Sydney Sweeney Fiance: The Chicago Businessman and Why They Finally Split

Sydney Sweeney Fiance: The Chicago Businessman and Why They Finally Split

Honestly, trying to keep up with Sydney Sweeney’s love life lately has been a total whirlwind. One minute she’s the internet’s favorite "it girl" with a massive diamond on her finger, and the next, she’s basically confirming she’s flying solo. If you’ve been Googling who is sydney sweeney fiance, you’ve probably seen the name Jonathan Davino pop up a thousand times. But here is the thing: as of early 2026, he’s actually her ex-fiance.

The two had a massive, six-year run that mostly happened behind closed doors. They were the rare Hollywood couple that didn't post every single brunch or vacation on Instagram. But even the most private stories have a way of ending, and for Syd and Jonathan, that end came in March 2025.

So, Who Exactly Is Jonathan Davino?

First off, let’s clear up the weirdest rumor that just won’t die. For years, people claimed Jonathan was some big-time restaurateur or the heir to a massive pizza empire in Chicago. Sydney actually went on the record with Glamour UK to shut that down, basically saying, "I have no idea where that came from."

He’s a businessman. Plain and simple.

Jonathan is from Chicago and is roughly 13 years older than Sydney (he’s about 42 now). His family is tied to some serious tech and packaging companies like 14th Round and Final Bell. He’s not an actor. He’s not a singer. He’s a guy who works in the background, which is exactly what Sydney said she wanted. She’s been pretty vocal about the fact that dating people in the spotlight is just... a lot. By dating someone "normal," she felt she could just be "normal Syd."

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The Relationship Timeline

They started hanging out way back in 2018. They were first spotted at an Emmys party, and things just sort of clicked. By 2022, the rumors went into overdrive when she was seen with a massive rock on her left hand.

It wasn't just a romance, though. They were legit business partners. Jonathan helped her start her production company, Fifty-Fifty Films. He even got a producing credit on her hit rom-com Anyone But You. It’s gotta be weird to produce a movie where your fiancé has insane chemistry with Glen Powell, but by all accounts, Jonathan was super supportive of her vision.

The Ring and the Wedding That Didn't Happen

Let's talk about the sparkler. It was a four-carat round brilliant-cut diamond set on a rose gold band. Experts estimated the thing was worth around $150,000. It was classic, elegant, and very "her."

For a while, everyone thought a May 2025 wedding was a sure thing. But then, the signs started showing up. The ring disappeared from her finger in photos. She deleted a New Year's Eve photo of them kissing. In May 2025, during an interview with The Times, she was asked point-blank if she was planning a wedding. Her answer? A very blunt "No."

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Why Did They Break Up?

It wasn't some dramatic cheating scandal, despite what the TikTok detectives wanted to believe about Glen Powell. Sources close to the actress told People that she was just feeling "overwhelmed."

Look at her career. She’s everywhere. Euphoria, The White Lotus, Anyone But You, Immaculate—the girl doesn't sleep. The pressure of a massive Hollywood career combined with planning a life with someone 13 years her senior reportedly became too much. The split was reportedly about her wanting to focus on this "magical" moment in her career rather than settling down before she was ready.

"She's not ready to settle down. They didn't split because there is no love. They split because she just wants to focus on her career right now." — Source via People

The New Chapter with Scooter Braun?

Since the split, things have gotten even more complicated. By late 2025 and into January 2026, Sydney has been heavily linked to music mogul Scooter Braun. They were reportedly seen getting cozy at Jeff Bezos’ wedding in Venice and have been spotted around LA.

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There’s a 16-year age gap there, which has definitely raised some eyebrows. Even more recently, there were rumors floating around about her and soccer star Christian Pulisic, but he basically told everyone to stop making things up.

What We Can Learn From Syd’s "New Era"

Sydney Sweeney is basically the poster child for the "workaholic" era. She’s bought her own houses, funded her own projects, and is making it clear she doesn't need a "restaurateur" (or anyone else) to pay her bills.

If you're following her story, here are the takeaways:

  • Privacy is a choice: Even at the height of her fame, she kept a six-year relationship mostly off the grid.
  • Career vs. Personal Life: Sometimes, you have to choose. She chose her "magical career," and honestly? Respect.
  • Don't believe every TikTok rumor: The Glen Powell stuff was just great marketing, guys.

What to do next: If you're looking for more updates on her upcoming projects like Euphoria Season 3 or her next production, keep an eye on her official Instagram. Just don't expect to see many "soft launches" of new boyfriends anytime soon—she’s keeping us guessing for a reason.