"Very Perceptive" Jay Cutler Transforms Into a Dating Coach for Kristin Cavallari's Best Friend

By Alyssa Ray Mar 25, 2019 3:00 AMTags
Watch: "Very Cavallari" Recap (S2 Ep4): You Can't Ship With Us

Who knew Jay Cutler was a budding dating coach?

On Sunday's all-new Very Cavallari, Kristin Cavallari headed to Los Angeles with Brittainy Taylor for the opening of their Uncommon James pop-up in Los Angeles. Thus, with the Very Cavallari star out of town, her spouse took it upon himself to fix best friend Kelly Henderson's love life.

"I feel like there's a lot of complaining and what ifs between you guys and what you're gonna do," Jay informed Kelly and Kristin ahead of the latter's trip. "I think you just gotta get out there and do it."

While The Hills alum felt that Kelly has been putting herself out there, the retired quarterback noted that the stylist only dates those in her "little bubble" and "little circle." Thankfully, the father of three had a solution for Kristin's longtime gal pal.

"Here's the thing! I've got a lot of free time at night, because my boss goes to sleep at 8," Jay quipped. "So, we start going out. We hit the town, we go to some adult places."

Kristin Cavallari & Kelly Henderson's Fun BFF Moments

In fact, Jay was more than happy to be Kelly's wingman as he already knew what type of suitor to look out for. "Someone that's confident in who they are," the American athlete rattled off. "Someone who's independent, has their own thing going on. I mean, he's got an artistic streak to him."

Although Jay envisioned Kelly dating a man that "leans towards skinny jeans," he believed a beau with a corporate job could be in the cards.

"Oh wait! Jay just described the most perfect human being on the planet," Kristin joked in a confessional. "No s--t, Jay! Kelly wants him and me too!"

Even though Kristin was skeptical of Jay's plan, Kelly agreed to step out with her new dating coach. During an outing to a bar, Kelly revealed that work had been too hectic for her to prioritize a love life.

"You couldn't prioritize a drink?" the Cutler patriarch asked.

According to Henderson, "dating to date" has completely lost its appeal. "Okay, we're not dating to date! We're meeting people," Jay advised. "You are meeting for a drink to see, 'Alright! Do I want to go on a date with you? Do I want to take the next step and get to know you?'"

In order to get Kelly out of her bubble, Jay suggested that she try a dating app—and Kristin's bestie was pretty opposed to the idea. Nonetheless, the former footballer was able to convince Kelly to try her hand at online dating.

"The course that you're on, you're gonna meet X amount of guys," Jay relayed. "The course that we're trying to get you on? We're gonna meet 10X. We're just using a platform to meet more guys."

Watch: Jay Cutler Wants Kristin to "Cut Off the Head of the Snake"

In a matter of time, Kelly signed on to Jay's plan, especially since the 35-year-old dad agreed to run the app for her.

"I feel fabulous about Jay running my dating app," Kelly noted to the Very Cavallari cameras. "I do think that he is a very perceptive, intuitive person. So, I honestly trust Jay's judgement."

While Jay had a handle on things at home, Kristin was busy overseeing more drama with Uncommon James. Just as Kristin left Nashville to open the Los Angeles pop-up, unpopular store manager Kaylee made her return.

Despite telling her employees to essentially suck it up, the UJ crew clashed with Kaylee during Cyber Monday. Specifically, after Brittainy and Kristin were informed that there was (yet another) shipping crisis, the twosome tasked Kaylee with getting the staffers into shape.

"This is everybody's Christmas gifts! I'm not having someone open an empty box for Christmas," Brittainy snapped on the phone. "If they're not gonna take it seriously, than they're gonna go home."

See everything else that went down on this week's episode, including footage of the ongoing drama at Uncommon James, in the recap video above!