Matt Holliday and his wife, Leslee, married on December 30, 2000. They met on a blind date in 1999 in Stillwater during the baseball offseason when Matt had returned home from his first professional season following his selection by the Rockies in the MLB draft and Leslee was an undergraduate at OSU−Stillwater. Matt's best friend was dating a friend of Leslee's, and they wanted to do a double date, so her friend asked if she would go with Matt. The Hollidays currently reside in Stillwater, Oklahoma, and Jupiter, Florida, and have four children. They have three sons, Jackson (born December 4, 2003), Ethan (b. February 23, 2007), and Reed (b. July 24, 2013) and a daughter, Gracyn (b. November 7, 2009). They formerly resided in Austin, Texas, during the offseason until December 2010, following his signing of the contract with the Cardinals in January 2010. During the offseason, Holliday and his family have also lived in Stillwater, where he also has worked with his brother, Josh, on his swing. In the 2014−15 offseason, Holliday and his family moved to South Florida, allowing him to stay in optimal shape year-round, and his sons to continue to play sports in winter months.