I always loved traveling, from my first trip to Italy as a 14 or 15 year old. My love for points and miles really kicked in in college. I was living in Massachusetts, and my girlfriend was living in Battle Creek at home for the summer.
I discovered I could make more of a living being bumped off two different airline's flights every single Friday from Detroit to Boston than I could at the work study and part time job I had at the time, and I was hooked, I literally made my living for two summers being bumped off the same group of flights every Friday.
When the frequent flyer programs started coming along and hotel points and the rest it was a total no brainer to join them. I was lucky in that I had moved on to a job that required travel to totally unknown places to me until the day before I was called to go for two or three weeks at a time. It just made sense to collect whatever benefits I could from it and use the free trips as often as I could.
My wife, who lots of people here have met, was never overly into it (obviously before you guys met her). One day we were staying in the Waldrof in New York, I had to work late that night and it was the cheapest room in the Hilton chain in the city, and it was a blizzard.
She checked in hours before I got there, and all I remember is her and a friend calling me to tell me about the massive suite they upgraded her to. It was obviously reserved for somebody else (the name on the card with the chocolate covered strawberries and bottle of wine) who couldn't make it because of the storm.
She never ever complained about points or miles since then.
We have matured in the collection of it all, hotel points don't mean that much at all to us anymore. Once the value of status dropped it opened an entire world of smaller bed and breakfasts, home rentals, cottages, boutique hotels, etc for our personal travel. If I need a night at an airport before a trip now I'll priceline it and save, in the case of this weekend for example, well over a hundred dollars for the night. That adds up pretty fast.
Airline status however still matters. Free bags, no lines, boarding first, etc and now that she travels on and off for work she goes for every mile she can.