Here is the thing though, despite his low-key nature and proclivity to keep a straight-laced outer image, Smithers is not as dull as his cabinet meeting attire and dull palette would make you think, like Burns there is somewhat a duality there regarding his social life, but it’s not nearly as boisterous as Burns’ duality ( which is everything about the man.)
We see aspects of his earlier social life during the episode I Married Marge ( season 3) when not only do we learn that for the first time ever in the series’ history that his first name is Waylon, but he is a notorious frat boy from the Alpha Tau chapter of whatever college/university/tech happened to house him.
shots provided by fyspringfield
Jump to a few seasons forward to Homer the Smithers ( season 7) and we see the extent to how much of a wild nightlife Smithers tries to have despite being magnetically pulled towards the well being of his boss, mentor and secret lover back in Springfield. Smithers tries to live it up on the private gay resort encompassing rowdy and lively activities to try to dampen his mind from separation anxiety, but it is ineffectual (so much that in one of the deleted scenes, after the meaty man-pyramid of power topples into the speedboat one of the gym bunnies asks him if he is thinking of Mr. Burns again.)
Not only does that happen, but later we find out that Smithers on the sexual side of terms cruises for love mostly with older men (he’s a gerontophile, as proven with his carpooling with Dewey Largo (See Homer Run, season 17) and answering to Abe’s false ad in Gorgeous Grandpa (season 25,) but does enjoy a bit of similarly aged men as seen with John (Homer’s Phobia, season 8,) and the occasional looker here and there in the comics.)
And we come to a conclusion, Smithers tries to play it straight (in more than one sense) to distance his private life from his real life (again I can hear you going well, duh in the background) with varying and usually blatant shades of transparency - it’s like he wants to only appear straight just not to break conservative norms and usually out of fear because of said conservative roles - Smithers is nary a rabblerouser nor a radical, as he tries to keep his head down to prevent issues from stirring up and to appear aloof. This was probably a great source of anxiety for him in the past, and he learned to deal with it just to stay way more in line than what would be considered usually normal for any person ( considering this is why he went to Maison Derriere just to avoid fighting with his parents again, which was probably the root issue with his sexuality identification early in life, along with being bullied at school from the likes of Homer and others*) on the opposite end of the spectrum, playing the consummate apple-polisher and rule follower in school he probably ran into even more issues along that path, making him shockingly aloof, until he just learned to keep his mouth shut completely like a whipped dog ala Pavlovian response to wedgies, beatings, draconian punishment and other forms of torture. Because of this starkness, he tends to polarize himself quite unnaturally, even going as far as marrying someone early on in a lavender marriage ( and I say it is a lavender marriage because Smithers never has been shown to have bisexual tendencies and tends to shrink away from women who bare any sexual or romantic inclination towards him.)
From this episode Bart After Dark, we are given the first glimpse into how much of a personal hell Smithers’ early life was assumed to be and probably is. We aren’t given nary another taste of his tragic leanings until the later episode Bye Bye Nerdy (season 12) when Homer and Barney team up to pummel a much younger Waylon in the hallways of the campus.
But, despite the security that playing it straight provides to Waylon, he knows that it is living a lie, he recognizes that it is a great dishonor not only to himself but to other LGBTQ+ people and throughout the whole ordeal tosses out enough hinting that only the attuned can pick up on it. It’s like he wants to break free from stigmas of the antiquated stereotypical American “expectation,” but has issues with that identification, grappling with that titan, the self-struggle within being tugged at the corners of his judgmental appendages very much like the quartered man being drawn between four horses. Those situational mores of what he was taught, what has kept him alive for the past 20 some years, and what he identifies with, and what he thinks is the moral right of humanity. He doesn’t hate that he is gay - Waylon has long accepted that factor in flying colors ages ago, and we see him boldly becoming more open with each new season - but hates the stigmatization that it piles upon his back akin to the dead weight of a crucifix. This is why he vehemently fights for any form of equal right, but on the other side doesn’t want to bring any direct attention to himself - Tapped Out’s Level 54 Ruth Powers walkthrough proves this when Smithers suggests to Burns that equal rights in the workplace for women is a step forward, including equality for people with varying sexual orientations, piggybacking that notion on top a personal issue, a place of understanding and internal endeavors.
This is why we see him so upset with Moe in the episode Flaming Moe (season 22) because Mr. Szyslak not only actually tramples on Waylon’s personal struggles and makes a mockery of it, but Smithers himself is reminded of the issues he had to deal with (and to some little affair, still does) opening his psychological scar into a wound again, misleading others who still struggle and believed in his direction. Smithers is very much like a mother hen looking out for the well being of the flock, whom turns into a shrewd rooster when said fox raids the henhouse.
The glut of self-indulgence within sex ( again, we don’t know how much he has on a basis, but the interview mentions that he cruises, so I can surmise it’s quite a bit) is to distract and numb those feelings outside his being, the external forces creating and nailing down that toxic barrier of self-loathing, and inadequacy. Going to clubs and partying is like his own personal protest, and one that is self-destructive in some cases. He’s not a party monster, but does enjoy nights of excess on occasion, usually seen when he is depressed (again, Homer the Smithers and Flaming Moe.)
* On the flipside of this, we will forego the theory right now (to save space) that Mr. Burns is perhaps the major safe haven in his life, from past and present and thus one of the pillars believed to be holding up the building of his adoration for him. Burns may have been one of the few people in Waylon’s life to provide security and stability in his routine and social outlook - not a father figure per se, far from it, but more of a mentor and dare I say, perhaps an early ‘gay icon’ - who helped him accept and identify with the things considered ‘unusual’ and ‘effeminate’ as “normal,” and as we also can point out a bigger bully who bullies the bullies - being that powerful force to reckon with to make up of his own personal shortcomings.
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