![Clare Crawley and Dale Moss Relationship Timeline](https://www.lifeandstylemag.com/wp-content/uploads/2020/10/Clare-Crawley-Dale-Moss-Relationship-Timeline-Feature.jpg?crop=598px%2C73px%2C2042px%2C1157px&resize=940%2C529&quality=86&strip=all)
ABC/Craig Sjodin
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 Moss’ relationship 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.
The dynamic duo was plagued with cheating rumors following their shocking split — but in April 2021, Dale revealed on the “Hollywood Raw podcast with Dax Holt and Adam Glyn” that the speculation didn’t even factor into his reconciliation talks with Clare.
“That was never a conversation, even when we went through our split. It wasn’t even a thing. It was never even a topic of conversation,” he said on the show. “You really have to look past that and focus on one another. I mean, that sucked. When things are going at your character, and something you’re completely against, those are the hardest things to handle.”
Scroll through the gallery below to see Clare Crawley and Dale Moss’ complicated relationship timeline.
![Clare Crawley and Dale Moss Relationship Timeline Bachelorette to Now](https://www.lifeandstylemag.com/wp-content/uploads/2020/08/shutterstock_editorial_5826226bo.jpg?fit=800%2C1200&quality=86&strip=all)
Marion Curtis/Starpix/Shutterstock
![Clare Crawley and Dale Moss Before Bachelorette Relationship Timeline](https://www.lifeandstylemag.com/wp-content/uploads/2020/08/Clare-Crawley-and-Dale-Moss-Before-Bachelorette.jpg?fit=800%2C743&quality=86&strip=all)
Courtesy Clare Crawley/Instagram; Abel Fermin/Shutterstock
![Clare Crawley and Dale Moss Relationship Timeline Bachelorette to Now](https://www.lifeandstylemag.com/wp-content/uploads/2020/09/155774_017.jpg?fit=800%2C450&quality=86&strip=all)
ABC
![why did clare crawley quit the bachelorette](https://www.lifeandstylemag.com/wp-content/uploads/2020/08/why-did-clare-crawley-quit-the-bachelorette.jpg?fit=800%2C640&quality=86&strip=all)
ABC/Paul Hebert
![Bachelorette Clare Crawley Looks Serious on Bachelor Winter Games](https://www.lifeandstylemag.com/wp-content/uploads/2020/06/148313_5319.jpg?fit=800%2C533&quality=86&strip=all)
ABC/Lorenzo Bevilaqua
![Bachelorette Clare Crawley Net Worth Makes Money as Hairstylist](https://www.lifeandstylemag.com/wp-content/uploads/2020/07/clarecrawley_59289036_611190269382112_9024187228542656040_n.jpg?fit=800%2C945&quality=86&strip=all)
Courtesy Clare Crawley/Instagram
![Clare CrawleClare Crawley Kisses Dale Mossy Kisses Dale Moss](https://www.lifeandstylemag.com/wp-content/uploads/2020/09/Eg3MCG8XcAAyaaU-e1599063391533.jpg?fit=800%2C347&quality=86&strip=all)
ABC
![dale-moss-wants-to-be-a-father-5-years-after-clare-crawley-engagement](https://www.lifeandstylemag.com/wp-content/uploads/2020/09/dale-moss-wants-to-be-a-father-5-years-after-clare-crawley-engagement.png?fit=800%2C1413&quality=86&strip=all)
![Clare Crawley and Dale Moss on The Bachelorette](https://www.lifeandstylemag.com/wp-content/uploads/2020/10/155354_4442.jpg?fit=800%2C533&quality=86&strip=all)
ABC/Craig Sjodin
![Bachelorette Clare Crawley and Dale Moss' Cutest Photos So Far 4](https://www.lifeandstylemag.com/wp-content/uploads/2020/10/155354_1351-1.jpg?fit=800%2C641&quality=86&strip=all)
ABC/Craig Sjodin
![Clare Crawley and Fiance Dale Moss first Impression Rose Relationship Timeline](https://www.lifeandstylemag.com/wp-content/uploads/2020/08/shutterstock_editorial_5623352v-1.jpg?fit=800%2C1200&quality=86&strip=all)
Gregory Pace/Shutterstock
![Bachelorette Clare Crawley and Contestant Dale Moss Relationship Timeline](https://www.lifeandstylemag.com/wp-content/uploads/2020/10/155681_4022.jpg?fit=800%2C534&quality=86&strip=all)
ABC/Craig Sjodin
![Bachelorette Clare Crawley and Fiance Dale Moss Relationship Timeline](https://www.lifeandstylemag.com/wp-content/uploads/2020/10/155681_3572.jpg?fit=800%2C641&quality=86&strip=all)
ABC/Craig Sjodin
![Clare Crawley and Dale Moss Relationship Timeline](https://www.lifeandstylemag.com/wp-content/uploads/2020/10/Clare-Crawley-Dale-Moss-Relationship-Timeline-Engagement.jpg?fit=800%2C533&quality=86&strip=all)
ABC/Craig Sjodin
