We should distinguish between things that differ.
1. Considered in Christ, I cannot be more pleasing to God than the perfect Son is perfectly pleasing, Jn.8:29. As Judge, God is satisfied with me. He loves his Son in me.
2. As my heavenly Father, God will be more or less pleased with me, as I am more or less conformed to the image of Christ. Heb.12:6-7 tells us the Father chastens the sons he loves. It seems obvious that while he loves me without fail, still I should be improved through discipline, and his fatherly satisfaction will see a more complete expression.
It is possible to "grieve the Holy Spirit of God," Eph.4:30; so clearly he can be not-so grieved with the same person.
Jn.15:14-15 imply progress in the disciples' relation to Jesus, and the increasing satisfaction he had with them.
So, I say the answer to the OP depends on the specific angle of investigation.