Blake&Penn By AncaEmily Period: Jan 1, 1998 to Dec 31, 2012 ... Jun 15, 1998 Blake and Penn meet for the first time. May 10, 2007 Blake and Penn meet again Jul 22, 2007 Blake&Penn getting much closer after shooting the Pilot Aug 17, 2007 First Kiss as Dan and Serena Oct 8, 2007 Penn&Blake get together Oct 30, 2007 Blake&Penn have Sex for the first time May 21, 2008 Vacation in Mexico Sep 29, 2010 Blake&Penn break up