~March 23/24, 2010-2011
(2006-2009 - we left off with Sam Wessen accidentally hitting on Dean Smith in an elevator)
2010 - It's around this time of year that Dean loses all faith in their ability to stop the apocalypse and he leaves Sam in an attempt to say yes to Michael. Sam, with the help of Castiel, finds him and stops him...through the power of love.
2011 - Dean is living with Lisa and Ben Braeden while working construction. He occasionally goes out for beer with his neighbour Sid, but does not talk about his past. Meanwhile, unbeknownst to Dean, Sam's body and brain is off Hunting with the Campbells.
Hope that was fun for you. I was suitably occupied for 10 minutes. I think I'll go out and do errands now.