Clare Crawley’s Dating History Before ‘Bachelorette’: Her Epic Juan Pablo Breakup & More

Clare Crawley’s looking for her soulmate in the new season of ‘The Bachelorette.’ Clare is no stranger to Bachelor Nation and has had many whirlwind romances over the years.

Clare Crawley, 39, is starting a new chapter in her journey to find love on The Bachelorette. Clare is hoping to find the man she will spend the rest of her life with amongst the dashing suitors of season 16. Clare’s journey to this point hasn’t been an easy one, but it’s always been interesting.

Clare became a fan favorite from the moment she appeared on The Bachelor season 18. No matter what, Clare has been determined to find love. She’s never given up, and we love her for that. Take a look back at her dating history before The Bachelorette season 16 premiere.

Clare Crawley Juan Pablo Galavis
Clare Crawley fell for Juan Pablo Galavis on ‘The Bachelor.’ (ABC)

Clare first entered Bachelor Nation as a contestant vying for Juan Pablo Galavis‘ heart on The Bachelor season 18. Clare fell for Juan Pablo and ended up being in the final two. When Juan Pablo broke things off with Clare to be with Nikki Ferrell, she told him off in one of the most epic speeches in Bachelor Nation history. “I lost respect for you because I’ll tell you what… I thought I knew what kinda man you were. What you just made me go through? I would never want my children having a father like you,” she told Juan Pablo.

After her breakup with Juan Pablo, Clare spent two seasons on Bachelor in Paradise hoping to find love. She has a brief fling with Zack Kalter from Desiree Hartsock’s season, but she ultimately left BiP both times without love.

In 2017, Clare revealed on the Reality Steve podcast that she had actually dated other people from Bachelor Nation but didn’t name names. “I really don’t put my dating life at all on my social media,” she said when asked if she had dated other Bachelor alums. “The answer is yes. Like I said, with people either in the franchise…or in some way related to the franchise. Yeah, I have.”

Benoit Clare Crawley
Benoit Beausejour-Savard proposed to Clare Crawley. (ABC)

Clare returned to Bachelor Nation to find love on Bachelor Winter Games in 2018. During her time on the show, she became interested in both Benoit Beausejour-Savard, 33, and Christian Rauch. After a hot tub misunderstanding, Clare and Christian ultimately went their separate ways. From the very beginning, Benoit only had eyes for Clare. When he began to realize that Clare didn’t feel the same way about him at the time, he left the show. Clare and Benoit reconnected after filming had ended, and he proposed to her on After the Final Rose. Just two months later, they called off their engagement. However, they remain friends!

Clare Crawley
Clare Crawley is the new Bachelorette of season 16. (ABC)

Clare was announced as the new Bachelorette for season 16 in March 2020 on Good Morning America. She will be the oldest Bachelorette in the show’s history at 39 years old. She’s ready to open her heart once again!