The Bachelor Nation alum, 40, and Money From Strangers star, 38, were spotted at a Los Angeles Lakers basketball game together on November 2. The comedian then attended an event for Alo Yoga with Clare, which they both documented on their personal Instagram accounts. The pair are also following each other on the social media platform.
Prior to Clare, Jeff had a fling with The Hills alum Kristin Cavallari following the Uncommon James founder filing for divorce from estranged husband Jay Cutler. Us Weekly reported they split in March.
As for Clare, she and Dale, 33, had been navigating through their on-and-off relationship since getting engaged on season 16. The reality TV couple caused quite a stir when the former football player popped the question midseason, and they left the show together, causing Tayshia Adams to step in as the new Bachelorette.
Dale announced their first split in January, but Clare released a message days later that made it seem like their uncoupling was less than amicable.
“I was made aware of a ‘mutual’ statement at the same time you all were, so I’ve needed some time to really digest this,” she wrote via Instagram. “Speaking for myself, my intentions with this relationship have always been very clear, so the truth is I am crushed.”
However, the duo quietly rekindled their romance, and Us Weekly confirmed in February they were back together. Multiple outlets reported months later that their engagement was even back on as they rebuilt their relationship.
Things ended for good between Clare and Dale in September. A rep for the South Dakota native claimed to E! News that the exes reunited “weeks” after their split when Dale flew out to Sacramento because the health of Clare’s mother began to decline.
“Dale flew to Los Angeles for a work obligation and had every intention to travel back to Sacramento to be with her,” his rep said. However, Dale did not return to Northern California, because, the rep alleged, “His number was blocked, which made it impossible to communicate with Clare.”
While the hairstylist didn’t directly respond to these claims, she stirred rumors that Dale had previously hooked up with Bachelor in Paradise alum Abigail Heringer. She also shared a cryptic message via Instagram.
“It takes a lot to bring me to my knees,” Clare wrote at the time. “But damn, this week has pushed me to that point. One thing I refuse to do though is stay down. I’ll be dammed if I let it all take me out. So, amidst all this, I’m taking steps even if the [sic] are small.”