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During the 1990s, Judd dated baseball player Brady Anderson, singers Lyle Lovett and Michael Bolton, and actors Matthew McConaughey and Robert De Niro. She became engaged to Scottish CART, later IndyCar driver, Dario Franchitti, in December 1999, and the two were married at Skibo Castle, near Dornoch, Scotland, on December 12, 2001. She and her husband divide their time between a home in Scotland and their farm outside Franklin, Tennessee. Judd can be easily be recognized in Gasoline Alley in her white hat almost every year, and was present at the 2007 Indianapolis 500 when her husband won the race.