Conversation so far:
Who was Alvin and the Chipmunks' Simon Seville?
Simon Seville is the tallest and the middle brother of the Chipmunks.
What can you tell me about Alvin and the Chipmunks' Simon Seville?
In addition to having an IQ above that of Einstein, Simon Seville possesses a dry sense of humor and a keen wit.
Who did Alvin and the Chipmunks' Simon Seville sing with?
Simon Seville sings with Alvin Seville and Theodore Seville for Alvin and the Chipmunks.
Did Alvin and the Chipmunks' Simon Seville have any struggles?
Did Alvin and the Chipmunks' Simon Seville have other siblings?
Simon Seville's chipmunk brothers are Alvin Seville and Theodore Seville.
Are there other interesting aspects about Alvin and the Chipmunks' Simon Seville besides his IQ and brothers?
Simon Seville is often implied to have a crush on Jeanette Miller, as she is like him in many details.

Question: did they ever date?
Self-contained rewrite: Did Simon Seville and Jeanette Miller ever date?