In honour of Jensen's birthday, I decided to do a This Day in Supernatual-Universe History for March 1st. I've done this for Jared's birthday before, but not Jensen's. As usual, I follow chronological time rather than the "soap-opera" time that the show uses, and everything is taken from my timeline.
A further note: I haven't actually timelined the last two episodes yet, so my guess for 2015 might prove to be inaccurate.
2006 - Sam and Dean talk to Sam's college friend Rebecca after she sends Sam an email telling him that her brother (and Sam's friend) has been falsely arrested for a crime he didn't commit. (Some things never change, I guess.)
2007 - Dean's happy to discover a werewolf hunt, until Sam falls in love with it.
2008 - Sam and Dean nurse their wounds after helping the Ghostfacers hunt a leap-year ghost at the Morten house. They're waiting to see the final edit of the Ghostfacer's show and Dean has probably already started assembling everything he needs to make a device capable of destroying the footage.
2009 - Dean Smith and Sam Wesson both start new jobs at Sandover Bridge and Iron Inc.
2010 - The dead have risen in Sioux Falls, South Dakota - but there's a reason Bobby hasn't called Sam or Dean about it.
2011 - Dean is working construction and living with Lisa and Ben Braeden. Elsewhere, Sam is hunting without a soul.
2012 - Sam and Dean might be in a parallel universe - only, no one wished Dean a happy birthday, so maybe not... probably that's already happened, and on March 1st the boys are busy fixing Bobby's bay window.
2013 - When Sam tries to prevent another hunter's kid from experiencing the grief of losing her father, Dean has to come to the rescue. Bobby has been dead for close to 5 weeks.
2014 - Dean may have found Castiel in Purgatory by now, and he may be traveling with Castiel and Benny to try to find the way out. Sam is working as a handyman at a motel, while dating a local veterinarian named Amelia.
2015 - Sam and Dean might be hanging around their new home in the Men of Letters bunker doing research and waiting to hear from Kevin about the next trial. Sam might be coughing up blood occasionally and they haven't heard from Cas in at least a month, but other than that, things are good.