Clare Crawley & Dale Moss' Relationship Timeline Stresses Me Out

After several delays due to the ongoing coronavirus pandemic, Season 16 of The Bachelorette began filming in July 2020. The hairstylist was instantly wowed by the model, and awarded him the first impression rose. Less than two weeks later, fans were shocked to hear a rumor that Crawley was reportedly already in love with one of her contestants. As a source for Life & Style claimed on July 30, Crawley "told producers she no longer wanted to participate in the show" because she had "already fallen in love" with Moss.

A mere handful of weeks after laying eyes on each other, Moss proposed to Crawley at the La Quinta Resort & Spa, where The Bachelorette was filming. He popped the question with a 4.5-carat radiant-cut sparkler designed by (who else?) Neil Lane. Talk about bling.

After months of anticipation and rumors, The Bachelorette Season 16 finally premiered on Oct. 13. The chemistry between Crawley and Moss was undeniable from the moment he stepped out of the limo, and exactly no one was surprised when Moss popped the question during the Nov. 5 episode. Soon after the episode dropped, the two took to IG to finally share the exciting news. Then, just four days after the proposal aired, Moss posted a pic of himself with Crawley and his sister, making it clear he and his fiancée were still going strong.

"Everything since the show has been reaffirming of why I chose Dale," Crawley told People that same month. "He's even better off camera, in person, one on one at home. Dale is the yin to my yang. And this is the happiest I've ever been." Moss confirmed he felt the same way when he said, "For me personally, there is no explanation needed. I've never been afraid of commitment. And when I met Clare, I knew I was all in. She lights a fire in me that I was missing for so long."

Throughout November and December, Crawley and Moss continued to post loved-up pics together on Instagram. Some people even suspected the couple was already married after Crawley referred to Moss as her "husband" in a Dec. 10 Instagram Story, but Crawley later denied those rumors, claiming it was just a "slip of the tongue." Later on in the month, the couple rang in 2021 together.

Crawley and Moss seemingly started off the new year as strong as ever. During a Jan. 13 episode of Raising the Bar With Alli and Adrian, Moss even revealed he only agreed to appear on The Bachelorette after Crawley was announced as the lead. "Now, I could have never planned what happened because I was nominated," he said. "I never actually signed up. And I turned it down over and over and over again. And I actually finally committed to it four days before everyone was supposed to leave for the show. And the only reason I committed to it was because Clare was announced as Bachelorette at that time."

But fans noticed Moss was posting Instagrams from New York City, while Crawley appeared to be in Northern California. On Jan. 19, E! News reported the two were "taking time apart" after "fighting a lot."

"They are mainly in disagreement over lifestyle preferences," a source claimed. "Dale wants to be in a lively city and focus on his career, and Clare is rooted in Sacramento to help care for her mom. It's been very tense recently between them." The source added that the model cares deeply for his fiancée but "feels like he's rushing into something he's unsure about."

"They are both still getting to know each other and figuring it all out," E!’s source claimed. "They've decided to take some time apart for now... They are still figuring out the logistics of their relationship and if they will stay together."

On Jan. 19, another source claimed to Us Weekly, “Dale and Clare are technically still together but there are serious issues they are working through... They’re in communication but on a break.”

Moss confirmed his and Crawley's breakup on Jan. 19, putting an end to the speculation once and for all. "I wanted share [sic] with you all that Clare and I have decided to go our separate ways. We appreciate the love and support we've received from so many people, but this is the healthiest decision for both of us at this time," he wrote on Instagram Stories. "We strongly believe in leading with love and always remaining true to oneself - something our families have taught and instilled in us throughout our lives. We only hope the best things for one another."

Crawley and Moss reconciled in Feb. 2021. The two were seen holding hands and dining together in Florida.

“They were just hanging out, having a couple drinks,” a witness claimed to Us Weekly after spotting the couple at Nokomo’s Sunset Hut. “It was just the two of them. They were laying low and people kind of left them alone.”

Not long after they were seen sipping cocktails, a source gave E! the rundown on their breakup and apparent reunion.

“Dale had regret[s] over everything that happened between him and Clare and has been reaching out to her recently,” the source claimed. “She finally caved and decided to answer his calls and talk it out with him."

At this stage, the two weren’t an official item, but they were reportedly looking toward a shared future.

“Clare and Dale are not officially back together but are working on their relationship,” the source continued. “There's a lot of resentment but Clare can't ignore her feelings towards him. Clare has forgiven Dale for his actions and the messy split, and wants to move forward. She has expressed she's still in love with him and wants to make it work."

All but confirming their reunion, Crawley and Moss were seen kissing (through their masks!) in New York City on March 16, 2021 before dining together at Peak Restaurant.

“They were spotted holding hands during their dinner,” a witness told Us Weekly. “It was definitely a romantic night for the both of them.”

The next week, they celebrated Crawley’s 40th birthday together in Napa Valley, where they both posted Instagram Stories on March 21.

Shortly after their trip to Napa, Moss shared a mirror selfie of himself with Crawley — both sporting masks — on April 7, 2021.

A month and a half later, on May 28, he shared an adorable picture of them together on his feed.

“This makes me happy,” he wrote.

Following many ups, downs, and rumors, Crawley and Moss were reportedly engaged (again!) in July 2021.

“They’re engaged but still are working on building a solid relationship,” a source shared with Us Weekly. “They’ve discussed future plans but aren’t necessarily wedding planning. They aren’t rushing to tie the knot.”

Despite the source’s suggestion that Crawley and Moss were in no rush to walk down the aisle, Bachelor Nation started to wonder whether the pair had secretly gotten married (especially after Moss was spotted wearing a wedding band in Crawley’s Instagram story that August).

Curiouser and curiouser.

Here's hoping Crawley and Moss both have bright futures ahead of them, even though their plans no longer include each other.