Tony Stewart's girlfriend in 2003 was Jamie Schaffer. Schaffer was a calendar model and dated Tony Stewart from 2002 to 2004. The couple separated because of Tony Stewart's anger-management problem.
Before Jamie Schaffer, Stewart was briefly engaged to Krista Dwyer. He also dated Tara Roquemore between 2006 and 2008, and appeared with her publicly at the NASCAR Martinsville Cup race. Stewart is currently single, lives in Columbia, Indiana and has no children. He is the only racecar driver to win a championship in the IndyCar and NASCAR. Stewart has amassed a net worth of over $70 million due to his 18-year racing career.