Bachelorette Clare Crawley and Dale Moss’ Relationship Timeline: The Way They Were

Credit: ABC/Craig Sjodin

Bachelorette Clare Crawley and Dale Moss' Relationship Timeline: The Way They Were

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." [jwplayer mu4jVlsy-zhNYySv2] 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: [podcast_block]

Credit: ABC/Craig Sjodin

First Meeting

Upon meeting Moss on The Bachelorette — which filmed in the summer of 2020 — Crawley was taken back by how attracted to him she was. "I definitely feel like I just met my husband," she said. "Every other guy, I felt confident with, but with Dale, everything else went dark around me. I felt everything that I haven’t felt ever. … I felt it. I just know."

Credit: ABC/Craig Sjodin

First Impression Rose

After her reaction to meeting him was so strong, it was no surprise that he also received the first impression rose at the end of night one.

Credit: ABC/Craig Sjodin

Sharing a Kiss

Their first kiss was steamy, as she pulled him in on night one. "Even though it was in one night, we connected in so many different levels," Moss later said. "I would love to sit and talk with her for a couple more hours."

Credit: ABC/Craig Sjodin

Admitting Her Feelings

When no one got up and asked to steal her away during a group date, Crawley was offended. Moss then stepped in, and she admitted to him, "I totally have feelings for you." He responded, "I totally feel the same way."

Credit: ABC

A Shoulder to Cry On

After Yosef Aborady upset Crawley by saying he's embarrassed of her — and she sent him packing — Moss came to her rescue, embracing her in a hug and telling her how wrong Aborday was. "You don't deserve that," he said on the October 27, 2020, episode. "He's lying, everyone's lying if they say they don't want to spend time with you."

In turn, Clare said in her interview, "All I've ever wanted is a man like Dale, who will come over and protect me and make sure that I'm OK and not have to go through it alone."

Credit: ABC/Craig Sjodin

Heating Up

During the October 27, 2020, episode, Moss grabbed Crawley first to chat for "five minutes" after the group date. Instead, the pair spent nearly an hour in her room, making out in her bed. She later told producers she wanted to hurry through the rest of the dates.

Credit: ABC/Craig Sjodin

The F-Word

After many of the men roasted Moss very hard during a group date during the October 27, 2020, episode, Crawley was not happy. When talking to a producer she said that the group "dished on my fiancé so hard."

Credit: ABC/Craig Sjodin

...And the L Word

"Dale is everything that I'm looking for, everything that I want and can't put words with. Things you can't explain," Crawley later stated during one of her interviews. "I can't believe, it's not even the second rose ceremony yet, and I'm so falling in love with Dale."

Credit: ABC/Craig Sjodin

Engaged

During the November 5, 2020, episode, Crawley broke up with the remaining men and told Moss she loved him. He echoed her sentiments and the pair got engaged and left the show.

Credit: Courtesy of Dale Moss/Instagram

Life in the Real World

Crawley and Moss documented their trip to see his sisters in South Dakota in November 2020. Later that month, the pair, who were house hunting in Sacramento, enjoyed Thanksgiving at Moss' family home in La Jolla, California.

Credit: Courtesy of Dale Moss/Instagram

Did Someone Say Wedding Bells?

In December 2020, Crawley had fans convinced that she and Moss had taken the next big step in their relationship after calling him her "husband" in an Instagram Story. Despite speculation, the reality star quickly cleared the air. "Slip of the tongue!" she joked at the time. "We aren't married!"

Credit: Craig Sjodin/ABC; Gregory Pace/Shutterstock

Ups and Downs

Two months after their engagement played out on national television, a source exclusively told Us that the Bachelor Nation pair had hit a snag in their relationship. "Dale and Clare are still together but there are serious issues they are working through," the insider said in January 2021.

Credit: ABC/Craig Sjodin

Dunzo

Moss confirmed in January 2021 that he and Crawley ended their engagement. 

