Sydney Sweeney & Scooter Braun's Relationship Is Full Of Glaringly Obvious Red Flags

Rumors of romance first started swirling around controversial actor Sydney Sweeney and despised music mogul Scooter Braun when they were spotted strolling the streets of Venice, Italy, together while in town for Jeff Bezos and Lauren Sanchez's wedding. Suffice to say, Sweeney's flirty behavior at the Bezos-Sanchez wedding caused quite the stir. "Syd was intrigued — Scooter's a charmer. He's confident, but also sweet and very attentive," a source told People about Sweeney and Braun's destination wedding meet-cute, painting a different picture of the man who almost bought OnlyFans.

Since then, things have seemingly gotten pretty hot and heavy between the celebs, with the high-profile couple spending Thanksgiving together at her mansion in the Florida Keys. "Things are getting serious and it's very real," a source told Us Weekly. "Neither of them expected it to turn into something serious at first and are surprised by how genuine the connection has become."

Unfortunately, this budding relationship has quite a few glaringly obvious red flags. That may be what's actually appealing to Sweeney, who seems to have some undiagnosed daddy issues, considering her penchant for dating older men; there was a 14-year difference between Sweeney and her former fiancé, Jonathan Davino, while 16 years separates her from Braun. At least Sweeney seems self-aware about it, saying during a Fandango interview, "Honestly, I've been learning that I like a circus. Just a bunch of red flags." Between Sweeney's very own runaway bride moment to Braun's rumored ruthless business tactics and his brutal divorce, those red flags are furiously flapping in her face.

Sydney Sweeney caused quite the commotion in March when it was reported that she had called off her wedding to fiancé Jonathan Davino. While there was much speculation as to why she pulled the plug on her partnership, rumors had it that she was feeling overwhelmed by everything. It wasn't until a couple of months later, however, that Sydney addressed the breakup herself. "I'm learning a lot about myself, spending more time with my friends. And I'm loving it," she told The Times in May after acknowledging that she was single.

Making things even more awkward, both Davino and Sweeney remain business partners of Fifty-Fifty Films, a production company they co-founded in 2020. While Davino maintained that he and Sweeney remained friends, he admitted to The Daily Mail that things were "complicated," which seemed like an understatement.

In November, many months after Sweeney and Davino had called it quits and at the peak of Sweeney's budding romance with Scooter Braun, Sweeney was photographed hiding out in the passenger seat of Davino's car after a night out. Things between the exes eventually took a more contentious turn during the secret car meet-up. Sources told The Daily Mail that they overheard the "Anyone But You" actor screaming, "I don't believe you. Please leave, leave me alone," at the top of her lungs. Yikes. Interestingly, the spectacle hasn't seemed to affect Sweeney's relationship with Braun in the slightest, considering their romantic Thanksgiving break together in the Florida Keys.

While Sydney Sweeney has fueled her own controversies by possibly pandering to the far-right, to the extent that many celebrities want nothing to do with her, we would be absolutely remiss not to discuss the shady side of Scooter Braun. As you may recall, in June 2019, a self-professed "sad and grossed out" Taylor Swift blew the lid off of Braun's perfectly curated reputation all in one fell swoop, after she found out he had secretly purchased the master recordings of her discography behind her back. "All I could think about was the incessant, manipulative bullying I've received at his hands for years," she penned in the viral Tumblr post.

Swift went on to note all the ways in which Braun continuously bullied her, including the time he and two of his clients, Justin Bieber and Kanye West, harassed her on Instagram. She continued, "Any time Scott Borchetta has heard the words 'Scooter Braun' escape my lips, it was when I was either crying or trying not to. He knew what he was doing; they both did. Controlling a woman who didn't want to be associated with them." Alexa, play "Vigilante S***" by Taylor Swift.

Ironically, since then, Braun has also had falling outs with both Bieber and West, not to mention Todrick Hall, who left Braun and wrote on X (via Billboard), "He is an evil person who's only concern is his wealth and feeding his disgusting ego. I believe he is homophobic." Braun reaped what he sowed, earning his reputation as one of the most despised people in the industry. "I don't think you can pretend to be the nice guy on social media but, behind the scenes, be one of the most cutthroat people in the business," one industry insider told Business Insider for a piece that was fittingly titled, "The Many Faces of Scooter Braun."

All's fair in love and war divorce, we suppose. From the outside looking in, it appears that Scooter Braun's brutal business tactics have a way of spilling over into his personal life, as well. Braun and his ex-wife, Yael Cohen, were married for seven years and welcomed three children together before Braun officially filed for divorce in July 2021; it was later finalized in September 2022. 

In the end, Braun proved to be just as shrewd in his divorce dealings as he was with Taylor Swift's masters. According to divorce documents obtained by People, Braun walked away with joint custody of the children, the $65 million mansion he purchased after their separation, as well as many other residences, more than 100 pieces of artwork, a 2018 Porsche Cayenne GTS, a 2019 Tesla Model X, several golf carts, an electric scooter, and the couple's private jet. No doubt, Braun's apparent divorce win was largely due to his purported air-tight prenup and bulldog celebrity divorce attorney, Laura Wasser, as his counsel.

Braun did give Cohen a $20 million settlement, but that's not exactly a windfall for him; Braun's net worth is higher than you think, with estimates putting it near an eye-popping $1 billion as of December 2, 2025. Simply put, Cohen's settlement pales in comparison to the fortune that Braun sits on. Sydney, sweetie, don't forget that prenup.