Jon Lovett and Ari Schwartz Explained: What Actually Happened With the Crooked Media Romance

If you’ve been listening to Pod Save America or Lovett or Leave It for a while, you know Jon Lovett isn’t exactly a "low-key" person. He’s the guy who turns a 30-second ad read for bedsheets into a ten-minute existential crisis about late-stage capitalism. So, when the internet started whispering that he was dating a coworker named Ari Schwartz, the "Friends of the Pod" community basically lost its collective mind.

The speculation turned into reality in early 2025. It wasn't just a rumor anymore. It was an engagement.

Who is Ari Schwartz, really?

Look, if you Google the name "Ari Schwartz," you might get a little confused. You'll likely see a cybersecurity expert who worked for the Obama administration. That is not the Ari Schwartz we’re talking about. Honestly, it would be a very Lovett-esque twist to date a high-level government hacker, but the truth is a bit more "office romance" than "international espionage."

The Ari Schwartz in question is the Chief of Staff at Crooked Media.

They aren't just some random person Jon met on a dating app. They've been a pillar of the company for years. Ari started at Crooked back in 2021 as a programming and production coordinator. They moved up the ranks quickly—Senior Programming & Production Manager, then finally Chief of Staff in 2023. Before that? They worked for Alexandria Ocasio-Cortez’s congressional campaign.

Basically, Ari is the person who keeps the trains running on time while Jon is busy recording podcast episodes about why he hates the OceanGate submersible or the Iowa Caucuses.

The "Survivor" Moment and the Big Announcement

You remember when Jon disappeared into the jungle for Survivor? Most of us thought he was just doing it for the "bit" or to see if he could survive a week without a Twitter feed.

Turns out, that time apart was the catalyst.

In March 2025, the couple finally made it official. On an episode of Lovett or Leave It, Jon dropped the news with his signature mix of sincerity and sarcasm. He joked about being "engaged several years ago" (a nod to his high-profile past) before confirming that "someone finally chose not to Leave It."

Schwartz later shared that Jon being in Fiji for five weeks without a phone made them both realize there was no reason to keep waiting. It’s funny how a reality TV show about starving on an island can clarify your relationship goals.

A Fresh Start After Ronan Farrow

We have to address the elephant in the room. For over a decade, Jon Lovett was one half of a massive power couple with investigative journalist Ronan Farrow. They were engaged. They were the "it" couple of the intellectual left. When they broke up in late 2022, it felt like a divorce for a certain segment of the internet.

Lovett was single for a while. He talked about it on the pod—the awkwardness of dating in your 40s, the "liminal space" of being publicly associated with an ex while trying to move on.

Dating Ari Schwartz marks a huge shift. It’s a move from a very public, high-glamour partnership to something that feels a bit more grounded. Ari uses they/them pronouns, and Jon has spoken movingly about how his partner’s identity has shaped his own perspective on the current political climate. He’s admitted that while he’s incredibly happy—maybe for the first time—he’s also "motivated by rage" at the way trans and non-binary people are treated in the U.S.

The Workplace Dynamics

People always get weird about workplace relationships. You've probably seen the Reddit threads. "Is it okay for a co-founder to date the Chief of Staff?"

It's a valid question. However, by all accounts, the relationship developed long after Ari was established in their executive role. In a company like Crooked Media—which is basically a tight-knit group of former Obama staffers and their friends—the lines between "work" and "life" have always been pretty blurry.

They even played a version of "The Newlywed Game" (rebranded as the Soonie-Wed Game) on the show against Tig Notaro and Stephanie Allynne. It was chaotic. It was sweet. It was very, very gay.

What’s Next for the Couple?

The wedding isn't going to be some quiet, secret affair. Lovett has already joked that a small wedding is "a lie" and that for "gays and theys," a big wedding is basically an act of resistance.

So, expect a spectacle.

What You Can Take Away From This

If you're following this story, it's not just about celebrity gossip. It's about a few real-world things:

• Resilience after long-term breakups: It’s possible to find something entirely different and equally fulfilling after a decade-long relationship ends.
• The "Workplace Transition": Navigating professional and personal boundaries requires a massive amount of transparency, especially when you’re in the public eye.
• Authenticity in Media: Lovett’s choice to be open about his partner’s trans identity isn’t just personal; it’s a political statement in 2026.

If you want to keep up with them, the best place isn't actually Instagram—Jon barely posts. Your best bet is listening to the closing segments of Lovett or Leave It on Saturday mornings. That’s where the real updates usually slip out.

Keep an eye on the "Friends of the Pod" Discord and the Crooked Media events page. If there's a live show coming to your city, there's a 90% chance Ari is backstage making sure Jon doesn't wander off, and a 10% chance they’ll end up on stage for a bit.