David Lose, the Director for Biblical Preaching at Luther Seminary, points out what seemingly should have been obvious for the past 2 millennia of Christianity in a column at The Huffington Post: the woman at the well is never described in John 4 as a prostitute, or as a promiscuous woman. Jesus doesn't even mention sin in his conversation with her. [Predominantly male] commentators, theologians and church pastors have consistently described her in terms that purport her to be sexually loose, adulterous, and/or promiscuous, and perceive Jesus' words to her as calling her out of her sin.
Johannine scholar, Prof. Marianne Meye Thompson of Fuller Theological Seminary encouraged her students to look at John with fresh eyes. Although we used Raymond Brown's hefty 2-volume commentary on John, Dr. Meye Thompson did not wed us to his interpretation. Brown's view of the woman at the well, "immoral" was his term, was not matched in the words of John and was not clearly supportable in the sociological and cultural ANE context. When we got to this passage, which I had just worked through for another seminary class, we challenged Brown's interpretation.
It is not at all unlikely that a woman of good reputation might be married a number of times. Men could easily divorce women, but women had little right, if any, to divorce men. If a beautiful woman was barren, for instance, she might be divorced for lack of children, lack of sons, or sadly, for "any reason" a man might give.
There was no "labor market" for women, then. They could be gainfully "employed" as daughter, wife and widow. Few women had sufficient property to exist without the support of men. If a woman wasn't gainfully employed in family endeavors, if she had not the means to survive on her own, and if she was not marriageable, she could depend on the generosity of extended family and neighbors (Ruth, & perhaps, Mary – the mother of Jesus), or become "self-employed" – as a prostitute.
In Robert Kysar's book, John: The Maverick Gospel (Revised Edition), one appendix was entitled, "The Women and the Gospel of John." (I hope he's incorporated this into his 3rd Edition, rather than left it as an after-thought!) Kysar pointed out how remarkable John's presentation of women's faithfulness in the gospel was, for that historical period. The Samaritan woman is discussed in contrast to the disbelieving Nicodemus in ch. 3, as the 2nd evangelist* in the gospel (the 1st was John the Baptist) – an outsider, Samaritan, woman, rejected (the 5 marriages). The text does not support casting her as an immoral person, and in fact, her discussion with Jesus is very perceptive and he treats her with dignity. She not only believes (where Nicodemus couldn't/didn't), but then she goes and tells her town and THEY believe her. (This could count as another strike against assumptions that John depicted her as immoral -- the testimony of women was irrelevant & the testimony of the immoral people was suspect.) Kysar considers the Samaritan woman as the female counterpart to John the Baptist.
Significant women are consistently portrayed as believers in the gospel: Jesus' mother (ch. 2), Samaritan woman (ch. 4), Martha (ch. 11), Mary (ch. 12), women at the foot of the cross (ch. 19), and Mary Magdalene (ch. 20 - 1st witness/evangelist to the resurrection).
The fact that the woman was married multiple times indicates that she was probably not considered a "fallen woman" in her community. (She would have been stoned to death for adultery, for instance – cf. John 8) It seems far more likely that she was barren, or had been married to older men, or had husbands die, or all of the above. That she was living with a man could be that she was living with a relative of her own, or with a relative of a husband, or as a dependent on others (which might explain why she's carting water, but then again, women to this day have the job of carting water in Africa!).
This post continues: Part 2