‘Hard As Hell’: Jay Cutler’s Struggling In The Dating Game After Divorce

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Retired NFL quarterback Jay Cutler is either an absolute genius or he’s really down and out in the dating game after his divorce from actress Kristin Cavallari. The 38-year-old Cutler fired up his podcast this week and declared he’s having dating problems.

“It’s hard as hell really,” the Bears legend said on “Uncut with Jay Cutler.” The father of three then went on to explain what dating is like in 2021.

“Meeting people is hard. I think finding out what people really want from you; I think that’s probably an issue.”

Then Jay went on to say that his “priorities have changed,” and “it isn’t just a purely selfish play” now with his relationships. He has kids to think about!

This is an absolutely genius calculated move from Cutler. This is Jay telling all the recently divorced Nashville moms to step on up, but they need to know Jay’s at that stage of life where he wants to be on the couch at 10 on Friday nights and wants to hit up farmer’s markets on Saturdays.

As for where Jay’s going to meet ladies that fit his criteria, he’s clearly looking in all the wrong places.

“There are apps, there’s Twitter, there’s Instagram, it’s a whole different ball game,” Cutler continued. “You’re not just walking into a restaurant or bar and talking to somebody. That doesn’t exist anymore.”

Hold up, Jay. I hope this guy’s not trying to pick up women in the cesspool that is Twitter.

Here’s my dating advice for Jay:

• Patio parties at Jay’s farm. Invite some couples and tell them to invite fun single friends. Invite the neighbor who’s like 60 but knows how to hang with people in their late 30s. Invite people who aren’t the least bit connected to sports or entertainment. Invite nurses. Invite x-ray techs. Tell your trusted married friends to mix in a loan originator and a dental hygentist.

• Now, these don’t have to be formal bashes that are going to be turned into Instagram content. I’m talking very informal. At least one neighbor should be wearing a shirt with cutoff sleeves.

• Bring your own booze. This means people are bringing their own coolers which means sharing. Oh look what Brittany brought…JELL-O SHOTS!

• This isn’t a blackout event. This is just people being people. No bar scene. No drama on Broadway. The start time should be around 1 p.m.

• Hire a local BBQ pitmaster with a big beard to cook up the food

• Create competition; I need to see cornhole boards or volleyball courts. I want to see brackets. Pick coed teams.

• These parties should be held once a month and when it’s Kristin’s weekend with the kids.

I guarantee Jay will find 8-10 dates out of one of these events. He might end up going to a minor league baseball game with a dental hygentist and her two kids, but at least he’ll already know she’s fun and can pound a volleyball.



Written by Joe Kinsey

Joe Kinsey is the Senior Director of Content of OutKick and the editor of the Morning Screencaps column that examines a variety of stories taking place in real America.

Kinsey is also the founder of OutKick’s Thursday Night Mowing League, America’s largest virtual mowing league.

Kinsey graduated from University of Toledo.


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