Naruto meets Sai right after returning from his mission to save Gaara. In the manga that would be book 32.
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Sai joins team 7 in Naruto shippunden episode 34
Naruto Shippuden Episode 34
Sai does not wear glasses.
Episode 90 You Can Watch It Naruto-tv.com
Naruto Shippuden episode 54: Nightmare