Well, the show first aired when I was still 10, so when I first learned of it and its fandom, I hated it (Because ew, girly stuff and magic and friendship bleh). But in 2012, a lot of fan content found its way on my recommended section on YouTube, so I caved in and watched some. I liked a lot of them, so I hunted for more.
By 2014 I listened to fan music, browsed fanart, watched fan videos, and even read fanfiction. By far the largest part that sealed the deal was Fallout Equestria. On October 17, 2014 I finished reading Fallout Equestria. Sometime later, I decided that I had to actually watch the show. I watched the Cutie Map in a livestream, and the rest is history.