Amplified John 14:23-24 23Jesus answered, If a person [really] loves Me, he will keep My word [obey My teaching]; and My Father will love him, and We will come to him and make Our home (abode, special dwelling place) with him. 24 Anyone who does not [really] love Me does not observe and obey My teaching. And the teaching which you hear and heed is not Mine, but [comes] from the Father Who sent Me.
Question 1: Why did Jesus say "keep My word (singular)" instead of "keep My words (plural)"?
Matthew 5:19 - God expects for us to obey everything that He said. God's Word teaches us to obey His word, but also how to obey His word.
John 14:10 - God works in our lives to obey Him as we yeild to Him.
Amplified John 14:25-26 25I have told you these things while I am still with you. 26But the Comforter (Counselor, Helper, Intercessor, Advocate, Strengthener, Standby), the Holy Spirit, Whom the Father will send in My name [in My place, to represent Me and act on My behalf], He will teach you all things. And He will cause you to recall (will remind you of, bring to your remembrance) everything I have told you.
Question 2: What does Jesus mean when He said that the Helper, the Holy Spirit, will be sent by the Father in the name of our Lord Jesus Christ?
The Holy Spirit is here to act on behalf of Jesus' interests. He works from Jesus' agenda not ours or his own.
Question 3: What did Jesus mean when He said that the Helper will teach us all things? What, when, how, where, and why?
The Holy Spirit teaches us truth one step of obedience at a time. The Holy Spirit teaches us to look at life from Jesus' point of view, because the Holy Spirit works on Jesus' behalf. The thoughts that we have that are pointed toward Jesus' interests are the thoughts that originate from the Holy Spirit.
Question 4: How does the Helper use our memories to teach us? How can we use our memories to learn from the Helper?
When we are alone, we are commanded to fill our minds with the word of God. When we are in public, the Holy Spirit will direct us by recalling what we have stored in our hearts while we were alone with God. (see Romans 12:2)