Is anal retentive hyphenated?

It’s 10:30 p.m. I just got home from a concert. I have an essay to write. It’s time to dash something off quickly. Fortunately, last night my muse suggested that I put this topic on my list of forthcoming essays, so here we go.

Back when I was in college [1], one of my roommates was reacting to one my many picky comments about language use (see, for example CV vs. Vita and asked me: Sam, is anal retentive hyphenated? I believe that my response was something like the following.

It depends on how you use it. If you use it as an adjectival predicate, as in Sam is anal retentive, then you need not hyphenate. However, if you use it as an adjective, as in Sam is an anal-retentive editor, then you need to hyphenate. Otherwise, you might be misinterpreted because adjectives bind to the right.

For some reason, all of my roommates started laughing. When they calmed down, they explained to me that my answer revealed that I meet at least one of the definitions of anal retentive. That is, the question was intended as rhetorical, and my decision to answer further emphasized that I am a person who pays such attention to detail that it becomes an obsession and may be an annoyance to others [2].

However, I will note that if one follows with the Freudian analysis (at least according to Wikipedia), I clearly am anything but anal retentive, since one should also exhibit strong characteristics of orderliness.

I’m clearly an annoyance, but maybe I’m an annoyance for reasons beyond just my obsessive attention to detail. Maybe I’m just obsessively picky rather than anal retentive. But Sam, is obsessively picky hyphenated? just doesn’t resonate as well [3].

DF: I expect that this isn’t of quite the right caliber for the next Imponderables. Oh well, I’ll keep trying.

DR: Prescriptive, not descriptive. Always.

[1] The College at The University of Chicago, as I think it’s officially called. The College, for short.

[2] https://en.wikipedia.org/wiki/Anal_retentiveness.

[3] Note that obsessively picky need not be hyphenated, since obsessively is an adverb, not an adjective, and that eliminates the ambiguity of a double adverb.

Version 1.0 of 2016-10-22.