Back in Jr. High, we used to log into BBSes and played LORD and BRE and the like. Or we'd log into Octopode which was a local chat BBS and flirt with girls online
Then in 1995 I won $10,000 in cash in prizes on a TV phone-in gameshow on YTV called Destructo Brother's Loot, in which I used the $4000 that I had won to buy my fancy schmancy P75 (which was literally obsolete in two weeks when the P90 and Win 95 got released). Got Cadvision soon thereafter (14.4kbps ftw!) and have been in awe of the Intarweb since.