Jay Cutler Reveals He "Basically" Blacked Out While Proposing to Kristin Cavallari

By Alyssa Ray Mar 11, 2020 5:00 PMTags
Watch: Jay Cutler Blacked Out During Proposal to Kristin Cavallari

Jay Cutler and Kristin Cavallari have been married for almost seven years. Yet, the retired NFL player doesn't necessarily remember their engagement.

In this clip from Thursday's all-new Very Cavallari, Jay reveals to friends that he pretty much blacked out when he got down on one knee all those years ago. From what Jay recalls, he proposed in Cabo and it was in no way perfect.

"I didn't do it well. If I could do it again, I'd do it again," the former Chicago Bears quarterback informs Justin Anderson, Austin "Scoot" Rhodes and Mark "Chuy Block. "It's just nerve-wracking."

Unsurprisingly, Justin resonates with Jay's take on proposing, noting that he'd probably "black out."

"You basically do! It's just like, 'Get this ring out of my face. I can't hold this anymore,'" the father of three adds.

After Justin inquires if Jay cried, the Cutler patriarch makes it clear that he didn't cry, but Kristin "shed some tears."

Kristin Cavallari & Jay Cutler's Cutest Pics

Of course, Justin's many questions about proposing has boyfriend Scoot wondering if he'll pop the question soon.

"Hearing Justin ask Jay about proposing to Kristin is kinda like, getting my mind wondering, is something coming up?" Scoot ponders in a confessional. "We'll see where it goes."

We can't blame Scoot for expecting an engagement as the gang is in the Italian countryside, which is an incredibly romantic spot. Meanwhile, Jay remembers how "rough" it was asking for Dennis Cavallari's blessing.

"Asking permission from Kristin's dad, that is rough," Jay quips. "I mean, he said yes. It's fine, but just the buildup is like—I don't remember that either."

Be sure to catch this candid conversation in the clip above!

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