From ‘The Bachelorette’ to Now! A Timeline of Clare Crawley and Dale Moss’ Complicated Relationship

It was hard to keep up! Clare Crawley and Dale Mossrelationship timeline went from an instant spark on The Bachelorette to getting engaged just a few weeks into filming. However, it wasn’t long until the pair’s engagement hit a wall. “Clare and I have decided to go our separate ways,” Dale revealed on Instagram on January 19 amid mounting split speculation from fans. “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.”

The duo sparked reconciliation rumors, however, when they were spotted out for a stroll together in photos and videos obtained by Reality Steve in Venice, Florida. Neither of them lives in the Sunshine State, so it would seem the February 16 rendezvous was planned.

Prior to their relationship ending, Life & Style exclusively confirmed in July 2020 that the Sacramento native threatened to quit season 16 because she had “fallen in love” with the handsome contestant. Talks among production said the retired football player popped the question a few days later, and they got engaged. Of course, viewers finally got to see Dale get down on one knee during episode 4 in November.

That said, their connection started even before he stepped out of the limo. Filming for Clare’s season was delayed in March amid the coronavirus pandemic. Production picked back up four months later in July, but the hairstylist confessed to checking out her contestants via social media during an appearance on the “Bachelor Happy Hour” podcast with Rachel Lindsay and Becca Kufrin in June. 

“You can kind of tell people’s lifestyles like from Instagram Stories, and I see some that I’m like, ‘That’s not really my vibe,’ and others where I look at them and I’m like, ‘Oh, that’s hot. I can’t wait to meet that guy. I hope he’s on the season,'” she explained at the time.

Clare vetting out her contestants helped Dale stand out. “Dale, in a lot of his Stories, he would talk about his mom and he’d talk about his family. He was with his family a lot and that is something that deeply resonates with me,” the leading lady told Entertainment Tonight in October. “I just felt on any level, whether it be friendship, whether it be a romantic connection, I just felt like there would be that good connection with him. But you ultimately don’t know if it’s a romantic connection, because you’re just seeing him through social media.”

The former wide receiver was “definitely looking for a serious relationship” prior to season 16, an insider close to Dale previously told Life & Style. “He was very excited to go on the show. He felt it was a good opportunity for growth and to meet somebody … I think his intentions for going on the show are just to give it a try.”

Clare’s relaxed, California-vibe seemed to align with Dale’s sweet personality. “He’s definitely a lovable guy,” added the insider. “He’s open for anything and everything. He goes into things with an open heart and anything that comes [from] it, he’s cool with.”

Production brought in Tayshia Adams as the new Bachelorette, and Bachelor Nation happily watched the Bachelor in Paradise alum fall in love with contestant Zac Clark, to whom she got engaged during the finale.

Scroll through the gallery below to see Clare Crawley and Dale Moss’ complicated relationship timeline.