Matilda first appears in A Friend in Deed, walking through Ponyville as Pinkie Pie wishes her "happy birthday to you... in one hundred and thirty two days!" Matilda responds "Pinkie Pie! How do you remember everything about everypony?", and Pinkie says it's because everypony's her friend, then breaks into a musical number.
Pinkie later brings Matilda to Cranky Doodle Donkey's home, having deduced that she was the "special friend" Cranky had spoken of earlier. Pinkie explains that she saw similar memorabilia to that in Cranky's scrapbook before, in Matilda's scrapbook. Cranky starts telling how his night with Matilda at the Grand Galloping Gala was the best night of his life, accompanied by a black-and-white flashback. After the Gala, Cranky comes to Matilda's room, but doesn't find her, though Matilda left him a note which he never saw. He says he spent the rest of his days going from town to town searching for her, and she replies that she was in Ponyville the whole time, and that she always hoped he'd one day find her. She affectionately calls him "Doodle", and Pinkie awkwardly tells her that "nopony calls him Doodle", though Cranky replies "nopony... but Matilda." Matilda kisses him, putting a huge smile on his face. They both enter Cranky's house, and while leaning in for a kiss, Pinkie interrupts them with a song. They both reprimand her, and she apologizes and leaves.