“I wanted [to] share with you all that Clare and I have decided to go our separate ways,” he wrote via Instagram Stories. “We appreciate the love and support we’ve received form so many people, but this is the healthiest decision for both of us at this time. 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.”

Credit: Courtesy of Dale Moss/Instagram

Round 2?

The former couple were spotted together in February 2021 drinking Moscow mules at Nokomo’s Sunset Hut in Nokomis, Florida. They were also photographed holding hands.

Credit: Craig Sjodin/ABC

Playing Coy

As their reunion made headlines — and after the duo shared matching Instagram Stories from the same Florida restaurant — Moss hinted that he was feeling positive in the wake of his and Crawley's split.

"A lot to smile about lately. #GodIsGood 🙏🏽," he wrote via Instagram in February 2021. One day earlier, an eyewitness told Us that he and Crawley kept things casual while hanging out at Nokomo's Sunset Hut in Nokomis, Florida.

"It wasn't anything out of the ordinary. ... They looked more like they were friends," the onlooker explained. "They were smiling and enjoying each other's company, but it wasn't like they were all over each other."

Credit: ABC/Craig Sjodin

Not Giving Up

During their February 2021 reunion in Florida, a source told Us that the former Bachelorette’s “love for Dale didn’t just disappear overnight. She still has strong feelings for him. Once she falls in love, she falls hard.”

Another source told Us that the twosome are “figuring things out and enjoying spending time together.”

Credit: ABC/Craig Sjodin; Evan Agostini/Invision/AP/Shutterstock

Sealed With a Kiss

Crawley and Moss solidified their reconciliation by packing on the PDA in New York City ahead of her 40th birthday in March 2021.

Credit: Courtesy of Dale Moss/Instagram

Dynamic Duo

After weeks of speculation, Moss confirmed that he had rekindled his relationship with the hairstylist as they cozied up for a playful bathroom mirror pic. "Selfie skills on 💯," he captioned an April 2021 Instagram Story.

Credit: Courtesy of Clare Crawley/Instagram

Are They Engaged?

Crawley showed off her massive diamond ring in an April 2021 Instagram Story, instantly causing fans to wonder whether she and Moss were engaged once again.

Credit: Courtesy Dale Moss/Instagram

Instagram Official

Moss shared his first grid photo of Crawley in April 2021 via Instagram since their reunion. "This makes me happy," he captioned the picture, which showed the couple wearing matching necklaces. The Sacramento native's engagement ring was also visible on her left hand.

Credit: Courtesy Clare Crawley/Instagram

Goofing Off

"Rooftop fedora party of 2!!" the former Bachelorette star captioned a photo via Instagram of the pair showing off their matching hats during a night out in June 2021.

Credit: Courtesy Dale Moss/Instagram

Spring Fling

Moss shared a photo of him and Crawley smiling in the sunshine on a bench via Instagram. "Life has a funny way of working things out," he captioned the happy snap in June 2021. 

Credit: Courtesy Clare Crawley/Instagram

In Sickness and In Health

In July 2021, the California native revealed that she was getting her breast implants removed after months of health struggles. She detailed her ups and downs in an Instagram video, sharing that doctors found “fluid sacks” behind the implants that may have caused her white blood cell count to go up recently. “My body is fighting [my implants],” she said. “My body can’t heal. My body is in fight mode constantly.”

The former reality star then shared a sweet comment her boyfriend made, telling her fans, “I was talking to Dale the other day and he said, ‘Your boobs are not what make you beautiful.’ And it’s the truth. For so long I believed that’s what it would take. To me, this is the ultimate love story — loving body enough to know this is not what makes me beautiful. My health and happiness is what matters.”

Dale then applauded Clare for sharing her story, commenting on the post, “So proud of you for sharing this love. I know this wasn’t easy but will help so many other women going through what you’ve been experiencing. I love you & with you every step of the way❤️.”

Credit: Courtesy Dale Moss/Instagram

USA!

