Remember when life was simple, way back in mid-2008? We all wanted the same things—a private island, a Dassault Falcon 7X to spirit us there, and a Fonzworth Bentley to hold a sun umbrella over us as we deplaned. The brass ring was obvious, and it was more like a platinum ring.

Cut to a year later, mid-2009, and hey, life was still simple, only different. The Great Darkness was fully upon us, and we all wanted the same things, they were just other things. Like jobs, homes, hope, and our dignity.

And now? Everything's all mixed up. The recession is over, or it isn't. It's okay to indulge and spend, or it's not. Hairshirts may be so last season, but you still don't want to be the guy whining about the price of jet fuel. Luxury—what it is, what it means—has become a much more complicated, charged proposition. A limited-edition Cohiba is no longer just a limited-edition Cohiba.

Tasked with straddling the micron-thin border between healthy materialism and obscene self-pleasuring, your correspondent, who lives in an ordinary neighborhood in an undersize rental apartment, does not own a car, and puts his Banana Republic chinos on one leg at a time, recently subjected himself to a one-man stimulus package, a series of stamina-testing, high-life-simulating ordeals:

I got a two-hour, four-handed massage; I went heli-fishing in Patagonia; on a plane to Dubai, I drank mature, classed-growth Bordeaux and took a shower. Like any self-respecting quick-money guy, I paid full freight only if unavoidable, mooching whenever possible.

And between alternating surges of guilt (less than you might think), greed, and bliss, I found myself reckoning with a pleasing, if uncomfortable, insight: The crowds are thinner during a recession.

The Four-Handed Massage
Mandarin Oriental hotel, New York City
$782 (including tax and tips)

The minute I lied to Wafa, my masseuse, I glimpsed the new ambivalence about luxury from the inside out. She had asked whether the massage was a gift from someone, and I said yes, suddenly realizing how obscenely self-indulgent it would appear for me to have bought the experience for myself.

Wafa used the word decadent to describe the Oriental Harmony Journey, a two-hour, four-handed rubdown offered at the Mandarin Oriental in Manhattan. An hour-long massage performed by one person at a fancy spa costs maybe $150. This cost almost $800.