2006 - Sam and Dean are in Richardson, Texas, investigating the Hell House and pranking each other. They meet two amateur ghost hunters named Ed and Harry, and are not impressed.
2007 - Dean gets a surprise when he goes to visit his old fling, Lisa Braedon, and discovers that she has a kid. Although Dean wants to stay, he knows that he can't - he's hasn't got much time left anyway.
2008 - Dean is being tortured in Hell. Sam is drunk.
2009 - Dean is hunting on his own. Sam is working at a bar in Garber, OK.