“Blessed are the Poor in spirit, for theirs is the Kingdom of God. “
Matthew 5:3

Scriptural Context: Luke 6: 17-26 and Matthew 5: 1-12

Μακάριοι- Blessed/Happy

If you recognize you are not what you should be and long to be the person God created, then rejoice; for wherever there is a lack or void there is also the opportunity for God to fill it. And the person who takes the opportunity to receive what God alone can give, is a person who is filled with His Joy.  The person who doesn’t recognize their short-comings and spiritual poverty remains empty; for such a person has no opportunity to receive God’s blessings and become God’s blessing to others.
(Romans 3:22-23, Isaiah 66:2, Revelation 3:17-18)

The Lord longs to extend His Right Hand to us in grace and mercy “where there are pleasures for evermore“. The obstacles in His gracious path are pride and ignorance. Who is God’s “Right Hand”? The Lord Jesus Christ is the Father’s right hand making intercession for those who place their Trust in Him where there is always the opportunity and hope. (Romans 8:34, Psalm 16:11)

The Lord longs to reveal His compassion to us. (Isaiah 30:18). His first step in revealing His compassion has always existed and before the world was even created His plan was to redeem mankind; “God so loved the world that He gave His Only Begotten Son, so that whoever believes in Him shall not perish but has eternal life”. (John 3:16)

The Lord longs to fill us with His Holy Spirit ; sent to transform and  complete all who are in Christ Jesus. (Philippians 1:6, 2 Corinthians 3:18,Matthew 7:11)

Whenever we are filled with ourselves there is no room for God’s oil of gladness. Therefore, as we empty ourselves in repentance while acknowledging our need for God, He will surely fill us. When we offer ourselves up to Him in Faith, our cup runs over with His Grace, spilling out on others; and in this, the Lord is glorified.
(Psalm 23:5, Lamentations 3:22, John 10:10)

If God did not spare His Son, and gave Him up for our salvation, He also is ready to give us His blessings according to His riches in heaven.  This is the abundant life, Jesus promised. We just need to ask and be open to receive Him.  (Romans 8:32, James 4: 2-3, John 10:10)

Reference: My Cup Runneth Over:
https://www.gotquestions.org/my-cup-runneth-over.html