The Gospels recount an incident where, one day, Jesus was "walking along the borders of Samaria, when he met a woman." Scripture scholars assure us that what is being described here is more than mere geography and more than a simple conversation between Jesus and a Syro-Phoenician woman. A border is a boundary, the edges of something foreign, and Samaria and this woman were what was particularly foreign at that moment.
Samaria was a different ethnicity and a different religion, and the woman a different gender. In essence, the Gospels are saying: "One day Jesus was walking along the edges of ethnicity, religion, and gender, as these there then known and accepted."
Fr. Rolheiser sure has a knack for equivocal expression; the idea that Jesus pushes gender boundaries almost slips past.