Monday, Paul and I flew down to LA to meet with Chairman Mom’s product team, and before we left town, we had breakfast with Catherine Connors to talk about more cool stuff we are launching. Even better: It happened to be her birthday!

I ordered pink champagne in honor of her hair. We discussed how great it looks and the reaction of strangers and her kids to the move, and then got down to Chairman Mom business.

This was LA, so there was a very attractive young (YOUNG) couple next to us enjoying brunch and bottomless mimosas in the middle of the day. They could have been on The Hills a decade or so ago.

Just as they got up to leave, the young man, who was not at all bro-y and seemed really sweet, turned to Catherine to compliment her on her pink hair. You know how something starts really awesome and then you just see in slow motion that it’s taking a turn for the worse and you are powerless to do anything about it? That’s what happened next…

“I love your hair”….Turned slowly to…“My grandmother also died her hair pink…” and then…“so, thank you for doing that” as if Catherine was performing a service to grandmothers everywhere.

He walked off and all three of our jaws kinda hit the table.

“Uh, happy birthday,” I said.

“Wow, that went sideways quickly,” she added.

And then we just laughed. I mean, it was basically textbook how not to compliment a woman. As a white woman in her 40s in a city where “older” women are frequently seen as invisible, I felt a small twinge of what women of color must feel when people call them “fierce” or ask to touch their hair.

This guy clearly meant well. He was trying to explain his emotional connection to Catherine’s hair and that he thought she was fearless for doing it, and even though this guy was young, he wasn’t so young that a woman our age could actually be his grandmother so he didn’t mean it literally. But still. Yikes.

I guess if you are confident enough to pull off pink hair in your 40s, you are confident enough to be compared to some guy’s grandma.

Today’s new questions on Chairman Mom:

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