Controversial Podcaster Theo Von Gets Brutally Rejected Live On Air After He Tries To Flirt With Reporter

Controversial podcaster and part-time flirt Theo Von learned the hard way that College GameDay isn’t The Bachelor.

It happened last Saturday when ESPN host Jess Sims wrapped up a segment with Von, who was a guest picker predicting college football matchups alongside the show’s regular analysts.

Jess smiled and said:

“The guys are ready for your second round of picks, so go ahead. Right up there.”

For context, Sims—a Peabody, Massachusetts native—joined ESPN in 2022 as a sideline reporter covering college football and men’s basketball. She’s also a Peloton fan favorite and a contributor to Good Morning America.

So, naturally, Theo shot his shot:

“Oh, I’m already going? Will I ever see you again?”

Points for confidence. Minus several for timing.

And without missing a beat, Ms. Sims said, “Oh, I hope not!” and professionally waved him off. Von let out a small, defeated “Aww,” and trudged dejectedly stage left.

You can watch the aww-kward moment below:

ESPN should change its name to ESPN-N-O-P-E.

The on-air rejection capped off a rough stretch for the still-single comedian. Just weeks ago, Von went viral after joking that Vanderbilt quarterback Diego Pavia had offered him a date with his mom if the Commodores beat South Carolina.

And fortunately—or maybe unfortunately for Mom—the Commodores did win, 31-7, and Von took the “W” a little too literally.

In the post below, Von even shared a photo of Pavia’s mother, Antoinette Padilla, to X with a heart drawn around her face:

Unfortunately, his professional record has been less victorious. During the taping of his upcoming Netflix stand-up special at New York’s Beacon Theater, fans said Von appeared unprepared and distracted. About a third of the audience reportedly left before the show ended, with some expressing concern after he mentioned he was “trying not to take [his] own life.”

Von later addressed the disastrous night on his This Past Weekend podcast:

“It’s part of the job. The first ten years of doing comedy is failure. So much of my life—the best things that have ever happened in my life—have been on the other side of failure.”

Still, Von’s recent woes aren’t just personal. He found himself unexpectedly at the center of a political controversy after the Department of Homeland Security used one of his clips to promote the Trump administration’s deportation campaign.

The DHS propaganda video using Von’s clip can be seen in the CNN report below:

- YouTubeCNN

Can you even imagine making an insensitive joke—and waking up one day to find you’ve been unexpectedly cast in a deportation ad? Welcome to Trump 2025, bro.

Von quickly condemned the use of his content, posting (in a now-deleted X post):

“My father immigrated here from Nicaragua. One of my prized possessions is his immigration papers from when he came here — I have them framed… So I have tons of thoughts about [immigration]... This was just f---ed up.”

According to Von, the viral clip even prompted a “high government official” to contact him about additional security—an offer he declined.

Even with all his political and comedy chaos, social media went feral over the ESPN rejection—pure secondhand embarrassment in HD.

Von—full name Theodor Capitani von Kurnatowski III—has long occupied a strange space between pop-culture shock jock and conservative-curious commentator. Though he’s interviewed Donald Trump and backed parts of his agenda, he’s also criticized other elements—from mass-deportation plans to the handling of the Epstein files.

Trying to walk that tightrope, he once said:

“I’m all for tighter borders... I’m all for knowing who is in a country.”

Somehow, that statement manages to say everything and nothing at the same time.

But he’s also called Israel’s actions in Gaza “one of the sickest things that’s ever happened,” drawing backlash from both sides of the aisle.

Born and raised in what he affectionately calls the “stray-animal belt” of Louisiana, Von emancipated himself at 14 and first found fame on MTV’s Road Rules: Maximum Velocity Tour and The Challenge.

He later won Comedy Central’s Reality Bites Back against Amy Schumer and Tiffany Haddish, hosted the hidden-camera show Deal With It, and even appeared in The Tomorrow War alongside Chris Pratt.

At this point, Von’s politics, jokes, and timing all have one thing in common: they’re not landing.