Kristin Cavallari & Jay Cutler Crack Up Watching Kelly Henderson's Blind Date Go "Down in Flames"

Pop! There goes Kelly Henderson‘s mediocre blind date.

“Have you always wanted to be an actor?” Kristin Cavallari‘s BFF warily asked Jared—the part-time Axe model, part-time CrossFit trainer who Jay Cutler‘s friend Mark “Chuy” Block set her up with—during Sunday’s new Very Cavallari. Ten seconds later, Kelly wished she hadn’t brought it up in the first place.

“No, I didn’t take an acting class until my last year of college,” Jared replied. “And I took it because I had friends tell me that it was an easy A, it was a class full of women and ‘You basically need some exercises.'”

At that, Kelly offered up a polite “Sounds great.” But her recently appointed dating coach saw right through it. “This thing is basically going to go down in flames,” Jay told his wife, while both halves of the married couple observed from across the bar. Kristin took a considerably more passive approach to her voyeurism.

“I need popcorn,” quipped the Uncommon James founder, pretending to swallow a few handfuls’ worth without ever looking away from her pal. 

To no one’s surprise, Jared didn’t exactly sweep Kelly off her feet. “I literally would ask him a question and he would answer and then never ask me a question about me,” the blogger and stylist told Kristin the next day. “He’s a model,” her friend sighed. “What can you do? It’s all about them.”

Even though Jay and Chuy struck out as Kelly’s wannabe love doctors this week, the football pro did lend his support to Kristin, who was understandably in a bit of a funk after spending the 3-year anniversary of her brother Michael‘s passing with family in Southern California.  

“Last time I was in Laguna Beach, it was for my brother’s memorial service,” she told the camera. “It’s weird going back just because every time in the past that I would be in Laguna, I would always see my brother. So, this is the first time I’m going back and he’s not there.”

After having lunch with her dad Dennis Cavallari and reminiscing about the reality star’s early days as an MTV villain, Kristin asked him how he’s doing, in light of the occasion. “I’m doing OK,” Dennis assured her. But his daughter worried he was just putting on a brave face while she was in town.

“I think he’s sort of afraid to be really vulnerable in front of me. But I know that he’s hurting, big time,” she told her husband once she’d returned to Tennessee, acknowledging that losing a child would be “the worst thing in the entire world.”

Of course, Jay understood. “It’s not supposed to happen like that,” he agreed, before gently advising his wife to try and “concentrate on the good stuff” around her if she can. Their conversation ended in a heartbreaking final moment. Seconds after she’d left the room, Jay heard Kristin sobbing quietly in the hallway of their Nashville mansion. When he walked over to her, she buried her face in his shoulder and cried.

Back at the store, Kristin’s employees were munching on popcorn too. Or at least one or two of them, anyway. In the wake of last week’s shipping drama, the UJ boss had seen more than enough less-than-professional behavior from the likes of her staff.

“The culture at Uncommon James has become really catty and just quite frankly immature,” Kristin said, calling out the burgeoning tension between newly-rehired store manager Kaylee and veteran employee Colby. Their boss’ surprise talking-to at the warehouse one afternoon—when Kristin plainly informed everyone that they’d better shape up or head home—had the whole office stressed out.

Well, except for Matt, the store’s former head of shipping who’d already paid the price for his own package-related blunders on Cyber Monday.

“I’m excited because for once, I’m not the witch that’s being burned at the stake. So, light it up baby!”  he told the camera later with a grin. “So you’re like actually eating the popcorn now,” noted fellow UJ employee Reagan, and it seemed Matt couldn’t have said it better himself. “I’m eating the popcorn for once!” he agreed.

See how things eventually panned out between Kaylee and Colby in the full recap video above!

Watch the premiere of Very Cavallari 15th July at 8 p.m., only on E!


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