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Ephesians 4:30 (NASB)
Do not grieve λυπέω the Holy Spirit of God, by whom you were sealed for the day of redemption.
What is Paul warning Christians not to do - exactly?
I am hoping for support from any of Paul's writings (other Biblical authors, or even the wider corpus of Greek literature), that might illustrate what he means, or what might have inspired him to employ this expression.
Ambrosiaster, a 4th century commentator whose identity is somewhat mysterious, was commenting on the Latin version and not the Greek version of the text, but I think his explanation is still relevant:
The Holy Spirit rejoices in our salvation not for himself, since he has no lack of blessedness. But if we have disobeyed the Spirit, we have grieved the Spirit. His work in us is cut short, just when he wishes us to belong to life. Yet he is not grieved in such a way as to suffer in a literal sense. For God the Spirit is invisible and not subject to physical suffering. When Paul says the Spirit is “grieved,” he speaks metaphorically on our account to show that the Spirit leaves us to our own self-will when we have, so to speak, wounded him by despising his admonitions1
In this case, one could almost drop "frustrate" here, I think: the Holy Spirit is grieved because we are disregarding what is beneficial for us and following our own will. Paul lists what grieves the Holy Spirit in the surrounding verses: Let no corrupt communication proceed out of your mouth (v.29), eschew all bitterness, and wrath, and anger, and clamour, and evil speaking (v.31).
Chrysostom, commenting in Greek, also touches on the relation between disregard and grieving the Spirit:
This is a particularly awful and fearful saying. It reminds us of what he said to the Thessalonians: “Whoever disregards this disregards not man but God.”2 … If you say an arrogant word, if you strike your brother, you have not merely hurt him but have grieved the Spirit. He contrasts such arrogance with the benevolence of God in order to sharpen the admonition.3
It seems, though, that the verb λυπέω is also used to simply mean to be sorry or feel sorrowful. It is used in this sense, for example, by Paul in describing mourning the loss of someone who died:
1 Thessalonians 4:13
Οὐ θέλομεν δὲ ὑμᾶς ἀγνοεῖν, ἀδελφοί, περὶ τῶν κεκοιμημένων, ἵνα μὴ λυπῆσθε καθὼς καὶ οἱ λοιποὶ οἱ μὴ ἔχοντες ἐλπίδα.
But I would not have you to be ignorant, brethren, concerning them which are asleep, that ye sorrow not, even as others which have no hope.
The same word is also used (in the Septuagint) to express sorrow/grief as a sort of disappointment, as in:
Genesis 4:5 LXX
ἐπὶ δὲ Καιν καὶ ἐπὶ ταῖς θυσίαις αὐτοῦ οὐ προσέσχεν. καὶ ἐλύπησεν τὸν Καιν λίαν, καὶ συνέπεσεν τῷ προσώπῳ.
But Cain and his sacrifices he regarded not, and Cain was exceedingly sorrowful and his countenance fell.
In secular writings, the word is, according to Lidell-Scott, used to mean "vex", "distress", or even to "harass" in a military sense, as well as to cause emotional pain (follow link for examples).
1 Commentary on the Epistle to the Ephesians, IV.30
2 1 Thessalonians 4:8
3 Homily XIV on Ephesians
Ephesians 4:30 - What does Paul mean by “grieve” the Holy Spirit?
Ephesians 4:30 (NRSV)
30 And do not grieve the Holy Spirit of God, with which you were marked with a seal for the day of redemption.
A dedicated Christian can grieve the holy spirit if he is overcome with fleshy desires and by doing ungodly traits, Paul implores his Galatian brothers to walk by the spirit.
Galatians 5:16 (NASB)
16 "But I say, walk by the Spirit, and you will not carry out the desire of the flesh."
Galatians 5:25-26 (NASB)
25 "If we live by the Spirit, let us also walk by the Spirit. 26 Let us not become boastful, challenging one another, envying one another."
Paul explains to Christians (Ephesians 4:25-32) how to conduct themselves and thus avoid grieving God' spirit.
Ephesians 4:25-32 (NRSV)
Rules for the New Life
25" So then, putting away falsehood, let all of us speak the truth to our neighbors, for we are members of one another. 26 Be angry but do not sin; do not let the sun go down on your anger, 27 and do not make room for the devil." 28" Thieves must give up stealing; rather let them labor and work honestly with their own hands, so as to have something to share with the needy."
"29 Let no evil talk come out of your mouths, but only what is useful for building up,[a] as there is need, so that your words may give grace to those who hear." 30 "And do not grieve the Holy Spirit of God, with which you were marked with a seal for the day of redemption."
31" Put away from you all bitterness and wrath and anger and wrangling and slander, together with all malice, 32 and be kind to one another, tenderhearted, forgiving one another, as God in Christ has forgiven you."
I believe the question was meant within the context of the word rather than the actual meaning of the Greek "λυπεῖτε"translated "grieve" or saddened" A correct translation of the verse says "by which you were sealed" (NRSV ,NAB Jubilee, Darby , NWT ) whilst an incorrect translation says "by whom you were sealed". Which one do you mean? To me it means the former, or to act in accordance with what the spirit represents. (Galatians 5:22-23)
Ephesians 4:30 - What does Paul mean by “grieve” the Holy Spirit?
To grieve the Holy Spirit may lead to an outright blasphemy of the Holy Spirit. The grieving of the Holy Spirit is felt in us when we stumble, and acts as a warning to us to stop our faulty behavior. If we don't act on the grieving, the Holy Spirit leaves us and evil spirits attach themselves to our conscience instead, leading us into the next stage; the blasphemy stage. As long as we linger in this next stage there is no forgiveness available to us, because we are not interested in seeking it. Blasphemy means to despise. To blaspheme the Holy Spirit is to brazenly despise God's commandments.
Num 15:15:27-31 (NIV) “‘But if just one person sins unintentionally, that person must bring a year-old female goat for a sin offering. The priest is to make atonement before the Lord for the one who erred by sinning unintentionally, and when atonement has been made, that person will be forgiven. One and the same law applies to everyone who sins unintentionally, whether a native-born Israelite or a foreigner residing among you.
“‘But anyone who sins defiantly, whether native-born or foreigner, blasphemes the Lord and must be cut off from the people of Israel. Because they have despised the Lord’s word and broken his commands, they must surely be cut off; their guilt remains on them.’”
Thus, to grieve the Holy Spirit means to upset the Holy Spirit through unholy behavior. When the Holy Spirit gets upset he grieves. If we are sensitive enough to feel this grieving we grieve too and start working on changing our behavior.
