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Last week, I made two purchases off of Craiglist.

The first is a table from a family in Logan Square. When I get there, the husband is wearing a Google shirt. I ask, and it turns out he works on the search team here in Chicago. This leads to several “how many developers does it take to move a table” jokes as we attempt half-a-dozen configurations to get the thing through the front door.

A few days later, I pick up a set of shelves in Bucktown. The woman buzzes me up to the fourth floor, and welcomes me into their home. It’s a beautiful apartment, and it’s obvious that they’re packing. She and I start a conversation as we walk towards the kitchen where her boyfriend waits to help me carry the shelf.

“This seems like a great place. Why are you moving out?”

“We’re leaving the city.”

“Where are you headed?”

“We’re moving to San Francisco.”

And then it happens. I break eye-contact with her, look over, and ask her boyfriend, “Oh, do you work in tech?”

Before the words are out of my mouth, I realize what I’ve done. I try to recover. Boyfriend says “Yeah, I’m a developer at DropBox,” and I immediately look back at her and say “Are you in tech too?”

“Yes. I’m a data scientist.”

But it was too late. We all knew what happened.

I pretty sure that if you asked my coworkers, they’d tell you I’m not an insensitive asshole. They’d probably tell you that I trend towards the more inclusive side of the spectrum.

You don’t have to be an asshole to marginalize women. You can do it with good intentions. You can do it out of ignorance and habit. You can do it out of clumsiness, awkwardness and absentmindedness.

But it still happens. We don’t have to feel shame about it. There’s a lot of inertia and historical patterns working against us. But we need to acknowledge it when it happens.

I didn’t that day. It felt too awkward to bring back up. I made chitchat about other things - the growing tech community in Chicago, the cost of living in SF. But I didn’t address the elephant, and it’s bugged me all week since.