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I understand there's different theories on how many times Jesus' feet were anointed by a woman (most say 2, ie, Luke 7:36-51 and John 12:1-8, and that Luke alone mentions an earlier one). Augustine had an interesting theory that Mary was the same woman both times due to John mentioning her doing this before recounting how she did this. Nevertheless, this isn't my question. My question is whether it was common during Jesus' time for people to do this? How likely is it that two different women both anointed Jesus' feet with ointment specifically out of an alabaster flask and used their hair to wipe his feet?

Dottard
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Genesis 18:4 Please let a little water be brought and wash your feet, and rest yourselves under the tree;

Judges 19:21 So he took him into his house and gave the donkeys fodder, and they washed their feet and ate and drank.

1 Samuel 25:41 She arose and bowed with her face to the ground and said, “Behold, your maidservant is a maid to wash the feet of my lord’s servants.”

Luke 7:44a Turning toward the woman, He said to Simon, “Do you see this woman? I entered your house; you gave Me no water for My feet,

Foot washing was commonly practiced even in Jesus' time. But what about foot anointing?

44b but she has wet My feet with her tears and wiped them with her hair. 45You did not greet Me with a kiss, but she has not stopped kissing My feet since I arrived. 46You did not anoint My head with oil, but she has anointed My feet with perfume.

The "but" signals a contrast:

You   did not   anoint     My head with    oil
she   has       anointed   My feet with    perfume

Jesus contrasted the possibility of the self-righteous Pharisee anointing Jesus' head with the relatively cheap oil against the extraordinary act of the sinful woman's anointing Jesus' feet with extremely expensive perfume.

The contrast shows the woman's act was unusual and extraordinary, not to be expected by the average citizens.

At the conclusion, Jesus declared:

48 Then Jesus said to her, “Your sins are forgiven.”

The whole episode shows that foot anointing was unexpected, unusual, extraordinary, and perhaps unheard-of.

Was anointing people's feet common during Jesus' time?

I doubt it. You anointed a person's head and washed his feet.