I think this is a fair cross-examination. The author really wants to tie this back into "American loneliness" but I would posit that being a magazine columnist is one of their largest roadblocks to casually making friends.
I have a hard time believing that most people, in a social context, would be turned off from continuing to engage in someone because they are a magazine columnist. Personally, were I to witness someone writing off a whole human being because of such a normal job, I'd make sure to curate that person out of my life.
Esquire basically makes their living off running inflammatory pop culture columns that range from "mildly titillating" to "purely objectifying". They're politically hated by conservatives and liberals, and are nearly indistinguishable from a tabloid in terms of content alone.
I curate my friend group to not have these sorts of talents among them.
I had a knee-jerk reaction to reading this comment, thinking it was perhaps a little too snarky.
But then I went and actually read the story, and it does sort of stink of this kind of intellectualization and overdone analysis that I feel would make it very challenging to make meaningful connections with others.
But isn't that the point of writing an article like this?
We're not reading someone's diary; we're reading someone's homework, and the assignment was "go out and make a friend in a month, and then write about it in an insightful and critical way."
Sure, maybe that was the assignment. But I think overanalyzing your attempts at making friends will get in the way of you making friends. To me it reads as if the author was beginning to drive herself mad by repeatedly reminding herself of each of the tiny mistakes she had made. I don't think that's going to help you make friends.