In the spirit of avoiding summer boredom, here's my story on how I came to spend $150 of student money on a Leafs jersey:
As a Toronto native, it's hard to say exactly when it all started. When we went to my grandfather's on a Saturday the Leaf game was inevitably on, and the entire family would be present, though my grandfather, mother, and I may have been the only ones actually paying attention. This was at a young age though, I didn't know player names and barely knew how the game worked. I remember I went out to get a mini-stick to play out at recess, the shop was sold out of anything good so I grabbed a Tampa Bay Lightning stick, not really caring which team I got. Of course I was laughed at the next day.
My mom was a Jays fan first and foremost, but when the Leafs made the playoffs she watched intently, and loudly. Once again I'd watch, mostly because of the fact that it often extended my bed-time (once again, very young). I've got a better memory of those days. Later in life I'd go on to yell at the TV with her, I remember cursing Dominik Hasek for looking amazing, laughing at our inevitable defeats of the Sens, and the outrage at Gretzky.
Once I started going to high school hockey pretty much slipped to the backburner in my mind, I missed the heartbreak against the Hurricanes in '02, other things were keeping me busy and I'd only been a casual watcher growing up.
After my grandfather and mom died at the end of grade 12 and I went into university, a few of my old high school friends were watching games together (this would be 05-06) and invited me to come along. Being new in uni and lacking much to do, I started watching games with them. It had been a while, I barely recognized anybody or remembered the rules, but after a while I was heckling Jason Allison and Aki Berg with the best of them. I was really just watching hockey to get out of the house, but seeing it again reminded me of my mom and grandfather and gave me something to do
Once I moved out of the house in 06-07 I was without cable and most of the comforts of home. I'm obsessed with following numbers and generally going neurotic on a hobby, so I switched to watching the Leafs on CBC. What was casual viewing in 06 got pretty hardcore in 07, with the start of the 07-08 season marking me entering hockey pools, going to Leafs/Marlies games, buying jerseys, etc
That's it I guess, pretty unremarkable. While it could be said I've been a fan all my life, I don't really think of it that way, I just didn't follow the game the way real hockey fans did. So I'd say I've been a real fan for about 3 years and counting, and I picked a hell of a time to start watching again (they haven't made the playoffs since I started following the team closely).