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

Credit: ABC/Paula Lobo

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

Clare Crawley has a history with several members of Bachelor Nation! The hairstylist, who has been featured on The Bachelor, Bachelor in Paradise and Bachelor Winter Games, was named the season 16 Bachelorette in March 2020. “I cannot believe it. I mean, six years later,” Clare said on Good Morning America at the time. “What is happening?” The reality personality made history as the oldest Bachelorette lead in the franchise. She was 39 years old when she filmed her season. “I feel like a lot of people put [age] out there as this negative thing, but for me, it just is more years under my belt, more learning and knowing what I want, what I don’t want and what I won’t settle for,” Clare said on GMA in March 2020. “I’m wondering if they’re ready for me, for my age. I feel that would be more of an issue than me with them, because I feel so much younger at heart than my actual age. I’m proud of my age, but I just feel younger. That, to me, is what’s important.” [jwplayer tgvwWT2o-zhNYySv2] At the time, Clare added that she knew exactly what she wanted in a husband. “The most important thing is, I want a man who will take off his armor,” the California native explained. “I want a man who’s strong, who’s willing to take off the body armor, open himself up, and be vulnerable. I think that’s some serious strength right there.” During her historic season, she connected with Dale Moss on night one and less than two weeks later, the pair got engaged. Their romance didn't last, however. She has since found love with Ryan Dawkins. The twosome became Instagram official in September 2022 after keeping their romance under wraps for some time. Scroll through to revisit the men who caught Clare’s eye over the years:

Credit: ABC/Paula Lobo

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

Clare Crawley has a history with several members of Bachelor Nation! The hairstylist, who has been featured on The Bachelor, Bachelor in Paradise and Bachelor Winter Games, was named the season 16 Bachelorette in March 2020. “I cannot believe it. I mean, six years later,” Clare said on Good Morning America at the time. “What is happening?” The reality personality made history as the oldest Bachelorette lead in the franchise. She was 39 years old when she filmed her season. “I feel like a lot of people put [age] out there as this negative thing, but for me, it just is more years under my belt, more learning and knowing what I want, what I don’t want and what I won’t settle for,” Clare said on GMA in March 2020. “I’m wondering if they’re ready for me, for my age. I feel that would be more of an issue than me with them, because I feel so much younger at heart than my actual age. I’m proud of my age, but I just feel younger. That, to me, is what’s important.” [jwplayer tgvwWT2o-zhNYySv2] At the time, Clare added that she knew exactly what she wanted in a husband. “The most important thing is, I want a man who will take off his armor,” the California native explained. “I want a man who’s strong, who’s willing to take off the body armor, open himself up, and be vulnerable. I think that’s some serious strength right there.” During her historic season, she connected with Dale Moss on night one and less than two weeks later, the pair got engaged. Their romance didn't last, however. She has since found love with Ryan Dawkins. The twosome became Instagram official in September 2022 after keeping their romance under wraps for some time. Scroll through to revisit the men who caught Clare’s eye over the years:

Credit: ABC/Rick Rowell

Juan Pablo Galavis

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

“I thought I knew what kind of man you are,” Clare 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.”

Credit: ABC/Francisco Roman

Robert Graham

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

Credit: Rob Latour/Invision/AP/Shutterstock; ABC/Paul Hebert

Zack Kalter

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

Credit: ABC/Rick Rowell

Mikey Tenerelli

During Bachelor in Paradise season 2, Clare went out with another one of Des’ men: Mikey. 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”

Credit: ABC/Rick Rowell

Jared Haibon

Clare found herself wrapped up in a love triangle with Jared and (his now-wife) Ashley Iaconetti during season 2 of BiP. While their drama ended with Clare crying to a raccoon in a memorable edited moment, Ashley supported Clare 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,” Ashley 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.”

Credit: ABC/Paul Hebert

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 Clare 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."

Benoit supported Clare when the news broke in 2020. “Congratulations to this gem!! She will be an amazing Bachelorette,” he wrote via Instagram. “She is smart, fun, strong, knows what she wants and most importantly, she will call out the guys messing around!! Hell yeah!! Good Luck on your journey to find love @clarecrawley !! You will be the best 🙌🏼 #thebestbacheloretteever.”

Credit: YouTube (2)

Christian Rauch

Prior to getting engaged to Benoit, Clare was wrapped up in a love triangle with him and Christian.

Credit: ABC

Dale Moss

Less than two weeks into filming The Bachelorette, Clare got engaged to contestant Dale 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.”

Credit: ABC (2)

Blake Monar

Clare 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 Clare’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 Ryan, 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 Clare and Ryan are 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.