OK, I'll play. I'm OLD! and my memory is not so great, so an exact age or date is not going to be possible. But I've been playing various card games for as long as I can remember. Definitely before I had any actual money of my own. My Dad enjoyed gambling and cards and he taught me various card games as soon as I was able to hold them in my hands. I also played rummy games with my mom and my sister that was 10 years older than me. I seem to remember winning and losing pennies when we played. Then my sister got married when I was 10 and her husband also loved card games. Around then we started playing a game called pitch, which if I'm remembering correctly, did have a small monetary portion to the scoring. Nickels and dimes if I recall correctly. As a young teen, I earned cash delivering papers and odd jobs, so that's probably the first time my own money was at risk.
I don't remember exactly when I started playing poker, but my dad was in a regular poker group that did occasionally meet at our home. My first recollection of that was in high school. I would sometimes watch them play, but I never joined in, and we never played poker as a family back then. I did have a group of friends that would get together to play games, and sometimes we would play poker. I doubt that it was for more than a few dollars at a time. Probably no more than $5. This was in the 1970s.
After college, I moved away to Texas, and made friends with some people I worked with. One of them (don't even remember his name any more) hosted poker games every once in a while. There were no chips. We played with coins and currency. This was before Texas hold'em blew up and we played dealer's choice. Mostly draw and stud. To this day, I don't really care for those games, so that's probably why I don't remember it very well. I probably only played a few times before losing interest.
It wasn't until Hold'em became popular that I began to get really interested in poker. I think it was the early 2000s when I started playing free online NLHE with play money. About that same time I started buying some inexpensive plastic solid color diamond mold chips from a local gift store. Eventually I accumulated about 6-700 of them in probably 7-8 different colors, and I would use them to play family tournaments. Still very low stakes. Probably $5-10 buy ins. That was about it until I joined PCF in April of 2020. Once I got here, poker exploded for me, and became a huge part of my life.
