If God the Father suffers, wouldn’t the blessed souls in Heaven suffer as well? If so, what has happened to Heaven? We go from one vale of sorrows to another?
Shifting gears…
Suppose I myself suffer (whether from injury, illness, financial ruin, or whatnot). Do I want my loved ones to also suffer? Do I want sadness to invade their souls? Do I want my wife, mother, and daughter to basically say, “Well, Geof is suffering, and we love Geof. Therefore we will suffer, too.” Heaven forfend. I want them to be utterly joyful. Their suffering does not help me. I want their help, as far as they can give it; not their suffering. In fact, their suffering would probably make them less capable to help me. And would it not be a doubtful thing to hope that one’s loved ones suffer simply because one was himself suffering?
To anyone who has closely read the seven Harry Potter novels, I put forth this observation: Harry Potter suffered throughout the novels. He was like a lump of iron ore forged over seven years into God’s perfect sword to defeat Voldemort. In the last chapter we see Harry risen above all the anger, doubts, judgmentalism, and suffering that had afflicted him. All of that wasteful emotion had been purged out of him. He was serene, impassive. He calmly confronted Voldemort with truth and with an entreaty that he repent. (The movie is not faithful on this point, turning their final confrontation into the two of them blasting each other with special effects.) Precisely because Harry in this last chapter is no longer afflicted by sadness, anger, and all the rest, he was full of love and strong to save. If he had still been weepy, angry, etc., then Harry could not have defeated Voldemort.
In short, I do not think anything is to be gained by supposing God and the saints in Heaven weep, nor in hoping/expecting our loved ones to do so here on earth. Instead, much would be lost.
The Heavens are not heartless because they shout for joy. Rather, we are heartless because we do not join them.