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Bachelorette Clare Crawley and Dale Moss' Relationship Timeline

When you know, you know … or you hope you know? Season 16 of The Bachelorette was like no other. From the moment Clare Crawley met Dale Moss on night one of the ABC dating show, things were different.

It was breathtaking. It was one of those moments where you don’t know it until you experience it, what exactly that feeling is,” the hairstylist exclusively told Us Weekly ahead of the premiere in October 2020. “I still can’t put it into words what that feeling is though. It was when your body has that kind of, like, a goosebumpy reaction to things; it just takes your breath away.”

Us confirmed in August 2020 that the Bachelor in Paradise alum exited the show after finding love in less than two weeks. However, she stands by the fact that she and Moss did not talk ahead of her season. (Her cast was announced months before filming began as the coronavirus pandemic delayed production from March 2020 to July of that year.)

“There was never a moment where I was going to reach out or I wanted to reach out [to the contestants] because I knew that this was going to happen eventually where I was going to get the chance to meet these guys,” she told Us in October 2020. “I didn’t want to kind of prejudge anybody and shoot myself in the foot by having these conversations and putting that at risk. ‘Cause it’s like, you only really know when you meet them in person and it can actually be around their pheromones to see them in person to know, do we have that connection? So if I was to start something up with a guy beforehand, it would just be doing myself a disservice … I’d be putting it all on the line for that? I mean, that makes no sense to me.”

However, the journey for the duo wasn’t an easy one. After connecting on night one, she fell hard — and the other suitors were not happy.

“She doesn’t really care about anybody else or giving anyone else a fair shake, besides Dale,” contestant Kenny Braasch said to the other men during an October 2020 episode of the show. “If you want to go be with Dale, go be with him now and we’ll all go home. If you’ve already got a boyfriend, what am I doing here?”

Clare, for her part, knew that there were going to be critics who wondered how she could fall so quickly — but she wasn’t worried about them.

“My question would be to the people that are saying that — to the people that question it — what exactly is the formula for falling in love?” she asked during Us’ interview. “Is there one way to do it? Is there one example of this is how it’s done?”

In January 2021, Us confirmed that Crawley and Moss’ relationship hit a road bump. He later confirmed that they called it quits, but the split didn’t last long. Us broke the news in February 2021 that they were giving it another shot.

Us confirmed in September 2021, that the pair split for a second time less than one year after reconciling. “It was best for them to go their separate ways at this time,” an insider told Us at the time.

Scroll through the gallery below to see a timeline of Moss and Crawley’s relationship — from night one to now:

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