I started playing wargames with my older brother when I was about 12 starting with Gettysburg and Tactics II. After that my family had no problem figuring out what to get me for Christmas and birthdays so the pile grew and grew...and grew and grew. I did play "family games" on occasion, though. Side story: one Christmas when we kids were about high school age, we opened the normally few gifts - at that point books and clothes and tools for dad. Then we just sat there staring at each other. After that there was a family "tradition" that the dog would buy us a board game every year.
When I went off to college, I took a few wargames along; but seldom found any gamers so played a lot of solitaire and PBM. Note #2: as a college junior I started PBM with a junior in high school way east in Maryland. We played and played and played for about 10 years then RL cut into that in the way of our respective careers; but to this day we still exchange cards at Christmas. It's been 44 years now and we've yet to meet face-to-face!
After college, when there was a little extra money coming in I started getting Strategy & Tactics, then The Wargamer and Command, all magazines that came with mostly wargames. I collected them until about the mid-'90s and even had a couple of short articles published in Command magazine. Along about 2006 I stumbled onto BGG and since then have been learning one aspect of the hobby after another. Since retiring from the working world for health reasons, BGG has given me a large boost in "sanity" by giving me something to do. For that I owe you all my thanks.