Dear Dear is an Easy Allies meme that originated on Kyle's second stream of "Harry Potter and the Chamber of Secrets," a movie tie-in game developed for the PlayStation 1. It is a phrase often said by Kyle either for fun, or when something bad happens.
Dear Dear came to be on April 13, 2018, when Kyle was playing a Harry Potter game for his Friday stream. It originated during a rhythm mini-game Kyle was doing with Harry Potter character Giledroy Lockhart, in which Kyle had to time his button presses with what was appearing on the screen. Kyle, experiencing difficulty with the game, decided to cool off and take a water break without having paused the game. Because of this, the game was registering that Kyle was missing all of the button presses, and Lockhart had unique dialogue expressing his frustration with this. While most of it seemed to fit with his typical voice and persona, one of them --"Dear Dear"-- was said in a deep and gravelly voice that Kyle (and Twitch chat) found amusing. He then continued to repeat this phrase throughout the stream, causing both Kyle and chat to latch on to it, resulting in it's lasting meme status.