Usually this question is answered ideologically, trying to claim that Jesus would do whatever the speakers worldview demands. “Jesus hung out with sinners.” “Jesus said I bring not peace but a sword.” “Jesus said judge not!” “Jesus beat money changers with a whip.”
If you really want to answer the question seriously, you have to approach the dual nature of Christ represented in this icon. On the left, Christ the Savior and friend. On the right, Christ the judge and the Law.
He loves all human beings, and he freely offers all of them salvation. He also represents the totality of the unchanging, eternal law. He is the ultimate judge- he doesn’t “look passed” our sins, but he also doesn’t stop loving us in spite of them.
Christianity is not supposed to be easy. You are never at any point supposed to believe “Jesus would agree with me”- Jesus is not entirely on your side, because you can’t
be entirely on his side. “For all have sinned and fall short of the glory of God.” Ultimately, the great challenge is to be able to conceive of Christ in both ways, in every situation, while also being aware that he is also looking at you as you judge and discern. To be able to judge those you love, and to love those you judge, while never placing yourself above them and always judging yourself most harshly of all.
I ponder this icon often. “Christ Pantocrator” is the title.
“Dont criticize or judge other people—regard everyone else as an angel, justify their mistakes and weaknesses, and condemn only yourself as the worst sinner. This is step one in any kind of spiritual life.” - Heiromonk Seraphim Rose