When I was 15 I put $500 on the Steelers AFC championship (93/94). I wore my O'Donnell jersey and watched w my friends as they fell 2 yards short.
It was all the money I ever had and I lost it, gambling.
I picked up an autographed Paul Moliter baseball and chucked it thru my basement window (January in MN...not smart). I went upstairs and grabbed Mom's bottle of vodka from the freezer & started mixing shots w Tahitian Treat.
1st gambling loss
1st booze
1st hangover
All in one day.