Clare Crawley has to be the most unconventional Bachelorette to ever be. But how fitting that she would be the Bachelorette during the year 2020, the most unconventional year most of us have ever seen.Â
Clare Crawley was the Bachelorette on the still currently airing Season 16 of The Bachelorette. However, this isn’t even close to her first time in the franchise. She is best known for being the runner-up on Juan Pablo’s season 18 of The Bachelor. She also appeared in both season one and two of Bachelor in Paradise as well as the Bachelor Winter Games back in 2018.Â
It wouldn’t be right to dive into this season without first talking about some of the men that Clare has dated in the past.
When Clare first stepped out of the limo on Season 18 of The Bachelor back in 2014 it was to meet Juan Pablo Galavis. Their relationship was full of ups and downs from the start. While they seemed to hit it off in the beginning when he offered her the first one-on-one date, the couple always seemed to run into problems. With multiple fights and hard conversations throughout the season, it’s baffling how Clare made it to the final rose ceremony. When Juan Pablo inevitably did not pick her she stormed out of the ceremony saying, “I thought I knew what kind of man you were. I lost respect for you. What you just made me go through? I would never want my children to have a father like you.” Classy as ever, Juan Pablo simply put his head down and said “I’m so glad I didn’t pick her!”
Shortly after she was on the first season of Bachelor in Paradise in 2014 where she dated Zack Kalter. The couple dated for only a couple short weeks before splitting and Clare leaving the show empty handed, yet again.
She returned to Bachelor in Paradise the following summer of 2015 where she made a connection with Jared Haibon. They dated for a couple of weeks before he decided that the eight-year age difference was an issue for him and the couple ultimately went their separate ways.Â
She then went on to the first-ever season of Bachelor Winter Games in 2018. At the end of the season, she ended up engaged to Benoit Beausejour-Savard, who is originally from Montreal and part of the Canadian Bachelor franchise. While their engagement never ended in marriage, the two have no animosity towards each other. When she was announced as The Bachelorette back in March of 2020, he took to Instagram to say “Congratulations to this gem!! She will be an amazing Bachelorette. She is smart, fun, strong, knows what she wants and most importantly, she will call out the guys messing around!! Hell yeah!” He has been publicly cheering her on throughout her season over Instagram since and when the news broke about her new engagement to Dale Moss he was quick to comment on her post “You deserve all the love and happiness!! Happy for you two.” He even adds in an interview with the famous Chris Harrison that they still keep in touch saying, “She has always been so nice to me, even after the breakup. We talked on a regular basis and still care a lot about each other.”Â
When Clare Crawley was announced as the Bachelorette back in March of 2020, it sent shock waves through the Bachelor community. In recent years, Bachelorettes, Bachelors, and their contestants seem to be getting younger and younger. The youngest Bachelorette to ever appear on the franchise was Hannah Brown, at the age of 24 back in 2019. However, they took a different turn this year naming Clare Crawley, the oldest Bachelorette to ever appear on the franchise at the age of 39. However, Clare Crawley seems proud to be the oldest Bachelorette making multiple references to the fact that she refuses to settle even with all of her past relationships and previous engagements on the show.Â
Despite being the oldest Bachelorette, Clare’s group of men are surprisingly young for her. They range from ages 26-40, but 12 of her men are under the age of 30! Bennett, one of the stars to come out of this season was the only contestant older than her at the age of 40.
The season was off to a very rocky start back in March when filming had to stop due to COVID-19. However, only a few months behind schedule, the show found a way to film during the pandemic by taking the mandatory precautions and creating a very large bubble. The entire cast and crew were required to quarantine and endure regular COVID testing in order to ensure safety for everyone. Unfortunately, travel for this season was also out of the question so the entire season was filmed at the La Quinta Resort in Palm Springs, California.Â
While she’s had her fair share of highs and lows on previous seasons, and a rough start to her own, nothing can compare to when Dale Moss stepped out of the limo on her season of The Bachelorette nearly four weeks ago.Â
The couple seems to have had a love at first sight moment when Dale walked out of the limo. They had a short conversation where Clare bashfully shook her head and said “nice to meet you, Dale!” Clare claims to have blacked-out, calling to producers after he had made his way inside asking… “what did I say?” While you could say Clare tried to keep her cool as long as possible, she started forgetting about the other men quickly and it became very apparent early on that she wasn’t interested in getting to know anyone but Dale. She even failed to give out a rose on the third group-date saying that she didn’t feel that she had made a connection with anyone.Â
At this point, the guys in the house knew what was up and had a lot of questions for Clare. Chris Harrison had to step in and intervene when he saw that Clare wasn’t playing along with the show and put a stop to her season. Clare came clean confessing that she was head over heels in love with Dale and that she was excited to tell him and find out if he was feeling the same way. Chris told her she had to break up with all of the men before she could continue her relationship with Dale any further. In an awkward conversation with the remaining men she breaks up with all of them only to end her speech with “I’m going to miss you guys.” Awkward.
Chris Harrison arranged for the couple to have a final overnight “fantasy suite” type date before telling Dale that it was time for him to propose. While this episode is a total nail biter, Dale does end up on one knee in the end and the couple is currently engaged.
While it’s uncertain if the couple will end up married or not, I wish them the best with their engagement and their future!
If you haven’t seen the season yet, it’s a must-see as Chris Harrison doesn’t lie when he tells you it’s the most dramatic season in Bachelorette history!