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I'm missing why this story has anything at all to do with the theme of Hacker News.
that was a great read
I read the whole thing, and I still don't get why anyone is interested. Maeve Brennan, her columns, her life — all of it seems trivial in an especially dull way. Maybe the writer of this piece was unable to convey her interest in as artistic a way as they wished to, and should have told the simple facts instead of trying to construct atmosphere.
The atmosphere is the thing here, along with the character sketch of a person. It's the age-old process of trying to look inside someone's head to feel as they feel.

From the opening few paragraphs I suspect she was one of those people with intense in-person charisma, or as we call it round here, "reality distortion field".

But there's no atmosphere either, just the appearance that an attempt was made to convey it. I'm left baffled over Brennan's significance.
The term Waif was never defined in the article. It's used 6 times counting the title. After googling, it seems to mean a homeless person or low life.
The third definition in MW: : an extremely thin and usually young woman.

Waifish is almost always used with this definition from my experience. I'd even argue the first 2 definitions are archaic at this point.