According to Osho, Uddhava failed because he was a pandit—a man of concepts—while the gopis were lovers aflame with direct experience of Krishna. Words, doctrines, and messages cannot quench the thirst of love; only presence can. Krishna sent Uddhava not to teach them but to be taught: that scholarship is useless before love’s hunger for the Beloved, which refuses anything less than God Himself.
Because the gopis were in love and had tasted Krishna, a scholar’s talk was like giving a cookbook to the starving—they wanted Krishna himself, not explanations.