Clare Crawley’s Dating History: From Bachelor Nation Stars 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.”

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:

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