My questions related to the text (ESV):

Observation (questions for the head)

1. Jesus tells his listeners that they have heard what from old?
2. People where swearing oaths in what four ways?
3. And what are the four reasons that Jesus gives for why this is wrong?
4. Jesus makes it simple in regards to your communication with God.  What is it?

Interpretation (questions for the head and heart)

1. Where does it say in the Old Testament, “You shall not swear falsely, but shall perform to the Lord what you have sworn”?  Is this a direct quotation or a summary statement?
2. In Jesus’ day, why where they swearing oaths by such places or objects?
3. Were the Jews saying that some oaths were binding and others were not?  How does Matthew 23:16-22 relate to this issue?
4. What is the difference between resolutions, vows, and oaths?
5. How can evil come from oaths?
6. Should people take oaths and swear on the Holy Bible?
7. What about the oaths in Romans 1:9; II Corinthians 1:23; Philippians 1:8; I Thessalonians 2:5, 10;  and Hebrews 6:17-19?

Application (questions for the heart and hands)

1. What are common oaths that people make today?
2. Have you ever told the Lord that you were going to do something but didn’t follow through?  What about those New Year resolutions that you made to God?
3. Jesus just finished teaching on marriage in Matthew 5:31-32.  Do you consider your wedding vows an oath?
4. Please share an example of where someone said, “My word is my bond,” and it blessed you.
5. Do you need to make right on something that you said you were going to do?
6. When you are angry, do you have a tendency to exaggerate and not be completely honest in your speech? Have you had to then in an evil way defend your own exaggeration?

Notable quote(s) from Oswald Chambers:

“Refrain your speech until you can convey the sincerity of your mind through it. . . . Most of us can talk piously–we have the practice but not the power. . . . To call God in as a witness to back up what you say is nearly always a sign that what you are saying is not true.”

On Matthew 5:37 – “Scandal should be treated as you treat mud on your clothes.  If you try and deal with it while it is wet, you rub the mud into the texture, but if you leave it till it is dry you can flick it off with a touch–it is gone without a trace.  Leave scandal alone, never touch it.  Let people do what they like with your truth, but never explain it.  Jesus never explained anything; we are always explaining, and we get into tangles by not leaving things alone.  We need to pray Saint Augustine’s prayer, ‘O Lord, deliver me from the lust of always vindicating myself.'”