Tom Brady dated actress Bridget Moynahan for almost three years, but after they pair broke up in December 2006, Moynahan discovered she was pregnant with their son, Jack. Brady was surprised to hear the news at the time. "Next thing you know, I found out that Bridget was pregnant with our son," he told Howard Stern in 2020. "So that was a very unique time ... and it challenged me in a lot of ways, again, to grow up in a different way," he said (as reported by People). In January 2007, Brady moved on with his now ex-wife, supermodel Gisele Bündchen. According to Bündchen, her connection with Brady was instant. "I knew right way—the first time I saw him," the supermodel told Vanity Fair when describing their first date.

While Brady was dating Bündchen, his ex, Moynahan, delivered Jack at St. John's Health Center in Santa Monica at 11:46 a.m. on August 22, 2007 (via the Boston Herald). Although InStyle reports that representatives of Moynahan stated that she and Brady "amicably ended their three-year relationship," Moynahan said she struggled to cope. "Going through that traumatic time of being heartbroken and then being pregnant turned my whole life upside down and inside out and just knocked the wind out of me," Moynahan told Harper's Bazaar back in 2008. "But now I have a child, and it's the best thing in the world," she added.