#4: Layla Roberts: The Beginning (Late 1990s)

Before Tom Brady became a household name in the NFL, he was briefly linked to model and actress Layla Roberts in the late 1990s. Roberts, a former Playboy Playmate, was known for her stunning looks and past relationships with celebrities.

While little is known about the exact details of their romance, reports suggest they had a short-lived fling before Brady’s rise to superstardom. At the time, Brady was still a college football player at the University of Michigan, making their connection an interesting but fleeting.