If we accept (a) that many of Jesus’ disciples had left their wives behind to follow him and (b) that women were included in Jesus’ following (some known in their own right; not attached to a particular male), could this provide the context for Jesus’ strange teaching about divorce?
Given Jesus’ praise of eunuchs and those who have left their wives and houses behind, it comes as no surprise to hear him discourage remarriage. After all, Jesus seems to have an aberrant view on marriage and family.
Could it be that he was discouraging his male disciples (who had left wives behind) from marrying the female followers with whom they traveled? In other words, perhaps Jesus is saying, “So you’ve left your wives behind to follow me; great! But don’t use that as justification for divorcing your wives to marry one of your new traveling companions!” Please keep in mind that "leaving" one's wife behind and legally divorcing one's wife were two very different things - the latter being devastating for many women.
This possible reading would also help to explain this saying, “You have heard that it was said, ‘You shall not commit adultery.’ But I say to you that everyone who looks at a woman [or just "wife"] with lust has already committed adultery with her in his heart” (Matt 5:27-28). Dale Allison has suggested that this saying suggests a moderate form of asceticism on Jesus' part. But maybe Jesus is just trying to keep his disciples from exploiting their newly formed "family".