Tis the season of first day of school pictures with smiling children donning new shoes and sporting monogrammed backpacks. My children will be joining the trend in a week, and we cannot wait. We have our pencils sharpened, our new flashy socks picked out (how one shows one individuality in a uniformed place) and our pantries filled.

During these last weeks of anticipation for my children’s first days, the Lord has opened up a window into a very different kind of first day of school. Through friends who live their lives in the throes of the inner city, our family has had the privilege of being connected to people whose lives are drastically different than ours. These connections placed my children and I into the stream of two homeless children’s first day of school.

The children needed breakfast and a place to freshen up and shower and a ride to their first day of school. Excited at the opportunity to serve, we packed brown paper lunches and gathered fresh pencils and folders. We were up and out of the door earlier than we have been all summer, ready for the opportunity to think outside of ourselves and the circle of relative privilege in which we find ourselves.

But the mom didn’t show, and we waited. An hour later, we drove off disappointed and confused.  My older children had two very different perspectives, both of which resonated in my heart. One child, who has a prominent justice sentiment, was angry that a mother would say something and not follow through. The other child, who has a strong mercy sentiment, felt for the children who would have to go to school dirty, unfed and unprepared. The third child had no clue what was going on and was glad to drown our emotions in donuts.

The questions from my concerned and confused children only matched the questions that were churning in my own heart. Why are we picking them up at a gas station? How will they get to school? Do they have backpacks? Did they have clean clothes to wear if they had come over to take a shower?

The same with their thoughts and solutions. This doesn’t seem right. Isn’t there someone we can just call? Can’t we just find them a place to live? 

As they processed, tears welled in my eyes and I realized that I was having my own first. This was the first time that the deep complexities of homelessness and poverty and addiction were really hitting home for me as a mother. Juxtaposing their first day of school with the very different first day that would be coming for my own children, I could not help but be deeply shaken.

We always give donations to school drive supplies; we have even organized them ourselves. We have taken part in after-school tutoring for refugee children. But this was different. This time, the children were children I know and have come to love, children I have spent time with and enjoyed. This time, the mother was not a flat character, one who just needs to get her act together. She is a complex women with a complex past who has her own story that involves competing desires.

After we came home, I saw the brown bags still sitting on the counter with neatly stacked school supplies. I sat on the couch in anger and judgement at the mother, in sadness for the children, in grief for the complexities of the problem. I was disgusted at my own desire for neat and quick mercy opportunities, at my level of discomfort with mercy that is messy because it is relational.

Rather than trying to figure out a solution or make the situation more comfortable, the Lord invited me, for a moment, into His own heart. He invited me to feel the tiniest, tainted speck of what He feels purely and infinitely. He reminded me that when He came to the messy scene of grief after the death of his dear friend Lazarus, before He raised Lazarus from the dead, He sat with the grieving sisters and wept. He felt the weight of the brokenness of this sphere.

We ended up picking the boys up from school and bringing them home for a quick shower. We got to give them their school supplies and lunches and clean clothes and a meal to go. But I didn’t feel good about myself, I felt sober and sad. Sobered that this is an ongoing reality for these boys, sad that I didn’t have a safe place to drop them off. Sad that my heart wants comfortable mercy rather than messy mercy, sobered by the thought of continuing to help this family in a way that meets the complexity of the problem.

In the midst of all the firsts, I am treasuring up a very different first of my own.