“One for the books! Sending y’all love this 4th of July Holiday!” Moss captioned a photo with his love on Independence Day in July 2021. The couple, who were color-coordinated, celebrated the holiday in New York City. 

Crawley, for her part, reflected on how far she has come since July 2020, when she left to be the Bachelorette. “Happy 4th of July🎆!!! This exact day/time last year I was packing my car and heading out solo to Palm Springs … What a difference a year makes!” she captioned a similar photo.

Credit: Courtesy of Dale Moss/Instagram

1 Year Together

In July 2021, Crawley posted a video montage, beginning with the pair's first meeting. "Happy ONE YEAR Anniversary love," she captioned the post. Moss commented, "Love you with all my heart. Before we even met I knew god was working but never could have imagined what he had in store for us and there’s so much more ahead. My heart is with you always."

Moss posted a tribute of his own to mark the milestone, sharing an Instagram photo of the duo kissing. "It’s the moments that nobody sees that make life and our love so special," he wrote. "The most beautiful thing is that those are the moments only we will carry forever. When we first met I knew god’s hand was at work but I could have never imagined the journey he had in store for us. Love you with all my heart @clarecrawley ❤️. Happy ONE YEAR Anniversary Love!"

Credit: Sara Jaye Weiss/Shutterstock; MediaPunch/Shutterstock

Last Public Appearance?

In early September 2021, Crawley and Moss spent time with Bachelorette season 17 couple Katie Thurston and Blake Moynes at the US Open. While discussing the outing, Moss told Us he gave the newly engaged advice.

“Share the happy moments and everything like that, but as you build, the No. 1 thing is just to have a certain level of privacy and support one another to the best of your abilities,” he said on September 22. “And, you know, it’s always great when you can spend as much time together as possible, especially because the distance is something that can be very difficult in those situations.”

Credit: Courtesy Clare Crawley/Instagram

Over Again

After Moss attended a wedding solo and celebrated his birthday without Crawley in September 2021, a source told Us that the twosome split again.

“They have different visions and wedding planning wasn’t happening which made Clare really upset,” the insider said. “She wants to be in Sacramento to be close to her family, especially her mom who isn’t well. Dale wants to remain in NY.”

Credit: Courtesy of Clare Crawley/Instagram

Putting on a Performance?

In December 2021, the trailer for Moss' acting debut dropped on YouTube, which prompted Crawley to respond. In the Love, Game, Match teaser, Dale plays a tennis coach who falls for a fellow high school teacher.

Shortly after the trailer made headlines, Crawley seemingly threw shade at her ex when she told her followers to “stop sending me all the acting reel clips … I had a front row seat to that since day one.”

Credit: ABC(2); Shutterstock

Bachelor Nation Reunion

After briefly being linked to comedian Jeff Dye in November 2021, Crawley had Bachelor Nation buzzing in January 2022 after she hung out with former Bachelorette suitor Blake Monar.

“Went for business, left with the most unexpected remarkable memories! Indy, you were truly beautiful and exactly what my soul needed,” she captioned a video montage of memories from her trip to Indiana.

The clip included footage of Crawley shopping and duckpin bowling with the former baseball player, who was eliminated during the second week of her Bachelorette season. The pair got cozy in a car and played with Monar’s nephew in the video.

Credit: Shutterstock; Instagram; ABC

Moving On?

Moss sparked a romance with model Florencia Galarza in January 2022, with a source exclusively telling Us at the time, “It’s very casual.” The duo were spotted out together in New York City earlier that month, but the insider noted, “They aren’t officially dating.”

Credit: Evan Agostini/Invision/AP/Shutterstock

Sending His Well Wishes

One month after Crawley announced her engagement to Ryan Dawkins, Moss broke his silence on the news. "I don't get too much into other people's relationships — I am in a very happy strong relationship right now. That's my focus," the former professional football player, referring to girlfriend Galey Alix, told Access Hollywood in November 2022. "But I will say we all deserve to find love and that's one of the best things in the world. Everyone is deserving of that."