A: As you mentioned in your question, Paul uses the term a “holy kiss” 4 different times near the end of the letters he wrote to the Romans, Corinthians, and Thessalonians. (Peter also mentions a “kiss of charity / love” in 1 Pet 5:14.)
In Bible times, when two people greeted each other, or were leaving, a “kiss” was often given as a way to show love, affection, and friendship between them. We see examples of this in the Old Testament. Friends David and Jonathan “kissed” before departing (1 Sam 20:41-42). Laban “ran to meet” Jacob, and greeted him with a kiss (Gen 29:13). Esau did the same thing with Jacob (Gen 33:4).
In some cultures today, primarily in the East, we still see people practice this. This “kiss” is almost always between one man and another, or one woman and another, and not between different sexes. The “kiss” is generally done on the cheek, although at times it is done on the lips. I have read that this custom was also practiced in the West until around the 13th century, when it was for the most part abolished. Today, in the West, we primarily use a handshake or a hug instead of a kiss.
In the New Testament, we see Paul adding the word “holy” to this “kiss” to distinguish it from the common “kiss” of “love and affection.” A “holy kiss” was a way for a Christian to show “brotherly (or sisterly) love and affection” for a fellow believer in Christ. It was a way to express unity and fellowship. It was also called “holy” because there were times when the “kiss” was not “holy.” There were times when it was not sincere, genuine, or an expression of “love and affection,” but instead it was done deceptively, offensively, or sensually.
We see several examples of this in the Bible. When Judas betrayed Jesus, he did so by “kissing” Jesus as a sign to the mob that He was the one to be arrested (Mt 26:47-49)(Mk 14:43-45). In the Old Testament, Joab pretended to greet Amasa with a “kiss,” but instead stabbed and killed him (2 Sam 20:8-10). (Also see: Prov 27:6)
On the other hand, we also see examples of what a “holy kiss” should be. Jesus mentions that He was not greeted with this type of a “kiss” (Gr: philema) in (Lk 7:45). Fellow believers “fell on Paul’s neck and kissed him” as he prepared to leave (Acts 20:37).
While some take this saying of Paul’s as a command that needs to be done, most agree that we do not “literally” need to be giving other believers a “holy kiss.” I believe Charles Hodge explains well what Paul likely meant: “It is not a command of perpetual obligation, as the spirit of the command is that Christians should express their mutual love in the way sanctioned by the age and community in which they live” (Hodge – An Exposition of the Second Epistle to the Corinthians). In other words, as said above, today in our culture, a handshake or hug might suffice for “Christians to express their mutual love” for each other.
One other way this “could” be interpreted is like if I wrote a letter and ended it with, “give your family a hug” or “tell your wife hello.” This doesn’t mean that “everyone” is now commanded to do this, but instead I, just like Paul, am simply speaking specifically to the people I am writing the letter to (See: Rom 16:3-15).
***Note: Justin Martyr mentions that in his time (100 – 165 A.D.), a “holy kiss” was done before the Eucharist (perhaps connected to Mt 5:24). Some sources say that in Bible times, a newly baptized person was given a “holy kiss.”
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