My very first frequent-flier card was Southwest. Late 1980's...we'd buy the $19 MCI-MDW fares to go see the Cubs. It was a physical card where they logged flights, IIRC.

My next one was AA. I was in college in the UK...on one of my flights back to MCI a flight attendant walked through the cabin with cards to fill out to join. I did so and was thrilled when, after a couple of round trips, I had enough for a free flight.

I'm nearly 100% positive I blew those first 25k AA on something ridiculous like MCI-ORD-MCI. :o

Then, after graduation, I got a consulting project in Chicago and quickly reached Plat on the short segments to/from ORD. I also began meeting other business travelers and learned key insider tips like "Stop blowing your miles on $100 flights!" @:-) This was the late 90's...an excellent era for cheap Europe fares and 25,000-mile upgrades on any fare with no copays. ^

My first hotel program was Marriott Marquis, also from the mid-90's or so. I had a small number of stays but was impressed at the value and how usable the points were. (To this day, I remain mostly impressed with Marriott Rewards' value and usability.) I joined HHonors at the Hampton Inn in Stephensville, Michigan during the Christmas Eve Blizzard of 2000*. I joined SPG after joining Flyertalk and reading about the Amex and only really began staying at Starwood hotels as a result of that.

*Note to Avis: when/if global warming ever fully melts the snow from that godforsaken blizzard, you'll find your broken-down Dodge Neon in the parking lot of the Paw Paw Big Boy restaurant.

My big hit and subsequent addiction to FF programs was in the early 80's. I was a student at UM (Miami) and Eastern Airlines had a promo running with the football program where you could get 5K miles for every season ticket purchased...they had a deal for like $99 for a family pass plan and I bought 100 of them...I then gave some away to Boy's Clubs and re-sold the majority of them...I still remember the day when my statement showed up and I had 500K. They also made me EP...free upgrades, which I used on a MR to Lima for $99. I still remember the caviar cart coming thru the aisle...

When Continental opened up new service from Phoenix to Las Vegas in the late 70's, I'd guess 78 or 79, they offered a "Fly for Chickenfeed" promo. Either bring a pound of chickenfeed, or 25 cents for a roundtrip ticket. Limited to whatever empty seats they had.

I talked my mom into it, although I think I actually had to clean my room. Went to the old original terminal in Phoenix pretty early to wait in line. It was pretty fun, and at one point I was given someone's ticket that was ahead of us, which since I needed two, I sold to someone for $5.

In the end, made it on the plane later at night. Quite a fun experience, and my first jet airplane, where I made money on the flight. :)

I started when I planned two back to back study abroad programs in Rome and Tokyo with a stop in India. The RTW was a perfect for such a plan and once while discussing this package with a UA agent, she suggested I look into creating an account. Since I booked it with UA, I opened a UA FFP without any analysis of whether it might be the best for me, luckily it did till I discovered starnet. Ever since I have been hooked.

Started in college for me. Loved finding ways to get stuff for free! I have done dumpster diving for Wendy's Air Tran Cups, I have spent 24 hours at a walmart to buy a PS3 and ebay it.

Just love the freebies!

For me, it's all about doing it to the extent possible. I see it as a challenge. There's a higher tier than the one I'm at? Alright, let me see if I can get there...