I Was the Classiest 80-year-old Man in Kindergarten
Exactly 25 autumns ago, I was gearing up for my first day of Kindergarten, and I had great expectations. I lived in Weston, Connecticut, which is beautiful and forest-y and full of thin women who don’t wear makeup and retired songwriters and tics and windy roads.
I was only five, but I’d seen other girls. Other girls wore dresses. So, I wanted to wear a dress on my first day of school. My mom wouldn’t let me, though, because she had already picked out an outfit that was “chic” and “classy” and “sophisticated.”
It wasn’t those things. 
Only an 80-year-old man would appreciate this getup. Tucked in argyle vest? Starched dress shirt? Charcoal, pleated tuxedo pants? Seriously?
Look at that photo again. It’s real.
So, I just started homeschooling my five-year-old this week, and I went into it with more great expectations. So did she.
We have her enrolled as a homeschooler under the umbrella program of a local school we like, so we had to go to the school to meet the umbrella lady who is in charge. My girl’s “first day of school,” so to speak.
I picked out what I thought was a chic, classy-looking, sophisticated outfit. Because mothers care about these things. It was green houndstooth fabric with criss-cross straps, embroidered flowers, and matching bottoms. Adorable.
Ever didn’t agree. Her eyes instantly moistened (her crying-on-command skill is truly impressive) and I could tell she was trying so hard to be obedient, but feeling so disappointed inside.
“You have to obey Mommy,” I said. Right away, the 80-year-old man photo popped into my head.
I remembered what it felt like to have my Kindergarten clothes expectations crushed. I remembered what it felt like to wear that man suit that was the color of sadness. I remembered the humiliation of seeing my neighbor, Hannah, bounce toward me in her dress that looked almost exactly like 10,000 pink, lace doilies sewn together with thread made of rose gold fairy hair.
“You know what, Ever?” I called from the other room, “Pick out something you like for your first day. I want you to wear something that makes you feel pretty on your special day.”
In that moment, I figured that letting her win the battle would save her from one of a million heartbreaks she will experience in this life, so full of letdowns.
She walked into her umbrella interview feeling nice and shiny, but I didn’t solve any sort of deep, spiritual problem by letting her wear the pink butterfly dress she chose.
She will continue to want life to work out, and often it won’t. She hopes for nice and shiny. Some days are awfully argyle. I so often hope life will be magical and it so rarely is. Even when it is, the magic is fleeting.
But, this is good.
It’s good to remember that my expectations of whimsy and seamlessness and doily dresses will miss the mark and even when I do get a taste of things-working-just-right, the feeling of “YES - THIS IS THE PERFECT OUTFIT” is so short-lived.
The only great expectation that will never let me down is Jesus. He exceeds the hype - in a way that even my off-the-charts hopes can’t come close to. He lets me rest from my search for magical moments. He helps me know a love that can’t be earned. He trades in my tucked in vest.
I delight greatly in the Lord; my soul rejoices in my God. For he has clothed me with garments of salvation and arrayed me in a robe of his righteousness… - Isaiah 61:10 I will, of course, try to facilitate a happy childhood for my daughters, but it won’t be magical, and when I really think about it, I don’t want it to be. I want my daughters to know and see, early on, that God is the only one who can meet their expectations. I hope they see that Jesus is the one who can make them feel special. I hope they get to rest in Him. But, mostly, I hope they never tuck their vests into their tuxedo pants.