Discovering My Little Pony.

While I probably saw material from My Little Pony, both Gen 4 and earlier, I only noticed it's existence a few years ago.
My first interaction, I think, was during a Skype call with a few of my playmates (I have serious socialization problems, and this is probably the most accurate term), probably during a Minecraft game.
For whatever reason, someone was making fun of Bronies. I had no idea what that was, naturally. Ponies might have been mentioned.
I went with the group opinion. I had no knowledge on the subject, and no reason to argue, and probably wasn't paying a lot of attention, honestly.

Given the Wiki, this was sometime in October or November, 2011, since I am pretty sure Lunar Eclipse was one of the latest episodes when I started.

The second, was someone at school who publicly stated their status as a Brony. I went to a Special Education Highschool, rather small, and so far as I can tell, he didn't receive any backlash for it. He wore pony shirts, had MLP Cover art taped to his desk, and during a free period, talked about Derpy Hooves once.

The third thing was the famous Yogscast, the Gaming group. They have a series of Minecraft videos, and did a short series, "Sunshine of Israpony" that included the Mine Little Pony Mod. I remember thinking that the whole "Everypony, Anypony" thing was ridiculous and implausible. Later, it confirmed my understanding on how Languages are Artificial and learned, but that's not relevant at this time.

Eventually, I decided that if the Yogscast thought it was ok, and someone at school did so as well, it might be worth looking into. It didn't go over that well.

I tried to watch the Pilot. I failed. This happened several times. It probably took me a week to actually force myself to watch the whole thing. It took at least 3 tries, maybe up to 7. Not sure if it was tried every couple of hours in a day or over a week or what.
Eventually, I managed to watch more than around a minute, then a few minutes, and eventually managed to build up enough momentum to reach the end of the first part. At that point, I was able to watch the rest. I was probably hooked at that point. When I reached the scene in the second part where they Elements of Harmony Manifested from Twilight's Speech, I got tears in my eyes. I had my new interest. Very few things seem to have emotional effects on me. Highly painful injuries, and Allergies can, pain or misery, but fiction wise, Aside from laughter, I can't recall any.
It felt good, and I wanted to watch more.

Over the next week or something, I worked my way through Season 1, and watched the season finale with Discord. I skipped some episodes, mainly those with Rarity Focus, I think. I didn't like her, and mostly still don't. I can't stand art or fastion in most situations, and prefer practicality. After that episode, I later went onto a Starcraft 2 Forum, for the Mod "Hero Attack" (Which has since been taken down), something I had a lot of focus directed towards for a while. While I had seen Pony Avatars, I realized that I had browsed past someone with a Stain Glass Discord Avatar for several months without realizing it. I found out later just how many people had been referencing MLP Memes without me knowing. 20% cooler in 10 Seconds flat indeed.