A: This is an example where it is helpful to look at the original Greek of the word “boasting” used here. When we do, we find the word “kauchesis” being used. It comes from the Greek word “kauchaomai,” which means “to boast or glory.” “Boasting” can be done in a good way or a bad way. The way we usually think about “boasting” is when it is done in a bad way: (i.e.) when someone is “bragging,” or being prideful about themselves and their accomplishments. However, “boasting” can be done in a good way too: (i.e.) when someone is boasting about God or another person, and not about themselves.

     When “kauchesis” is used in a good way, sometimes a different word is used instead of “boasting” in some Bible versions. For example, with this verse (1 Th 2:19), the KJV / NKJV / WEB translate it as “rejoicing,” the NIV / ASV translate it as “glory / glorying,” and the NASB translates it as “exultation.” These translations also fit with the Greek meaning of “kauchesis.” They also seem to work a little better than “boast / boasting.”

     For example, let’s look at (1 Th 2:19-20) in the KJV:

“For what is our hope, or joy, or crown of rejoicing? Are not even ye in the presence of our Lord Jesus Christ at his coming? (20) For ye are our glory and joy.”

     What seems to work better here: crown of “boasting” or crown of “rejoicing?” To me, Paul is talking about the “rejoicing” or “glorying” they will have one day over the Thessalonians when they are in the “presence of (the) Lord Jesus Christ at His coming.” They will be Paul’s “glory (“doxa“) and joy.”

     Connecting this with the word “crown,” I believe Paul looked at the Thessalonians one day being “in the presence of our Lord Jesus Christ at His coming” as him being the victor of a race (see: 1 Cor 9:24-27, Phil 2:16). Them being there was his “crown.” We see Paul talking in a similar way to the Philippians, and the Corinthians:

(Phil 4:1) Therefore, my brethren dearly beloved and longed for, my joy and crown, so stand fast in the Lord, my dearly beloved.

(2 Cor 1:14) As also ye have acknowledged us in part, that we are your rejoicing (“kauchesis“), even as ye also are ours in the day of the Lord Jesus.

     However, having said this, There are some verses where “boasting” (used in a good way) seems to work and fit better with “kauchesis:”

(2 Cor 8:24) Wherefore shew ye to them, and before the churches, the proof of your love, and of our boasting (“kauchesis“) on your behalf.

(2 Cor 11:10) As the truth of Christ is in me, no man shall stop me of this boasting (“kauchesis“) in the regions of Achaia.

(Rom 15:17)(NASB) Therefore in Christ Jesus I have found reason for boasting (“kauchesis“) in things pertaining to God.

(1 Cor 15:31)(NASB) I affirm, brethren, by the boasting  (“kauchesis“) in you which I have in Christ Jesus our Lord, I die daily.

     And, here is an example of “boasting” (“kauchesis“)  used in a bad way:

(James 4:16)(NASB) But as it is, you boast (“kauchaomai“) in your arrogance; all such boasting (“kauchesis“) is evil.

     And, finally, here is an example where “kauchaomai,” from which “kauchesis” comes, works better translated as “rejoice” or “glory” rather than “boast / boasting:”

(Rom 5:2-3) By whom also we have access by faith into this grace wherein we stand, and rejoice (“kauchaomai“) in hope of the glory of God. (3) And not only so, but we glory (“kauchaomai“) in tribulations also: knowing that tribulation worketh patience;

     This is why looking at a word in the Bible in Greek (or Hebrew) can sometimes help us to understand some verses a little better.

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