Well, that depends.
Jesus is strong when we are weak, as the Bible tells us, so I imagine instead of breaking down crying with us, he’s next to us comforting our pain, sheltering us from the storm, making sure were OK and don’t fall away.
Alozje Stepinac once said, “when they have taken everything from you, leaving only your two hands, put them together and pray, then you will be at your strongest”. A man is very much more connected with Jesus when he suffers, especially when he’s down on his knees with his final strength. Jesus hears us, and he is definitely concerned.
I think he cries more when we sin, or maybe I’m relating him too much to his (our) Blessed Mother, who is often associated as doing the same thing. When we sin, they look down at the world with tears.