Clare Crawley's Dating History: A Guide to Her Bachelor Nation Romances
Clare Crawley is about to embark on relationships with 25 men on The Bachelorette, but she already 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, who will turn 39 while filming the ABC dating show, made history as the oldest Bachelorette lead in the franchise.
“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,” she said on GMA. “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.”
Clare added that she knows what she wants in a husband.
“The most important thing is, I want a man who will take off his armor,” she said. “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.”
Scroll through to revisit the men who caught Clare’s eye in the past:
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.”
ABC/Rick Rowell
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.
ABC/Francisco Roman
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.
Rob Latour/Invision/AP/Shutterstock; ABC/Paul Hebert
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”
ABC/Rick Rowell
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.”
ABC/Rick Rowell
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.”
ABC/Paul Hebert
Prior to getting engaged to Benoit, Clare was wrapped up in a love triangle with him and Christian.
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