Squick? Oh, it’s some TVTropes term. That’s a bit excessive, it is only mild bemusement on my part.
Why should we presume the person trying to persuade their friend in this example is objectively correct in knowing what is both the appropriate and correct way for their friend to behave?
You can shorten it to: “Don’t be discouraged when your proselytizing of rationalism is ineffective the first time, just be consistent in your message.” Honestly not seeing much of a difference in the article if you replace every instance of “rational” with “Christian.”
I would wonder what is wrong with the guy keeping track of the times I expressed annoyance at losing something, which happens to everyone, and why they’re so myopically focused on tracking every minor incident and turning it into an excuse to lecture me.
I guess, from a rational standpoint, what is the utility of keeping such a boring and condescending person around?