A Look At Sydney Sweeney And Glen Powell's Relationship Histories

Hollywood has a long history of celebrities leaving their significant others for a co-star. For example, Billy Bob Thorton ditched Laura Dern for Angelina Jolie after filming "Pushing Tin" with her. Jolie later filmed "Mr. & Mrs. Smith" with Brad Pitt — who divorced Jennifer Aniston and began dating Jolie. Sydney Sweeney and Glen Powell's romantic comedy "Anyone But You" began garnering comparisons to Jolie and Pitt's spy film on Twitter in April 2023. Why? Because the internet's elite team of PDA private investigators became convinced that Sweeney and Powell had also made a love connection. The speculation about their off-screen flirtations reached such a fever pitch that The New York Times even weighed in on the topic.

Neither Sweeney nor Powell were single when they started filming "Anyone But You," but we'll get to that later. In charting their relationship histories, we're starting from the beginning. Sweeney once told C magazine that her teenage dating experience was a disaster, in part because she was going through a rebellious phase. "The acting-out Syd tried to find love through boys. I got myself into sometimes really unfortunate and even dangerous relationships," she said. As for Powell, he told Glamour that one of his earliest kissing experiences was beyond mortifying. "I got too excited and came in too fast, too hot, and broke the girl's nose," he recalled. But he and Sweeney both survived those awkward years and improved their dating game in the years leading up to their fateful movie meeting.

In November 2017, it was reported that Sydney Sweeney was joining the Season 2 cast of "The Handmaid's Tale" as the character Eden, a child bride. That same month, E! reported that Glen Powell and Nina Dobrev had decided to pump the brakes on their relationship. The reason? Well, Dobrev was apparently landing so many acting gigs that she simply didn't have time for a relationship. "They haven't been spending much time together since the end of the summer," a source explained. Another insider dished, "They are still seeing each other, but have cooled things off a little because of busy schedules." Speaking of things that are cool (or ice cold, rather), Powell had enough time available in his schedule to jet off to Antarctica in December 2017. 

Dobrev and Powell's sorta-split was reportedly amicable, but it eventually stuck. By December 2018, Dobrev had found a new leading man in director-screenwriter Grant Mellon. Her next serious relationship was with Olympic snowboarder Shaun White, and in May 2022, Us Weekly reported that the couple decided to walk their first red carpet together at the premiere of Powell's movie "Top Gun: Maverick." The outlet noted that Dobrev was close pals with Powell's co-star Miles Teller, so she wasn't necessarily there to celebrate her ex's big career achievement (or to try to make him feel awkward).

Aside from her career as an entertainment reporter and television host, Renee Bargh's biggest claim to fame might be getting a cheeky wink from Brad Pitt during a 2020 Extra interview — while she slyly humble-bragged about being romantically linked to the actor. But when Us Weekly reported that she was dating Glen Powell in November 2018, Bargh kept her lips zipped. A source, however, was willing to talk, telling the tabloid that the pair had been dating for half a year and were already sharing Powell's abode. Bargh also reportedly attended Powell's 30th birthday bash. The rumored couple celebrated with stars including Rachel Bilson, John Stamos, Lena Waithe, Chord Overstreet — and Powell's ex, Nina Dobrev. Dobrev even mentioned the party on Instagram, giving a celebratory snapshot with a caption that read, "Glen hit 30 before me and this is how I feel about it."

By November 2019, Bargh was telling the Daily Mail that she was single and hoping to find love with a fellow Aussie. A month prior, Powell had told Glamour that he was unattached as well. "I don't like cheese. It's cost me a lot of friendships ... It's been sort of a nightmare. Maybe the whole cheese thing is why I'm single," he mused. Sydney Sweeney, meanwhile, told Story & Rain that she is an avid appreciator of the dairy product, particularly when it's served on a platter with various meats, FYI.

After making waves with her roles in "Euphoria" and "The Handmaid's Tale," in 2020, Sydney Sweeney signed on to appear in the HBO series "The White Lotus." Her entitled character, Olivia, was Regina George on steroids — imagine if the mean girl read Nietzsche and wielded wokeness like a weapon. Olivia also came from a family that was wealthy enough to vacation at an exclusive resort, which is something Sweeney told British GQ that she'd never done before. 

