I hope 2017 goes better, collectively, than 2016.
Let's make ourselves feel a little better about our own lives by looking at what Sam and Dean have had to put up with over the years! I'm going to date everything January 1st of the new year, just so that it's not confusing, hopefully.
(Also, once again - I include the years that the show "skips")
New Year's Day in Supernatural
1955 - Mary Winchester is nearly 4 weeks old! Awww, so cute!
1959 - This is the first New Years that John rings in without his father, who has been missing for nearly 5 months now. John is 4 years old, but will be turning 5 sometime in the next 12 months.
1973 - John is serving in the Marine Corps during the Vietnam War. By now, he has been promoted to Corporal.
1974 - John and Mary celebrate the new year together, having overcome a trumultruous year in which Mary's parents both died very tragically.
1976 - Although John initially proposed back in 1973, this is John and Mary's first New Year as a married couple! I guess having your parents die really puts a damper on the wedding planning.
1979 - Mary is in her final month of pregnancy with her first child. :)
1983 - Mary is four months pergnant with her second child, who will, of course, turn out to be a little brother for Dean to play with. Dean is nearly 4 years old, and adorable.
1984 - John and the boys have their first New Year without Mary, who died only 2 months ago. Elsewhere in the world, Jessica Moore is only 24 days away from being born.
1990 - John hears about some suspicious sounding grave robbing in Windom, Minnosota, and decides to go check it out...
1991 - Adam Milligan is 3 months old. Aww, cute.
1992 - Sam enters this year with full knowledge of what his father actually does for a living and why they have to move around so much. No doubt, they have probably already left Broken Bow, Nebraska, after John accidentally missed celebrating Christmas with his boys and being there for Sam when he found out the truth.
1994 - Kevin Tran is a month old. So cute!
1995 - This will be the first New Years since Sam stopped believing in the Easter Bunny. :)
1996 - This is Ellen and Jo Harvelle's first New Year without Bill.
1999 - Lisa Braeden is 3-4 months pregnant after sleeping with a drifter who was NOT Dean.... or so she says. Also, Sam has had his first kiss by now.
2003 - Sam's first New Year at Stanford. And Dean and John's first New Year without Sam. If John hasn't been made aware of, and met, his third son Adam already, he will before September.
2005 - Sam has met and is now dating Jessica Moore. Dean has fallen in love with Cassie Robinson, but been rejected upon trying to tell her the truth about his life.
2006 - This is Sam's first New Year without Jessica, who has been dead for two months now. He has dropped out of school and is back traveling with Dean. We don't know exactly where they spend New Years, but we do know that Sam is probably feeling pretty good about saving his friend Zach from being charged with attempted murder. Dean, meanwhile, is legally dead and persumed to be a murderer, but that's okay with him. Next on the agenda is to continue to try to track down John.
2007 - This is Sam and Dean's first New Year, since John died roughly 4-5 months ago. The good news is that Dean's no longer keeping Dad's last words a secret from Sam - also, they successfully got Gordon arrested, so hopefully Sam's not going to become the target to any more hunters. The bad news is that they still don't know what's up with Sam's visions or what Dean has to save him from.
2008 - We never see it, but I'm sure this New Year celebration (or lack thereof) tears Sam up inside, becase he knows that unless he can save him, Dean will be dead before the year is over.
2009 - Dean is recovering in hospital after being severely beaten by Alaistair. Sam's confidence in his decision to use and embrace his demonic powers is no doubt growing, as he must feel pretty satisfied that even though he couldn't save Dean from the torture in Hell that he endured before angelic rescue, Sam could at least kill Dean's torturer when given the opportunity. This is Castiel's first New Year in the Winchester's lives. It's not the best start, given that he just uncovered a conspiracy of Lucifer-supporters in the ranks of his garrison, failed to protect Dean, an incured Sam's distrust and anger as a result.
2010 - We don't know exactly where the Winchesters were this New Year, but odds are, it was a sad affair, as they are morning the loss of Ellen and Jo Harvelle, and the discovery that their best weapon against Lucifer - the colt - is useless.
2011 - It is Dean's first New Year without Sam, who has locked in the cage with Lucifer for 7 months. He has Lisa and Ben Braeden there to support him during difficult moments though. Cas, meanwhile, tries to deal with the power vacuum left by Michael's absence in Heaven, and the growing threat of Raphael. Sam's body is off probably sleeping with some woman. Sam's soul is being tortured by Lucifer for the nth day in a row.
2012 - Dean no doubt has the best New Year in a really long time. It's true, he is no longer on good terms with Lisa, but he has Sam back! Yay! Sam, meanwhile, is entering the year confused as to the huge missing chunk of his memory, why Dean won't give him straight answers... unless Castiel has already told him, in which case, Sam is quietly disparing at how much guilt he could feel for actions done in an altered state that he doesn't remember.
2013 - Sam is so far handling the return of his memories pretty well, all things considered. He and Dean have made up from their latest fight, and things seem to be going not-bad, even though Castiel is dead and there are Leviathans everywhere. Dean is pretty messed up about Castiel betraying them, apologizing, and then dying. Also, he's stressed out about Sam's health... also there are leviathan trying to track them down and kill them. Dean spends a lot of his time drinking these days.
2014 - This is Sam's first New Year since Dean's death. (And Cas' death too). He has retired from Hunting, after aimlessly driving around the country for a few months first in a grief-stricken fugue, instead of trying to figure out what Crowley might have done with Kevin. Sam has a dog and Amelia Richardson, who recently lost her husband in the war, to support him during this difficult time. They most likely just get super drunk. Dean, meanwhile, spends the day with Cas and Benny, in purgatory, most likely unaware of what day or year it is on earth.
2015 - All things considered, this must be a pretty nice New Year for Sam, because he's got Dean back! Yay! Also Cas! Yay! Sure, their relationship is a bit strained, due to Dean having a pretty bad case of PTSD, but Sam's the pot calling the kettle black there, so he's not going to complain. Also, Cas is acting a bit weird since he inexplicably returned, but that's often the case, so it's probably nothing to worry about.
2016 - Sam and Dean's New Year is most likely a low-key affair. Kevin has only been dead a short time. Dean is back living at the Bunker, but the Winchesters are barely talking to one another. Dean also has a weird mark on his arm now, courtesy of Cain, that's supposed to help him kill Abaddon.
2017 - We don't know exactly where the boys are for this new year, but it's most likely after it has become clear that Dean cannot always control the murderous tendencies that the Mark causes. Sam is, no doubt, just thankful that Dean is alive, and is optimistic that they'll find a solution. He may have already found references to a Book of the Damned that might help, he may have already suggested that Charlie go check it out. In any case, I'd like to think that Sam enters 2017 cautiously optimistic, while Dean enters it cynical and dispairing. Cas, meanwhile, is just trying to figure out what the heck one does with the daughter of the man that you accidentally got killed, especially when you're still wearing his corpse. So awkward.
2018 - Again, we don't know exactly what the boys are doing this New Years, but odds are, that it's around the following time: Making up for past inabilities, Dean has successfully saved his brother from a cage with Lucifer in it. So, he must be feeling pretty good. Sam, meanwhile, is dealing with a lot of feelings and emotions after being in Lucifer's presence again, nearly 6 years after escaping him. Cas, meanwhile, has made a grave mistake, blamed, at least partially, on his problems with low self-worth. (I tell you, he and Dean are BFFs for a reason.)
2019 - Well, the world didn't end, so that's good! The show has given me absolutely no dates this far in S12. By my estimations, we're actually still in the summer and New Years hasn't happened yet.
And we're done!
May your 2017s be better than the Winchester's ;)