Jesus’ positively pure-hearted way of relating to women was outright scandalous by comparison to their men-first-and-foremost culture.
In his interaction with the woman at the well he broke all the rules regarding religious, ethnic, and worst of all, gender biases. An argument could be made that it was to her that he first clearly disclosed his identity as Messiah. Later he held a one-on-one Bible study with a female friend who sat at his feet and soaked up everything he taught. (Women had no such personal access to rabbinical teaching.) And after he rose to life he chose a group of women to make the announcement of his resurrection to the male apostles. He thereby demonstrated a new and radical precedent for gender equality.
The boxes in which the genders had been packaged for centuries were torn open and would no longer hold them. Equality becomes the new normal for those who choose the upside-down way of Jesus.
[An excerpt from my book: WHAT ON EARTH? Considering the Social Implications of Jesus’ Sermon on the Mount]