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Simon is the 2nd oldest brother of Alvin
. He is the smartest of all chipmunks, and is said to be as smart as Einstein. Simon has a relationship with Jeanette, a Chipette. Just like Simon, she is the 2nd oldest of her sisters Britney and Elenor, and she is as smart as Simon too. Simon and Jeanette share a relationship that is somewhat on and somewhat off. Since they are usually shy towards each other, they do not speak much. However, Simon shows Jeanette that he cares and loves towards her. For some reason, SImon needs glasses this is never explained in the comics or the TV show. Simon might be the 2nd oldest, but he is the tallest of all chipmunks. Although, Simon, Alvin, and Theodore are triplets, Alvin is the one in control. Simon does not like some of Alvin's tactics, but they are usually helpful in some of their sticky situations. Simon knows Alvin is the oldest by 5 minutes, however, Simon would probably be a better older brother. When it comes down Simon is always ready to help his older brother, Simon has said before that "we might be the two sides of a coin."