Kelly Henderson and Jay Cutler on Season 2 Premiere

Kelly Henderson and Jay Cutler on Season 2 Premiere

Jay Cutler Gives Kelly Henderson Dating Advice on ‘Very Cavallari’

Jay Cutler is playing dating coach to Kelly in season 2 premiere of Very Cavallari.

In an all new season 2 premiere of Kristin Cavallari’s reality show on E! her former NFL husband, Jay Cutler is dishing the dating advice.

We saw in season one how hard it was to really win Jay over but Kristin says, “I think I have just a couple of friends that Jay really loves, and Kelly is one of them,” referring to her lifestyle blogger Nashville based friend.

How did Kelly’s Date Go?

When Kristin’s BFF, Kelly stops by the house, Kristin can’t help but to ask how her date was, “Didn’t you go on a date the other night?

Jay’s ears perked up asking, ‘with who?

With this guy I’ve kind of had a crush on, we’ve just been hanging out talking,” she said.

Kelly admitted that they are at different points in their lives where he just wants to have fun and not get too serious.

Girls, haven’t we all been there?!

(On a side note – It appears Kristin is cooking from her own True Roots Cookbook in this scene that you can see open on her kitchen counter.)

Kristin Cavallari Cooks in Nashville Kitchen
Kristin Cavallari Cooks in Nashville Kitchen | Very Cavallari

As Kristin seamlessly navigates her way around her new Nashville kitchen, she interjects, “how old is he?

35!” Kelly exclaims.

I mean, at what point does that get old?” says the former “The Hills” star.

They look to the man in the room for some wise dating advice.

Jay Cutler Gives Kelly Henderson Dating Advice on 'Very Cavallari' Season 2
Jay Cutler Gives Kelly Henderson Dating Advice on ‘Very Cavallari’ Season 2 | Very Cavallari

Jay’s Dating Advice

In typical guy fashion he says he doesn’t see what the problem is with the guy wanting to have some fun. His wife jumps in, “Kelly is looking for her husband, she doesn’t have time for this.

I don’t understand why you guys can’t date somebody and naturally let it turn into more,” he tells Kelly.

To see the full convo and Jay’s dating advice – check the clip out below!

Tune into ‘Very Cavallari‘ on E! Sundays at 10pm starting March 3, 2019.