Dale and Clare got engaged on the finale of her The Bachelorette season, but his representative announced the former pro athlete's split from Clare in early October 2021. (However, Dale and Clare had reportedly already broken up in September).
Dale, sporting a Burberry button-up shirt and black pants, was reportedly all smiles with Florencia, who was wearing a black trench coat and tall leather boots.
He was carrying a brown paper bag in his hand as the pair strolled side by side, and at one point, they had their arms intertwined.
According to a source, Dale and Florencia "are hooking up and it's casual."
The source added of the two models -- who are both represented by EWG Management -- "They are not dating."
Clare, 40, took to Instagram earlier this month and posted a video featuring her weekend full of events and fun in Indiana with Blake, a 31-year-old male grooming specialist from Phoenix, AZ.
"Went for business, left with the most unexpected remarkable memories! Indy, you were truly beautiful and exactly what my soul needed," Clare captioned her post.
In the video, Clare and Blake apparently went shopping in clothing boutiques and garden stores. They also had fun duckpin bowling, singing in the car together, and playing with Blake's niece and nephew.
Blake -- who had a brief fling withTia Booth on Bachelor in Paradise's seventh season last summer -- also posted an Instagram Story that weekend. He was beaming ear to ear as he tightly wrapped his arm around Clare.
Clare allegedly blocked Dale after he had flown to her home in Sacramento, CA, on September 28 but left the following day for "a work obligation," which turned out to be a fitness event with The Bachelorette alum Tyler Cameron.
Clare apparently needed Dale by her side as her mother's condition with dementia and Alzheimer's worsened. (Clare's mom was later placed in hospice care).
Following the October announcement of their breakup, Clare threw major shade at Dale on more than one occasion. She ultimately thought he was fake and had put on a performance during their romance so he could achieve fame and boost his acting and modeling career.
Clare previously told Jana Kramer in a late October episode of the "Whine Down" podcast her "biggest regret" from The Bachelorette is "trusting a man," People reported.
"I trusted somebody, I believed somebody that they were who they said they were or that they would hold up to the promises that they make when they get down on one knee... [But] I don't regret that I loved loving him," Clare said at the time.
Prior to their latest split, Clare and Dale had called it quits on their engagement once before in January 2021, which totally "crushed" Clare.
Multiple sources had described Dale as a "fame-seeker" and partyboy in New York City while Clare had been very clear from the start about her intentions to get married, settle down and have children in the near future.
Reports also swirled at the time Dale had cheated on Clare, although Dale firmly denied the cheating allegations.
In regard to rumors Dale had "hooked up" with Abigail Heringer before her stint on Bachelor in Paradise's seventh season this past summer, Clare acknowledged breakups "can get very messy and very icky."
"I always try to err on the side of taking the high road, even when there are a lot of things I could say," Clare explained last year.
She suggested on Jana's podcast that Dale's dreams were based "on being in the public eye," adding, "It's very impersonal to be putting out statements and articles. I think you both know the truth. I know the truth, he knows the truth."
Clare also apparently took shots at Dale in a September 30 Instagram post, although she didn't name Dale directly.
She hinted Dale had put on an "act" and created a narrative about their relationship and its demise.
Clare also tagged Abigail in her post -- which suggested Clare believed the Dale and Abigail rumors -- and thanked people who love her unconditionally and for "no personal gain, ESPECIALLY WHEN THE CAMERAS ARE OFF with no accolades."
However, a source close to Dale told Us last year that Dale and Abigail "never kissed or had sex" and they were just "friends" after meeting at a flag football game in New York City.
Clare, on the other hand, told Jana that she knows what "happens behind closed doors."
"When you know the truth... I don't care for my side of the story, to be honest, to even be out there, even if I have receipts and proof, everything I need to show that I could really put it out there," Clare shared, according to People.
Not only was Clare dealing with a broken heart and her mother's health crisis in the fall, but she was also still recovering from having her breast implants removed.
"There was a lot on my plate... It all came crashing down at once," Clare noted.
Clare also said it was "painful" that she and Dale had never talked things out or found closure at the end of their hot-and-cold romance.
"The one that gets me is, how do you say goodbye to somebody you never wanted to walk away from?" Clare reportedly said through tears.
"Like I would have never walked... You're having to say goodbye to somebody you don't want to be saying goodbye to, you have to walk away from somebody you don't want to walk away from. It's hard, it's painful."
Before his outing with Florencia, fans questioned if Dale was dating blogger Thania Peck when the pair was spotted attending The King's Man premiere together in December 2021.