Conversation so far:
who was simon seville of the chipmunks?
In addition to having an IQ just north of Einstein, Simon possesses a dry sense of humor as well as keen wit.
what can you tell me about him?
He is kind, gentle, logical, and at times poetic.
who did he sing with?
originally voiced by Ross Bagdasarian Sr.
In the animated series and film, he was voiced by Ross Bagdasarian Jr.
Matthew Gray Gubler voiced Simon in the live-action/animated film series.
did he have any struggles?
Although Simon tends to disagree with Alvin and even argue with him, he truly loves his brother and sticks by him despite everything.
did he have other siblings?
Like his brothers.
Are there any other interesting aspects about this article?
Simon is often implied to have a crush on Jeanette, as she is like him in many details.

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