Tara Reid
When Tom Brady was in the very early stages of his football career, he teamed up with Tara Reid.
"We’d just see each other on and off," the American Pie actress recalled to Bustle in 2023, noting she and the quarterback briefly dated in the early aughts before her engagement and split from Carson Daly. "It was nothing serious, but it was fun. We’d go to beer places and have fun and dance. He was cool."
And if you want the play-by-play on how they met, Tara revealed they crossed paths at the ESPY Awards.
"We just started talking and hanging out," she shared with NBC Sports Boston in 2022, "exchanged phone numbers."
She also didn't call foul on Tom's smooching skills, adding he's a "great kisser."
Bridget Moynahan
By the time Tom won his first Super Bowl with the New England Patriots in 2004, he'd entered a new relationship with Bridget Moynahan.
And as the Blue Bloods star and the athlete posed for photos at glamorous events like the Met Gala and Oscar parties, they seemed like the picture-perfect couple.
"I can be myself around her, and there's not many people I can be myself around," Tom said in a 2005 60 Minutes interview. "It's fun to be around your best friends who know you well, and she's someone that I consider one of my very best friends."
Not long after, Tom met Gisele Bündchen. And as their relationship was beginning, he learned that Bridget was pregnant with his child—leading to a media frenzy.
"I would have cars following me, and men hiding in the bushes outside my house," she recalled to People in 2019. "As a new mother, you want to just protect your child. That kind of attention felt like a threat."
Bridget gave birth to son John Edward Thomas Moynahan (a.k.a. Jack) in August 2007. And over time, she, Tom and Gisele formed a solid co-parenting bond.
"Tom and I made a decision to raise a child together and we both found partners that not only supported us in raising that child, but also loved our child as if he was their own," the actress, who wed Andrew Frankel in 2015, added. "I don't think you can ask for more than that. My son is surrounded by love."
Gisele Bündchen
After marrying in February 2009, Tom and Gisele added son Benjamin to their squad in December of that year followed by daughter Vivian three years later.
The supermodel took a step back from the runway to focus on raising their family, and she and the kids were in the stands cheering on the QB as he racked up a total of seven Super Bowl wins.
But in 2022, rumors spread that it was game over for the power couple. And in October of that year, they divorced.
However, Gisele slammed speculation the breakup was caused by Tom reversing his decision to retire and play for the Tampa Bay Buccaneers one more season before ultimately hanging up his cleats for good in 2023. Instead, she noted they simply grew apart.
"What’s been said is one piece of a much bigger puzzle," the fashion icon told Vanity Fair in 2023. "It’s not so black and white."
Pledging to not let their divorce fumble their co-parenting relationship, Gisele and Tom moved on. And in early 2025, she welcomed a baby with boyfriend Joaquim Valente.
Reese Witherspoon
By the spring of 2023, Tom was already intercepting rumors about his love life. The gossip included reports he was dating Reese Witherspoon, who had recently split from her husband Jim Toth.
However, a rep for the Legally Blonde objected to the speculation and made it clear it was completely false.
Kim Kardashian
And if you were keeping up, then you might have also seen rumors that Tom was dating Kim Kardashian. But in May 2023, a source confirmed to E! News that while the two have friends and business partners in common, they're not dating.
Kim even laughed off the rumors during Netflix's The Roast of Tom Brady.
"I wasn't going to come tonight, but since I'm not here as Tom's date, there's still a good chance I might, " the reality star joked during the 2024 comedy special. "Speaking of Tom and I dating, I know there were some rumors that we were. And I'd never say if we did or not—I'd just release the tape."
Irina Shayk
Still, there was no timeout in the dating speculation and Tom was linked to Irina Shayk after they were spotted together in L.A. in the summer of 2023.
However, the romance rumors didn't have a long runway as reports spread that fall that the model and the MVP had already parted ways. Although, they were photographed together again that December.
Sofía Vergara
The "are they dating?" questions kicked off again in July 2025 when Sofía Vergara posted several pics from a star-studded gathering aboard a yacht, including one of her and Tom sitting at a table with J Balvin nearby.
But when the Daily Mail, citing a source, reported the Super Bowl champ was planning on staying single and that the Modern Family star was "too old" for him, his rep fired back.
"Tom never said, nor would he ever say, anything like this," the rep told People July 10. "It is pure fiction."