I think you may find it helpful to meditate more on the *humanity *of Jesus. Christ fully experienced our sadness, a rich and abiding sadness. It is the sadness of suffering – even if it is later blessed by eternal beatitude.
I imagine he wept for the lost, and for Judas. But he also wept for the saved, that we must suffer; and He wept for sin, that such a sacrifice as his must be made necessary. And He probably wept for the actual stress He was experiencing; this was not a selfish act, but rather an act of great humility.