Back in '63 I was fresh out of school and into my first job. A pool-playing buddy introduced me to Bob Dylan, Joan Baez, and I was hooked on folk music.
Then he showed me his guitar, a basic 6-string with strings a mile above the fret board. I borrowed his guitar and a book of simple songs and went to work learning to play. When he asked for his guitar back a month later I had to get my own.
Around this time Oscar Brand was hosting Let's Sing Out on TV, and I fell in love with the sound of his Goya 12-string, so I went out and bought my own. That's the only type of guitar I played for the next 30-odd years, progressing through several until I was lucky enough to find an almost new Laskin 12-string at a great price.

Along the way I also picked up a tenor banjo, harmonica (I now have one in every key), a bouzouki, a couple of mandolins, a Larrivee 6-string about 3 years ago, and a mandocello that I liberated from Rick Fielding. I'm still learning to play them all, and at times it seems I'll never get to where I want to be (don't we all say that fairly often?)

Interesting thread, and many similar experiences from you mudcatters.