Tom Brady and Bridget Moynahan's relationship had its fair share of ups and downs. When the pair were first linked in early 2004, they were both experiencing career highs. Brady had just won his second Super Bowl as quarterback for the New England Patriots, while Moynahan had famously appeared on Sex and the City and starred in films including Coyote Ugly, Serendipity and The Recruit
In 2002, Brady briefly dated to model Layla Roberts, who was named the Playmate of the Month in October 1997
Tara Reid Brady was also rumored to have been involved with Tara Reid in 2002. When asked about their alleged romance, the "American Pie" star claimed she had kissed the athlete
T The actress, who has appeared in "Sex and the City," "I, Robot" and "Blue Bloods," dated the then-Patriots quarterback from 2004 until December 2006.