"Day 17: Draw a pony meeting someone new/Draw a pony breaking the ice.
When did Yosh and Lilly first meet each other? I'm surprised that I haven't delved too much into this. Let's set the scene.
Several years ago, IronYoshi was extremely down on his luck. He was alone, depressed, and wasn't making enough to afford his home. He would begin looking for a roommate to help him out, but every attempt ended in failure. Who would want to be with someone like him with his tacky shirt and his massive collection of Celestia-related merchandise?
Then one day, he heard a knock at the door, and saw a blue hippogriff with boundless energy and enthusiasm. She introduced herself as Sea Lilly, and she heard about being a potential roommate and was hoping to adjust herself in Canterlot, having netted a job as a photographer and just moved from Mount Aris (she wanted to experience the world, as the hippogriffs had freed themselves from the Storm King's grasp).
Yosh was reluctant at first, he thought she was just a bit too chatty and bubbly, but seeing as how desperate his situation was, he agreed. And thus, a beautiful friendship would be formed!"