He wept over distresses which He intended to relieve. -John Newton
On hot evenings little boys really need a cold drink. After an intense day of playing I took my son out for a late night Chicken McNugget Happy Meal with a nice cold chocolate milk. 
Poor little guy was so parched that on this occasion he was more passionate about the milk than his super cool toy.
He got two sips.
As we began our journey back home I heard a distraught little boy in the back seat. He had set his milk next to his leg and began reaching into his jolly bag of goodness to retrieve a Nugget (or more likely to marvel at his new toy). Something happened in the transition and the milk found itself on the floor. Yes, my son was crying over spilt milk.
I felt for the little guy but at the same time I’m old enough to remember the adage of “don’t cry over spilled milk”. So I repeated a sentence that I have said numerous times, “Come on buddy, don’t cry—daddy is going to fix it.”
I knew I could get some milk at home. Or if things get to desperate we could easily go back to McDonalds since we only live a couple minutes away. Super-Dad can fix this one. But apparently not fast enough. Saying “wait for my rescue” just doesn’t seem to cut it as a broken-hearted little boy stares at a puddle of milk that should be in his tummy instead of staining the floor of mommy and daddy’s van.
I’m beginning to understand why those words don’t always cut it. Sometimes—even if its really silly—our pain is so intense that all we can really do is cry until mourning has its healing effect. Sometimes tears heal what words can’t.
As the above words from John Newton evince Jesus modeled this perfectly. Just as I intended to clean up the milk and replace it with new so also Jesus intends to wipe away every tear from our eye and conquer or brokenness with his redemption. Yet he even though he knows good and well that these tears are only temporary Jesus joins in them anyway. And they aren’t fake these tears of Jesus. They are motivated by really feeling the sorrow of another.
Yes, Jesus will preach redemption and exhort us to hope. He will tell us “I’m making all things new” and count on us to believe in him. We aren’t to mourn as those who have no hope and Jesus will at times remind us of this. Yet I’m convinced that these exhortations are not accompanied with a disinterested half-smile but instead with cheeks soaked in tears that have miraculously entered fully into the experience of humanity.
So would Jesus cry over spilled milk?
Though he is in the business of changing our affections and our cares and transforming our worries so that they reflect far greater things than spilled milk, I am of the opinion that when my little boy agonizes over spilled milk that Jesus enters into his pain.
Some day, Isaiah, we will live in a world where milk will never spill. Or even if for some reason it did we would probably laugh because we aren’t desperately parched. Some day we will live in a world where we never hunger or thirst and our every longing is fulfilled in Jesus. But we don’t live there yet. In the mean time I want you to know that Jesus weeps with you when you spill your milk. But don’t forget as we all cry together that redemption is coming!
So, sometimes I secretly hope they jack something up. I won’t complain. I won’t even look disappointed. I’ll just humbly hold out my hand and allow them to appease me with a free sandwich.