It really is surprising how much air travel has changed during my lifetime. I remember feeling like kind of a loser in (public) high school back in the 90s when a select few kids would return from some exotic location for the winter break. But the consolation was that at least, like me, none of my friends went anywhere. There was one kid in my friend group who had flown once before. But if I recall correctly, it was to visit a divorced parent or something, so even though flying struck all of us as a crazy and aspirational way to travel, we all still felt bad for him.

By the time I was in my 20s (in the early 2000s), the situation was totally different. The most ridiculous: sometime in 2009, JetBlue had a deal, announced on radio, that you could purchase unlimited flights for 3 months for only $500. As my fiancee had moved to the western US for her medical school residency program, this was a godsend. I visited her every weekend... I don't remember if I took a full 12 trips, but it was more than 10. I would leave Boston immediately after work on Friday and then take a redeye and arrive back in Boston at 7am on a Monday. I haven't seen a deal like that in a long time, and flying has increasingly gotten worse since that experience, but it still is relatively affordable compared to my high school years.