What makes this long sentence so creepy is that by the time we arrive at its end Schmidt has unwittingly revealed himself to be the kind of creepy guy he ostensibly disavows. I have highlighted some of the structural elements.
Schmidt had had several years of psychotherapy and was not without some perspective on himself, and he knew THAT a certain percentage of his reaction to the way these older men coolly inspected their cuticles or pinched at the crease in the trouser of the topmost leg as they sat back on the coccyx joggling the foot of their crossed leg was just his insecurity, THAT he felt somewhat sullied and implicated by the whole enterprise of contemporary marketing and THAT this sometimes MANIFESTED VIA PROJECTION as the feeling that people he was trying to talk as candidly as possible to always believed he was making a sales pitch or trying to manipulate them in some way, as if merely being employed, however ephemerally, in the great grinding US marketing machine HAD SOMEHOW COLORED HIS WHOLE BEING and that something essentially shifty or pleading in his expression now always seemed inherently false or manipulative and turned people off, and not just in his career – which was not his whole existence, unlike so many at Team Δy, or even that terribly important to him; he had a vivid and complex inner life, and introspected a great deal – but in his personal affairs as well, AND THAT somewhere along the line his professional marketing skills HAD METASTASIZED THROUGH HIS WHOLE CHARACTER so that he was now the sort of man who, if he were to screw up his courage and ask a female colleague out for drinks and over drinks open his heart to her and reveal that he respected her enormously, that his feelings for her involved elements of both professional and highly personal regard, and that he spent a great deal more time thinking about her than she probably had any idea he did, and that if there were anything at all he could ever do to make her life happier or easier or more satisfying or fulfilling he hoped she’d just say the word, for that is all she would have to do, say the word or snap her thick fingers or even just look at him in a meaningful way, and he’d be there, instantly and with no reservations at all, he would nevertheless in all probability be viewed as probably just wanting to sleep with her or fondle or harass her, or as having some creepy obsession with her, or as maybe even having a small creepy secretive shrine to her in one corner of the unused second bedroom of his condominium, consisting of personal items fished out of her cubicle’s wastebasket or the occasional dry witty little notes she passed him during especially deadly or absurd Team Δy staff meetings, or that his home Apple PowerBook’s screensaver was an Adobe-brand 1440-dpi blowup of a digital snapshot of the two of them with his arm over her shoulder and just part of the arm and shoulder of another Team Δy Field-worker with his arm over her shoulder from the other side at a Fourth of July picnic that A.C. Romney-Jaswat & Assoc. had thrown for its research subcontractors at Navy Pier two years past, Darlene holding her cup and smiling in such a way as to show almost as much upper gum as teeth, the ale’s cup’s red digitally enhanced to match her lipstick and the small scarlet rainbow she often wore just right of center as a sort of personal signature or statement. (Oblivion, “Mister Squishy,’ 25-26)
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