Clare and Dale got engaged on The Bachelorette's sixteenth season in 2020 and just celebrated their one-year anniversary in late July, when the pair gushed about their love for one another on social media.
The last Instagram post of Clare and Dale together dates back to September 10, when Clare shared a slideshow of photos from the U.S. Open tennis tournament, one of which featured Dale by her side along with fellow The Bachelorette couple Katie Thurston and Blake Moynes.
Both Clare and Dale uploaded the same picture of the foursome on their respective Instagram accounts.
Going back a little further, Clare also posted a picture of Dale and herself ordering from a food truck on August 29.
"Just us doing what we do best," Clare wrote at the time, after which Dale commented with five red-heart emojis.
Earlier this summer, Clare and Dale's relationship seemed stronger than ever. They had even been spotted wearing matching rings, which prompted speculation they might've had a secret wedding. (A source subsequently confirmed to Us Weekly that wasn't the case).
"They're engaged but still are working on building a solid relationship. They've discussed future plans but aren't necessarily wedding planning. They aren't rushing to tie the knot," the source said.
The source continued, "They're still working on some issues they have to overcome... They're more private when it comes to their issues."
"The good thing is that they're happy together and enjoying this time as an engaged couple. They love each other very much and care for each other."
Dale reportedly recently moved into a new place in New York City and Clare has been holding down her fort in Sacramento, CA, where she takes care of her mother suffering from Alzheimer's.
Dale and Clare already briefly split in January 2021 but began going on dates and spending time together again in February.
Dale appeared to confirm he got back together with Clare on April 7 when he posted a mirror selfie of the couple drinking coffee together on Instagram Stories.
The couple took things slowly and made sure they were on the same page about the future before getting back together, People reported, since they had allegedly disagreed on a post-engagement timeline for getting married and having children.
Clare's journey on The Bachelorette's sixteenth season in 2020 ended prematurely after about two weeks. Producers planned a steamy overnight date for the couple and then Dale proposed marriage seemingly the next day.
But on January 19, Dale announced he and Clare had decided to split and arrived at "the healthiest decision" for the "both" of them.
Clare then revealed two days later she had actually been blindsided by Dale's public statement.
Clare wrote on Instagram, "I was made aware of a 'mutual' statement at the same time you all were, so I've needed some time to really digest this."
Clare admitted she was "crushed" by the breakup given her intentions to settle down with Dale and start a family had "always been very clear."
The Season 16 The Bachelorette star added that she had been "genuinely invested with all of [her] heart" into Dale and their relationship, although it "was not perfect."
Multiple sources had described Dale as a "fame-seeker" in the wake of his split from Clare, according to E! News.
"[Dale] doesn't want to give up the party life. He loves the NYC scene," a source told E! News earlier this year. "His partying would be a problem in their relationship and would cause many fights."
Reports also swirled Dale had cheated on Clare, which he firmly denied in the press. Dale insisted on his Instagram Stories in late January that he loves and respects Clare and "wanted nothing more" than to make their relationship work.
"I put my heart and soul into it each and every day. And I wanted nothing more than to build a healthy relationship," Dale insisted, later adding that he was "hurting" from the breakup.