While his ex-wife, Gisele Bündchen, moved on with her jiu-jitsu instructor, Joaquim Valente, Tom Brady hasn’t been in a serious relationship since the divorce. He’s been linked to several women in the time since, including Irina Shayk and Isabella Settanni, but those rumors never amounted to anything substantial. Once again, it seems Brady’s only true love remains football.
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Now, fresh reports are linking him to another high-profile name: actress Sydney Sweeney. Speculation began after the two were spotted looking quite friendly at Jeff Bezos and Lauren Sánchez’s lavish wedding.
Witnesses claimed they were spotted chatting at the bar, dancing together, and sharing what appeared to be a heartfelt conversation. So, are they dating? Is this the beginning of something more? Caroline Hendershot doesn’t think so.
On a recent episode of Well Played, she explained that people are naturally drawn to someone like Sweeney—not just because of her beauty, but also her immense popularity. According to Caroline, Brady was simply enjoying himself at the party, dancing and mingling with several guests, Sydney Sweeney included. She emphasized that there was nothing particularly romantic about it.
” If I myself, Caroline Hendershot, was talking to someone as beautiful as Sydney Sweeney or Sydney Sweeney herself, I too would try to spend a significant amount of time with her. Maybe in turn it would make me cooler. Ideally, that’s where the brain would go. But I also heard from another source that he (Tom Brady) was dancing with everyone, not just her. Apparently, he was dancing with Brooks Nader, who I think was on Dancing with the Stars.”
While that might be true for most, Brady is already the GOAT—his fame doesn’t need a boost. Still, she implied it might have happened subconsciously. Her co-host, Blake, even raised a cheeky but valid question: “Do we think Tom Brady can flirt?”
Caroline believes he can—but she also doesn’t see him as a smooth-talking, effortlessly charming ladies’ man. In her view, much of Tom’s identity and the energy he brings to interactions is shaped by his past as a professional athlete. His job did most of the talking for him. Being Tom Brady, the football icon, was the main draw—that’s what built his aura.
But Blake made an important point: Brady is no longer an active NFL player. The game no longer defines him the way it once did. Without football as a backdrop, people are left wondering who the real Tom Brady is.
“He is not one anymore. This is important because you leave the game, you mourn the game, you mourn the life you had. Now what? What is your personality? What is his personality these days?”
And that’s where things got even more entertaining. Blake bluntly called Brady “rizzless”—as in, lacking the charm or game to flirt effectively. Why? He suggested it might have something to do with Tom’s rumored cosmetic procedures—particularly the fat removal from his face—which, according to Blake, has left him looking like a mannequin with barely any facial expressions. A silver tongue? Maybe not. A frozen face? Possibly.
“To me, he is like rizzless. I don’t know why? It might have to do with the buccle fat removal. I have to say it’s all in the face.”
So, despite all the buzz, there might be nothing going on between Tom Brady and Sydney Sweeney. Both parties have declined to comment, which has only fueled speculation—but for now, it seems to be just that: speculation.
Even if there was something, the 20-year age gap would certainly raise some eyebrows. It almost feels like Brady is either trying to compete with Bill Belichick—who’s reportedly dating Jordon Hudson, who is nearly 50 years younger than him—or channeling his inner Leonardo DiCaprio, clinging to youth by dating much younger women.
