“Concerning this thing I pleaded with the Lord three times that it might depart from me. And He said to me, ‘My grace is sufficient for you, for My strength is made perfect in weakness.’ Therefore most gladly I will rather boast in my infirmities, that the power of Christ may rest upon me” (2 Corinthians 12:8-9)
Paul the Apostle’s experience in pleading for the Lord to remove this “thorn in the flesh” brings to mind Jesus’ experience in the Garden of Gethsemane just prior to His crucifixion…
“And now they came to an olive grove called the Garden of Gethsemane, and (Jesus) instructed his disciples, ‘Sit here, while I go and pray’ …Then he returned to the three disciples and found them asleep. ‘Simon!’ he said. ‘Asleep? Couldn’t you watch with me even one hour? Watch with me and pray lest the Tempter overpower you. For though the spirit is willing enough, the body is weak.’ And he went away again and prayed, repeating his pleadings” (Mark 14:32, 37-39, TLB).
We should note that Jesus “…went away again and prayed, repeating his pleadings” within this portion of Scripture. This represents an important consideration for anyone who seeks to determine if it is appropriate to pray repeatedly regarding a need or approach God once in prayer and leave that request with Him. In light of Jesus’ experience in Gethsemane (and Paul’s experience as recorded here in 2 Corinthians 12:8), it seems appropriate to bring our needs to God for as long as they exist or until such time as we receive an answer from Him.
Finally, one scholar offers a wide-ranging and thought provoking analysis of this passage…
“This was not lack of trust, but shows that we can pray about whatever concerns us as often as we feel the need. This recurrent, painful problem taught Paul a great spiritual lesson (cf. 2Co_12:9). I must say here that this account sheds light on the over-emphasis in our day on faith healing being conditioned on the amount of faith of the person needing healing. Obviously Paul had tremendous faith. Also, the unfortunate teaching that God wants every believer healed and delivered from every problem is addressed in this passage.
The requests of both Jesus and Paul were not answered in the way they wanted. God uses problems and sickness in our lives for His purposes (cf. Rom_8:17; 2Co_1:5; 2Co_1:7; Php_3:10; 1Pe_4:12-17). Our needs are God’s opportunity to reveal Himself and His will to us!” (1)
(1) Dr. Bob Utley, Free Bible Commentary 2 Corinthians [12:7] Copyright ©2014 by Bible Lessons International http://www.freebiblecommentary.org/new_testament_studies/VOL06/VOL06B_12.html