Lookingland graduated from
Loyola Blakefield. He attended
Bucknell University, playing on the men's soccer team from 2001 to 2004. He was a 2004 Third Team All American. In 2003 and 2004, he played for the
Chesapeake Dragons of the
Premier Development League during the collegiate off season. On 4 February 2005,
Real Salt Lake selected Lookingland in the second round (thirteenth overall) of the
2005 MLS Supplemental Draft. He spent two seasons in Salt Lake. In 2007, he moved to the
Harrisburg City Islanders of the
USL Second Division. In 2008, he played for
Crystal Palace Baltimore. In addition to his outdoor career, Lookingland has an extensive indoor career. In 2005, he signed with the
Baltimore Blast. He was named to the 2005–2006 All Rookie team and was the 2012
Major Indoor Soccer League Defender of the Year. ==Coach==