At What Point?

In about a month I will be almost face-to-face with 2010 eve. Am I missing something about my 20s???? At what point does the 'magical lifestyle' kick in?

-At what point do you get to ring in the new year at a fab party filled with your fav 20&30somethings in the sexiest of sexy attire you can find?
-At what point does the magical surprise Valentine's Day trip happen, where you're whisked away with nothing more than a wrap cap and pedicure? And/Or at what point do you spend Vday @ NY Fashion week?
-At what point do you use Memorial Day weekend as a way to really kick off the summer? (instead of just sleeping in)
-At what point is the concept of 'summer vacation' a fluid concept that happens year round?
-At what point do you spend July 4th in D.C. or Boston or if you're sense of irony is high, spend it in London?
-At what point do you get to go to Europe without having to have a year-long payment structure?
-At what point does Labor Day mean Caribbean vacation?
-At what point can you leave your passport on your dresser because you'll just have to use it again sooner than later?
-At what point does winter mean Pocanos?
-At what point do you and your friends either own your own business (and so PTO isn't an issue) or have so much PTO that all of this travel is not only feasible, it's encouraged?
-At what point do you spend the next new Yrs at home having a small dinner party, because you've done everything you wanted to do all year long?