I am 45, so 1986 was my first.
Now, Buckner did not crush me - I fell asleep. I was 8. My dad said he'd let me know what happened if I passed out. Famous last words. But I was crushed by Game 7, where the Sox had a 3 run lead! That is what is wild sometimes. Like in 1975, the Reds lose one of the all time stomach punch games and still won the next road game.
I was in business school in 2003. We had a happy hour on the Thursday night, and me and a few buds went. They had Game 7 on the big screen. I was the only Red Sox fan in the group - but Yankees losing can unite lots of neutral fans. I was going to drive somebody home afterwards - but when Boone's homerun went over the fence, Todd (the guy I had to drive) looked at my face and said "I'll figure out how to get home." I nodded, "Thanks". I went home and stared. My mom called saying "I'm so sorry". I've never had my car stolen, but I felt what I imagine how someone feels walking up and down past the empty parking spot where the car was taken from. It was also the first time I felt like I was going to be another one of those "Sully from Revee-ah" guys who never saw his Sox win it all.
Of course 2004 happens - and indeed the way it happened was such that I am almost grateful for 2003 as its place in the two year dramatic arc. The other titles are great - I am certainly not going to pooh pooh them ... but no team's fan base anywhere (short of something like Leicester City winning the Premier League) will have as sweet a championship as 2004. All of the circumstances together are nearly impossible to find.
That said, if Texas wins it all - I will be happy for them. They were on the losing end of either the greatest (or IMO 2nd greatest) game of this century - one of the real stomach punch losses in baseball history - so it would be nice for their fans. And of course, I am happy for Nate. It is also worth remembering that Texas is doing this after losing their ace after just 6 starts this season.