelorette lead ever, filming at age 39— Crawley connected with Dale Moss on night one and less than two weeks later, the pair got engaged. Their romance, unfortunately, didn’t last. After a brief split in January 2021, the exes called it quits for good in September 2021 — but Crawley didn’t let a failed engagement get her down. She moved on with Ryan Dawkins in fall 2021. Crawley and Dawkins went Instagram official in September 2022 after initially keeping their romance under wraps. The couple tied the knot the following year. In July 2023, Crawley announced that she and Dawkins are expecting a baby via surrogate. Scroll down to revisit the men who caught Crawley’s eye over the years — and to find out why some of them didn’t last:

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Juan Pablo Galavis

Crawley first competed for Galavis' heart on season 18 of The Bachelor. During the finale, the former soccer player dumped the California native for Nikki Ferrell — but Crawley was more "shocked" that the lead "chose to tell [her] something that no woman wants to hear" behind-the-scenes. (It was rumored that Galavis told Crawley that he didn't love her, but loved "f--king her.")

“I thought I knew what kind of man you are,” Crawley declared on the March 2014 finale. “I lost respect for you. Because, I’ll tell you what. I thought I knew what kind of man you were. What you made me go through, I would never want my children having a father like you.”

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Robert Graham

Crawley's first date on Bachelor in Paradise season 1, which aired during the summer of 2014, was with Graham, who appeared on Desiree Hartsock’s season of The Bachelorette 2013. While he gave Crawley a rose during week 1, they didn’t last.

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Zack Kalter

Crawley's most prominent relationship on BiP season 1 was with Graham's fellow Bachelorette season 9 contestant Kalter. While the twosome dated for several episodes, their romance came to an end after AshLee Frazier told Kalter that Crawley was a “cuckoo.” Amid the drama, Crawley quit the show.

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Mikey Tenerelli

During Bachelor in Paradise season 2, Crawley went out with another one of Hartsock's men: Tenerelli. While their romance only lasted one tantric yoga date, he sent her love after the Bachelorette announcement in March 2020.

“Congrats to our next @bacheloretteabc,” he wrote. “Let’s hope your experience this time around is better than this date! 😝#bip #2016”

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Jared Haibon

Crawley found herself wrapped up in a love triangle with Haibon and (his now-wife) Ashley Iaconetti during season 2 of BiP. While their drama ended with Crawley crying to a raccoon in a memorable edited moment, Iaconetti supported Crawley as the Bachelorette before ABC even made the announcement.

“Clare and I had some beef back when she went on a date with Jared on BiP 2 but I became really good friends with her on Bachelor Winter Games,” Iaconetti told Us at the time. “She is such a self-assured woman. She is not going to deal with anything that is below her. She will call you out, she is very smart, she is beautiful, she is very nurturing, warm, and I feel like she has so many great qualities for a Bachelorette. She would be entertaining, real, raw. I can keep going on and on but I do think she would be a fantastic Bachelorette and I feel like there were certain times where she was in the running for it and then there was always somebody who kind of beat her out. So if we’re trying to get older in the franchise, let’s go with somebody in their 30s.”

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Benoit Beauséjour-Savard

Clare got engaged to the Bachelorette Canada star after meeting on season 1 of Bachelor Winter Games, which aired in 2018. While Crawley went home alone when filming ended, the pair rekindled their romance and he proposed during a live February episode. They split that April.

"It's with a heavy heart that we have mutually decided to end our relationship," the twosome said in a joint statement at the time. "We think the world of each other, and we were both hoping we could make this work. I'm sorry that this may not be what you want to hear, but it's our truth. Just know there are no negative feelings here, we are simply two people who believed in love, and were open enough to give it a chance."

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Christian Rauch

Prior to getting engaged to Beauséjour-Savard, Crawley was wrapped up in a love triangle with him and Rauch.

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Dale Moss

Less than two weeks into filming The Bachelorette, Crawley got engaged to contestant Moss in an episode that aired in November 2020. Us revealed in January 2021 that the two were having "serious issues" and later confirmed they had split. Moss later confirmed via social media that they called off their engagement.

One month later, however, the twosome were spotted holding hands and kissing in Florida. Us subsequently broke the news that they were giving their romance another shot.

That September, however, the pair called it quits again and for good.

“If my biggest regret is trusting the process, trusting a man’s words and who he showed me he was, I don’t think that that’s a regret,” she said on “Whine Down” after the split. “I trusted somebody, I believed somebody that they were who that they said they were [and] that they would hold up to the promises that they make when they get down on one knee.”

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Blake Monar

Crawley was linked to the season 16 contestant in early 2022, but a source later told Us that they “were never officially dating.” The insider added: “They hung out a few times and enjoyed each other’s company at the time.”

Credit: Image Press Agency/NurPhoto/Shutterstock; Inset Courtesy of Clare Crawley/Instagram

Ryan Dawkins

Us exclusively confirmed the identity of Crawley's new man in September 2022 after she teased via Instagram that she found her “perfect match.”

“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 about Dawkins, noting they started out as friends. “He’s mature, career-driven and a good father. He isn’t in it for fame, which is what makes him different from her past relationships.”

Less than a month later, Us confirmed that Crawley and Dawkins were engaged, with a source revealing that the businessman proposed in October 2022 while attending RiSE in Las Vegas. They tied the knot in February 2023 in Sacramento. The couple announced in July 2023 that they are expecting their first baby via surrogate, due in 2024.