Since their Venice encounter, the duo’s relationship has intensified, with the couple spending Thanksgiving at Sweeney’s luxurious home in the Florida Keys. “Their connection has deepened significantly,” a source shared with Us Weekly. “Neither anticipated their bond would grow so strong, and they are genuinely surprised by how authentic it feels.”

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.”

In March, Sweeney made headlines when she reportedly ended her engagement to Jonathan Davino. The split fueled speculation, with many suggesting she was overwhelmed by the situation. Sweeney finally addressed the breakup a few months later. “I’m discovering a lot about myself, enjoying more time with friends, and I love it,” she shared with The Times in May, confirming her newly single status.

In an intriguing twist, Sweeney was seen in November in the passenger seat of Davino’s car after a night out, leading to a tense exchange between the exes. Witnesses reported to The Daily Mail hearing Sweeney yell, “I don’t believe you. Please leave, leave me alone.” Despite the drama, Sweeney’s romance with Braun appears unaffected, as evidenced by their romantic getaway over Thanksgiving.

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.