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What is the significance of the 'Holy Kiss' during the liturgy?

The holy Kiss symbolizes love, peace, forgiveness, unity, and spiritual reconciliation. The deacon first instructs the people to "pray for perfect peace, love, and the holy apostolic kisses. He then recites the exact words from four of the Pauline epistles: "Greet one another with a holy kiss," (Roman 16:16; I Corinthians 16:20; II Corinthians 13:12; I Thessalonians 5:26); "Greet one another with a kiss of love" (I Peter 5:14). Originally, the kiss was to be given on the cheek; or as in the Coptic Orthodox Church, where interconnecting hands with the congregants standing the closest; following this with kissing one's hands. In general,
the style of greeting with a kiss was used by early Christians and Jews as well. It illustrates a deeper affection than the modern day handshake.

Our Lord identified the errors of Simon the Pharisee, who knew the scripture and customs; but because of his arrogance, was negligent to the protocol, and could not understand the concept of forgiveness. In the same passage, the "sinful woman" demonstrated love, humility, and appreciation for having been forgiven. Just as it was customary to provide water to wash the guests' feet, anoint their head with refreshing oil; so was familial greeting kiss; "You gave me no kiss, but this woman has not ceased to kiss My feet since the time I came in ... "Therefore I say to you, her sins, which are many, are forgiven, for she loved much"... Our Lord then excused her to "Go in peace" (Luke 7:36-50).

Unlike our Church greeting kiss, Judas's to the Lord was an insult above betrayal. "Immediately he (Judas) went up to Jesus and said, 'Greetings, Rabbi!' and kissed Him. However, Jesus replied, "Friend, why have you come?" (Matthew 26:48-50). In the Prayer of Reconciliation, the priest prays "According to Your good will, O God, fill our hearts with Your peace. Cleanse us from all blemish, all guile, all hypocrisy, all malice, and the remembrance of evil entailing death. And make us all worthy, O our Master, to greet another with a holy kiss, that without falling into condemnation we may partake of Your immortal and heavenly gift in Christ Jesus our Lord." It is therefore imperative that we reconcile with our friends and family before proceeding to partake of anything with Christ ("Friend, why have you come?")