In second grade there was, as I remember him, a pale and speech-impeded boy whom I will call "Luke." Luke was a star competitor in the race to adult insecurities, which he sampled for me via whiny interrogations contrived to extract the future of our friendship. “Are you still my friend? How about now?” For my brute amusement, I occasionally told him no just to watch his expression sour, which must have been my grade school vengeance for his nasal perseverance.

And before you condemn me, may I at least say that I quickly recanted every time. Now you may condemn.

Ultimately, I was the only one who tolerated him, not that I did an amazing job of it. What it mainly brought me was, aside from friendship, the cloying responsibility of maintaining Luke's self-esteem, which was not fair to either of us — me, for self-evident reasons; him, because his only friend was constantly annoyed. What's more is that he did not learn to improve upon his anxieties. I enabled him and, in retrospect, kept him on a kind of leash.

Sounds kinky, right? What happens in elementary school stays in elementary school. Or it pops up again twenty years later and you write about it.

Well, Luke was the first in a long parade of socially inept friends who gravitated to me for reasons I am still trying to understand. I think it is a matter of niceness. Instead of constructively criticizing or outright dismissing, I have too often reserved my feelings about clingy friends and allowed my frustration to come out in passive-aggressive gestures that confuse and hurt other people.

So really, the title ought to suggest that faux-nice guys never finish, because they will forever endure people they do not actually like in order to preserve their feelings. It's a twisted sort of kindness that is only excusable until you realize you're perpetuating it.

As usual, the morally right thing to do is stupidly difficult and quite awkward (who invented this dumb system anyway?) You need to level with these friends, if you have them, or else move on in such a way that they understand you no longer care to interact. That is, help or take off. You're not doing them any favors by maintaining a facade and dragging them along.

Your continued docile friendship will imply that they are behaving acceptably and that there is no need to change. Keep in mind that this is about people who have very few (if any) other friends as a direct result of their dysfunctions. Not simple incompatibilities, but extremely annoying and distancing traits that pretty much only you endure from them.

Shifting a bit, I once tolerated a very rude coworker for the better part of a year because I was afraid to create conflict. Conflict could have meant trouble in my job, or increased hostility from the person who was already a problem. This dude was practically my only coworker (skeleton crew night shifts), so we spent a good deal of time together alone in a vehicle.

Having struggled with my self-esteem and my sanity for that time, it was an overdue relief to finally snap at him on my final day of employment, which I can gladly report shut him up.

The point being, real kindness has limits. Beyond those limits sits a dark sea of suffocating tolerance, which only a dedicated masochist need explore. If I were made to relive my time at that job, I would without a doubt confront him at the first.

Nothing was worth the manipulative abuses of a volatile jerk. And in the case of the unfortunate friend, maybe no one else will ever befriend them. If this is the case, I think they are still better off miserable alone — the alternative being that the two of you are upset together. Tandem bicycles, anyone?