While filming "The White Lotus" at the Four Seasons in Maui, Sweeney and her castmates enjoyed an experience like no other. Lockdown was in effect, so everyone working on the show didn't have to share the luxurious facilities with any guests. "It felt like a tropical version of 'The Shining,'" Sweeney told TVInsider. "We were stuck there, but it was a beautiful kind of stuck." At first, no guests were allowed to visit, but once everything started opening back up again, Sweeney's boyfriend jetted off to the islands and helped her turn her pandemic work trip into a romantic holiday. In November 2020, Just Jared published photos of Sweeney and Jonathan Davino sunbathing on a beach in Maui and frolicking in the ocean, where Davino held Sweeney up as she wrapped her legs around him. They were also photographed digging in the sand and gazing adoringly at each other. The rare pics of the super-secretive pair's PDA provided proof that they were still going strong.

After Sydney Sweeney got engaged to Jonathan Davino, she indicated that she was plotting a course for her future as a wife and mom. But in an interview with The Hollywood Reporter, she confessed to having some reservations about following her desired family plan. "I want to have a family, I've always wanted to be a young mom," she said, "and I'm worried about how this industry puts stigmas on young women who have children and looks at them in a different light."

How motherhood might affect her career wasn't Sweeney's only concern at the time; she was also afraid of being financially insecure. It was a topic she discussed with her "Sharp Objects" co-star Amy Adams back when they worked together. "I was worried that, if I don't work, there is no money and no support for kids I would have," Sweeney explained. She revealed that she was taking on as many acting projects as she could handle and accepting paid partnerships with brands to ensure that she could support herself — and pay everyone she employs to ensure that work keeps coming her way. "I don't have anyone I can turn to, to pay my bills or call for help," she said. So what of Davino? Well, TMZ reported that his family runs the cannabis packaging business Final Bell and the vaporization hardware company 14th Round, but it's unclear what this means for the size of his own bank account.

Is it possible for romantic leads to be too believable? As soon as set photos from the filming of "Anyone But You" started making the rounds on social media, netizens immediately noticed Glen Powell and Sydney Sweeney's scorching-hot chemistry. One Twitter user shared snapshots that showed the actors laughing and embracing, claiming that the interactions happened between takes. "Yep something's brewing over there," they wrote.

Then, in late April 2023, a video of Powell dipping Sweeney backward on a couch went viral on social media. Sweeney was smiling serenely with her eyes closed, and Powell was laughing as he looked down at her. "Rom-com actors exhibiting cheating behavior," read one response to the video. "Hollywood is back." Per Page Six, Gigi Paris unfollowed Sweeney's Instagram page after the PDA began raising eyebrows, a seeming indication that she did not approve of the co-stars' flirty behavior. But it didn't stop.

During CinemaCon, fans learned that Sweeney had given Powell a nickname. "We love seeing ourselves on the big screen," Powell quipped, to which Sweeney teasingly responded, "Oh, please, Top Gun." Her co-lead then informed the crowd, "I love when she calls me that," per People. The official Sony TikTok account also shared a video of the pair describing their "perfect date." Sweeney gazed up at Powell while imagining her ideal romantic outing and started giggling profusely when he recalled a rugby team reacting to Sweeney as if they were on "The Bachelorette."

Rapt netizens following the saga of Sydney Sweeney and Glen Powell as if it were a soap opera likely thought that their suspicions were confirmed on April 28, 2023. That day, photos of Jonathan Davino leaving Sydney Sweeney's house with luggage and the couple's dog caught the attention of TikTok detectives. But the following day, the Daily Mail published pictures of Sweeney and Davino walking side-by-side — while wearing matching black ensembles, no less — during an outing in NYC. The publication made sure to note that Sweeney wasn't wearing her engagement ring.

TMZ spoke to Jeetendr Sehdev, an expert on celeb branding, and he suggested that Sydney and Powell's flirtatious off-screen behavior was just an act to drum up buzz for their movie. He argued that they needed the attention because their names alone weren't enough to entice viewers to watch it.

Interestingly, Sweeney once expressed concern that her work alone wouldn't be enough to keep her career afloat. She was talking to Elite Daily about the attention Pete Davidson gets because of his love life. "If you have that one big moment, people are like, 'Oh my god,' and you become something," she said during the 2019 interview. "Sometimes I'm worried that because I'm not crazy or I don't do anything, that I'm just going to trail off." Well, maybe she finally got that moment that made her something more than a talented actor with a double Emmy nomination.