A Supposedly Fun Thing I'll Never Do Again is a comedic essay by David Foster Wallace about a one week trip aboard a cruise ship in the Caribbean. It is also the title essay of a collection of non-fiction writing by Wallace.

In the namesake essay, Wallace wittily describes what he sees as the middlebrow excesses exhibited on a cruise ship. His ironic displeasure with the professional hospitality industry and the "fun" he should be having unveils how the indulgences of the cruise turn him into a spoiled brat, leading to overwhelming internal despair.

Like much of Wallace's work, the essay is a tour de force of bravura writing style, with extensive use of footnotes throughout the piece for various asides.

Another essay in the same volume takes on the vulgarities and excesses of the Illinois State Fair.

Excerpt

"... advertisement that pretends to be art is, at absolute best, like somebody who smiles warmly at you only because he wants somthing from you. This is dishonest, but what's sinister is the cumulative effect that such dishonesty has on us: since it offers a perfect facsimile or simulacrum of goodwill without goodwill's real spirit, it messes with out heads and eventually starts upping our defenses even in cases of genuine smiles and real art and true goodwill. It makes us feel confused and lonely and impotent and angry and scared. It causes despair.

^{This is related to the phenomenon of the Professional Smile, a national pandemic in the service industry; and noplace in my experience have I been on the recieving end of as many Professional Smiles as I am on the [cruise ship] Nadir: maitre d's, Chief Stewards, Hotel Managers' minions, Cruise Director -- their PS's all come on like switches at my approach. But also back at land at banks, restaurants, airline ticket counters, on and on. You know this smile: the strenuous contraction of circumoral fascia w/ incomplete zygomatic involvement, the smile that doesn't quiet reach the smiler's eyes and that signifies nothing more than a calculated attempt to advance the smiler's own interests by pretending to like the smilee. Why do employers and supervisors force professional service people to broadcast the Professional Smile? Am I the only consumer in whom high doses of such a smile produce despair?}

^{Who do they think is fooled by the Professional Smile?}

^{And yet the Professional Smile's absence now also causes despair. Anybody who has ever bought a pack of gum at a Manhattan cigar store or asked for something to be stamped FRAGILE at a Chicago post office or tried to obtain a glass of water from a South Boston waitress knows well the soul-crushing effect of a service workers scowl, ie. the humiliation and resentment of being denied the Professional Smile. And the Professional Smile has by now skewed even my resentment at the dreaded Professional Scowl: I walk away from the Manhattan tobacconist resenting not the counterman's character or absence of good will but his lack of professionalism in denying me the Smile. What a fucking mess."}

(Wallace, 1997. p289)

Reference

• Wallace, D. F. (1997). A Supposedly Fun Thing I'll Never Do Again. Little, Brown.