On Saturday, a fall morning to ourselves, Adelaide and I decided to clean out the closet. For her, this meant taking things as I pulled them off shelves or hangers and placing them in the wrong pile. (If I had a nickel for every time I had to say, “Goodwill on the right, summer on the left.” All the while she bobbled her head, so pleased with her helpful self.)

For me, the entire thing was strangely monumental. I’m a big believer in throwing things out—perhaps a nod to my childhood where, every time we received a new article of clothing we were forced to get rid of something we already owned.  These days, my rule is that if I haven’t worn it in the last year, I won’t wear it in the next year. And so it goes…

There are, of course, exceptions to the rule. Like the shirt I wore to an interview at a top consulting firm—an interview I botched so badly that I hadn’t made it to the elevator before I 1.) started crying and 2.) received a phone call saying they had “decided to go another direction.” I keep these clothes, I guess, because they say things like, “don’t pretend” and “you used to be skinny.”

For some reason, however, this past Saturday I was ruthless. I threw out all nostalgia clothing, including the skirt the badminton player gave me, the cable-knit turtleneck Levi and I wore on our first date, and the shirt boyfriend 4.0 said really “worked” for me. I finally admitted defeat and packed away all maternity clothing, acknowledging that I would not, at any point in the upcoming winter months, be eight-months pregnant.

I threw out almost all of my old work clothes; not exactly sad and not exactly happy that barring the tragic (and then I might be glad for an excuse to shop), at no foreseeable point in my future would I need x number of slacks and y number of blouses. I smiled as I thought about what my friend Sarah said when I told her I had received a tax return from the last time I had a steady income. “Ah, from bread winner to bread maker. How are you?”*

None of this cleansing was as painful for me as it was for Levi, who, on returning later that day had to go through his side of the closet and admit, firmly, that he had gone up two full sizes. I like you better this way, I said. “It’s the Oreos,” he said.

But it’s three days later and the forsaken clothes are lying face down in some dumpster-like drop bin awaiting sorting. And all I can think when I look at our newly organized closet—what with its evenly space hangers and its neatly stacked boxes—is Why?

Why on earth did I give away the nylon black shirt I wore thirteen years ago when Harry {gasp} Connick Jr. responded kindly (and nervously) to my awkward request for a hug.

I meant to keep it as just a reminder that sometimes, everything in the world does work out in your favor.

Dang. I should have kept the cable-knit turtleneck too.