New Hollywood Threesome? Newly Single Sydney Sweeney, Orlando Bloom, And Tom Brady Hang Out
By Kelly Coffey-Behrens on June 28, 2025 at 12:45 PM EDT

Talk about a star-studded surprise as Orlando Bloom, Sydney Sweeney, and Tom Brady were spotted together in Venice over the weekend, following their attendance at Jeff Bezos and Lauren Sanchez's star-studded wedding.
The trio’s unexpected outing has fans buzzing, especially with the recent drama surrounding their love lives.
From Orlando Bloom’s fresh breakup with Katy Perry to Sydney Sweeney’s split from fiancé Jonathan Davino, and Tom Brady’s off-and-on relationships since his 2022 divorce from Gisele Bündchen, this group has everyone wondering what’s really going on behind the scenes.
Tom Brady And Sydney Sweeney Spark Rumors After Dance And Chat At Jeff Bezos’ Wedding

TMZ, which also obtained the snaps, has learned that Tom and Sydney were spotted chatting it up at The Gritti Palace, where several wedding guests were staying.
It seems the two hit it off, as sources revealed they even shared a dance at the wedding on Friday night. While Tom certainly danced with others, it was his time spent with Sydney that caught the most attention.
"Tom Brady already has everything. If he gets Syd Sweeney he will become too powerful and may be our only chance of beating AI," one X user said after hearing the news.
Someone else claimed, "They kinda look cute together."
"LFG. Tom Brady is the GOAT," a third replied.
Another pointed out the age difference. "Sydney Sweeney is 27 years old. Tom Brady is 47 years old. It seems Brady is following Belichick's steps," they said, referring to Bill Belichick's 49-year age gap between him and his girlfriend, Jordon Hudson.
Orlando Bloom Enjoys Life After Split With Katy Perry

What makes this sighting even more significant is Orlando Bloom attending the wedding solo, without Katy Perry, following their recent split. Insiders say Orlando was ready to enjoy the celebration, and who could blame him?
Seeing the "Pirates of the Caribbean" star spending time with Sydney Sweeney clearly shows he's embracing life post-split and having a good time.
"Orlando Bloom wins again," one X user said. "What a good swap."
Others simply praised how wonderful a person Sweeney is, saying, "Who wouldn't chat her up given the chance?"
It's worth noting, however, that Sydney Sweeney, Tom Brady, and Orlando Bloom weren't alone during their Venice stroll. They were accompanied by a group, which suggests they could simply have been hanging out as friends with no romantic connection.
Sweeney Embraces The Single Life After Split From Fiancé Jonathan Davino

Meanwhile, Sydney Sweeney, who recently ended her engagement with Jonathan Davino earlier this year, has been living her best life post-breakup.
As many know, Sweeney and Davino were together for several years after first being linked in 2018, with their relationship growing steadily before getting engaged in 2022.
Ever since her split from Davino, she has been seen with several Hollywood heartthrobs, including her "Anyone But You" costar Glen Powell, as well as newly single Machine Gun Kelly.
Tom Brady's Post-Divorce Love Life

And Tom, of course, has been keeping things casual with a few flings since his divorce from Gisele.
The now-retired NFL quarterback was briefly linked to Reese Witherspoon, though those rumors were shut down solely based on the fact that she had never met the quarterback. Additionally, rumors about a potential romance with Kim Kardashian began circulating in March 2023, though representatives for Brady firmly denied any romantic involvement.
Then, in July 2023, Tom Brady was spotted getting close to model Irina Shayk, sparking rumors of a new romance. A source told PEOPLE at the time that the two had "been in touch for a few weeks" and that there was definitely "a spark" between the retired NFL star and the Russian model.
However, rumors suggest things ended for good in 2024.
Is There More To Orlando Bloom, Tom Brady, And Sydney Sweeney’s Venice Outing?

While this Venice outing might seem innocent enough, the timing has everyone wondering if there’s more to this trio’s connection than meets the eye.
With Orlando Bloom navigating life after Katy Perry, Tom Brady keeping his options open, and Sydney Sweeney stepping out of a serious relationship, the possibilities are endless. Was this just a friendly get-together, or could it be the start of something more? Only time will tell.