![when-dale-moss-knew-clare-crawley-was-the-one](https://www.lifeandstylemag.com/wp-content/uploads/2020/11/when-dale-knew-clare-was-the-one-e1604681044120.jpg?fit=800%2C1201&quality=86&strip=all)
ABC/Craig Sjodin
![Chris Harrison Reveals If He Thinks Clare and Dale Will Stay Together](https://www.lifeandstylemag.com/wp-content/uploads/2020/11/chris-exclusive-dale-clare.jpg?fit=800%2C641&quality=86&strip=all)
ABC/Craig Sjodin
![clare-crawley-dale-moss-house-hunting](https://www.lifeandstylemag.com/wp-content/uploads/2020/11/clare-crawley-dale-moss-house-hunting-ig.jpeg?fit=800%2C1420&quality=86&strip=all)
![Ever Bachelor Engagement Ring Ranked by Carat Size](https://www.lifeandstylemag.com/wp-content/uploads/2020/11/155744_1444.jpg?fit=800%2C641&quality=86&strip=all)
ABC/Craig Sjodin
![Clare Crawley and Dale Moss Relationship Timeline](https://www.lifeandstylemag.com/wp-content/uploads/2021/01/133491780_425988591887657_2133443144053388937_n.jpg?fit=800%2C892&quality=86&strip=all)
Courtesy Dale Moss/Instagram
![Clare Crawley and Dale Moss Relationship Timeline](https://www.lifeandstylemag.com/wp-content/uploads/2021/01/133491780_425988591887657_2133443144053388937_n.jpg?fit=800%2C892&quality=86&strip=all)
Courtesy Dale Moss/Instagram
![‘Bachelorette’ Season 16 Couple Clare Crawley and Dale Moss Split, Call Off Engagement](https://www.lifeandstylemag.com/wp-content/uploads/2021/01/Bachelorette-Season-16-Couple-Clare-Crawley-and-Dale-Moss-Split-Call-Off-Engagement.jpg?fit=800%2C800&quality=86&strip=all)
ABC/Craig Sjodin
![dale moss and clare crawley](https://www.lifeandstylemag.com/wp-content/uploads/2021/01/dalemoss13_134729534_2496904643946164_5432597047810546147_n.jpg?fit=800%2C800&quality=86&strip=all)
Courtesy of Dale Moss/Instagram
![dale moss mental health](https://www.lifeandstylemag.com/wp-content/uploads/2021/01/dale-moss-mental-health.png?fit=485%2C682&quality=86&strip=all)
Corutesy of Dale Moss/Instagram
![Clare Crawley](https://www.lifeandstylemag.com/wp-content/uploads/2020/10/clarecrawley_127637909_953563081717493_5671586181570597901_n.jpg?fit=800%2C800&quality=86&strip=all)
Courtesy of Clare Craley/Instagram
![From 'The Bachelorette' to Now! A Timeline of Clare Crawley and Dale Moss' Complicated Relationship](https://www.lifeandstylemag.com/wp-content/uploads/2021/02/Clare-Crawley-Dale-Moss-Relationship-Timeline-Clues.jpg?fit=800%2C711&quality=86&strip=all)
Courtesy of Clare Crawley/Instagram; Dale Moss/Instagram
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Courtesy of Dale Moss/Instagram
![Clare Crawley and Dale Moss Relationship Timeline Bachelorette Wearing Her Ring Again](https://www.lifeandstylemag.com/wp-content/uploads/2021/02/152915063_2911368365758614_8916181617896890485_n.jpg?fit=800%2C800&quality=86&strip=all)
Courtesy Clare Crawley/Instagram
![Rachel Lindsay Is Shocked Clare and Dale Are Back Together](https://www.lifeandstylemag.com/wp-content/uploads/2021/02/therachlindsay_123634134_189823639278043_8306057537476719835_n.jpg?fit=800%2C800&quality=86&strip=all)
Courtesy Rachel Lindsay/Instagram
![Clare Crawley Shuts Down a Hater Who Tells Her to 'Give It Up' Amid Dale Moss Reunion](https://www.lifeandstylemag.com/wp-content/uploads/2021/02/Clare-Crawley-Dale-Moss-Clapback.jpg?fit=800%2C800&quality=86&strip=all)
Courtesy of Dale Moss/Instagram
![dale moss mental health](https://www.lifeandstylemag.com/wp-content/uploads/2021/01/dale-moss-mental-health.png?fit=485%2C682&quality=86&strip=all)
Corutesy of Dale Moss/Instagram
![Bachelorette's Clare Crawley and Dale Moss Engaged Again](https://www.lifeandstylemag.com/wp-content/uploads/2021/07/Clare-Crawley-And-Dale-Moss-Engaged-Again-Feature.jpg?fit=800%2C482&quality=86&strip=all)
Courtesy Clare Crawley/Instagram
![Say It Ain't So! Fans Think 'Bachelorette' Couple Clare Crawley and Dale Moss Have Split — Here's Why](https://www.lifeandstylemag.com/wp-content/uploads/2021/01/Fans-Think-Bachelorette-Couple-Clare-Crawley-and-Dale-Moss-Have-Split-Heres-Why.jpg?fit=800%2C800&quality=86&strip=all)
Maarten de Boer/ABC; Broadimage/Shutterstock
![Clare Crawley Dale Moss Split Relationship Timeline](https://www.lifeandstylemag.com/wp-content/uploads/2021/09/clarecrawley-196416605_278250507320703_1219333949785277443_n.jpg?fit=800%2C1000&quality=86&strip=all)
Clare Crawley/Instagram