Tom Brady, the retired NFL legend, found himself in a hilarious and awkward situation during a recent interview with Caleb Pressley on the Sundae Conversation. The 47-year-old quarterback was questioned about his former coach, Bill Belichick, and his much younger girlfriend, Jordon Hudson. The humor arose when Pressley asked Brady, “If Bill Belichick’s girlfriend needed it, would you rent a car for her?” This playful jab referenced the fact that most car rental companies require drivers to be at least 25 years old to avoid the “Young Rental Fee.” Brady, clearly caught off guard by the question, burst into laughter and struggled to compose himself before finally responding, “I don’t want any liability.” His reaction not only highlighted the absurdity of the situation but also showcased the lighthearted dynamic between Brady and Pressley.
The interview also delved into Brady’s thoughts on Belichick’s personal life and habits. When asked if Belichick followed his stringent TB12 method, which emphasizes a strict diet and exercise routine, Brady responded, “Nah, he’s a big carb guy.” This playful jab at Belichick’s eating habits added another layer of humor to the conversation. Pressley further probed, jokingly asking if Belichick’s girlfriend, Jordon Hudson, adhered to Brady’s health regimen. Brady’s succinct reply, “Sounds like it,” suggested that Hudson might indeed be following a healthy lifestyle, given her youthful and vibrant appearance. The exchange not only poked fun at Belichick’s tendencies but also subtly highlighted the significant age gap between him and his 24-year-old partner.
Speaking of Belichick and Hudson’s relationship, the couple has been making headlines since they reportedly started dating in 2022. The two met on an airplane a year prior and exchanged contact information, which marked the beginning of their romance. Their relationship came to light shortly after Belichick ended his 16-year relationship with his ex-girlfriend, Linda Holliday. Despite the 48-year age difference, insiders have revealed that Belichick “couldn’t care less” about the gap, as he deeply appreciates Hudson for who she is. A source close to the couple even described Hudson as an “old soul,” suggesting that the two share a deep emotional connection that transcends their age difference. “Age is just a number to them,” the insider added, emphasizing that their bond is rooted in mutual respect and understanding.
Over the past year, Belichick and Hudson have gradually become more public with their relationship. They began sharing photos of their vacations and holidays on social media, giving fans a glimpse into their personal lives. In December, the couple took a significant step by making their red carpet debut at The Museum Gala in New York City. The event, held at the American Museum of Natural History, marked one of their most high-profile appearances together. Just recently, the pair attended Super Bowl 2025 in New Orleans, further solidifying their status as a committed couple. Their growing comfort with public attention suggests that they are becoming more confident in showcasing their relationship to the world.
Brady’s interview also shed light on his own relationship with Belichick, a man he worked with for many years during his time with the New England Patriots. While Brady’s comments about Belichick’s eating habits were lighthearted, they also hinted at the differences between the two legendary figures. Brady, known for his disciplined approach to health and fitness, seems to have a playful understanding of Belichick’s more laid-back lifestyle. At the same time, Brady’s refusal to get drawn into discussions about Belichick’s personal life, as seen in his humorous response about the car rental question, reflects a deep respect for his former coach’s privacy.
In the end, the conversation between Brady and Pressley served as a reminder of the unique dynamics at play in the world of sports celebrities. From the humor surrounding Belichick’s relationship with Jordon Hudson to Brady’s own insights into his former coach’s habits, the interview offered a mix of laughs and personal anecdotes. It also highlighted the resilience of Belichick and Hudson’s relationship, which continues to thrive despite the significant age gap and public scrutiny. As the two navigate their life together, they seem determined to focus on what truly matters—the connection they share—and let the rest of the world fade into the background.
