NO because he is just a cartoon and therefore doesn't have any real emotions.
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sai has no emotions because Donzo (one of my least fav characters) trained him in the hidden mist villlage. he trained in a way to forget all his emotions. So....he cannot love ino back,or love naruto and sakura..his comrads.
That was in Naruto the Movie 6 - Shippūden Movie 3, Inheritors of the Will of Fire
Sai does not wear glasses.
Naruto meets Sai right after returning from his mission to save Gaara. In the manga that would be book 32.
Sai joins team 7 in Naruto shippunden episode 34