The Benson Hotel Lounge might be small, but it’s as swanky as a new pair of Italian shoes.

Compared to our SE Hawthorne sojourn, the Broadway Stumble Zone promised to be cake. A walk in the park. A cakewalk in the park. The cat’s pajamas. It would also be mercifully short, as we were venturing only three blocks from our downtown office. After all, we had to work in the morning, and since we were going out together, no one could call in sick—unless they wanted to wear the mantle of web department wuss.

In an effort to streamline the stumble, we reduced the number of attendees from an unwieldy 14 to a very modest half dozen. Through trial and error (mostly the latter), we discovered that you cannot reasonably come tromping into a bar with more than 10 people and expect a fair shake from the waitstaff—especially with a shabby crowd like me and the drinking buddies, who look like we’d be hard pressed to scrape up a buck in nickels between us. As a concession to making a better first impression, I borrowed a (clean) shirt with a collar for the evening. Grumble, grumble.

We got out of the gates in ritzy fashion with a round at the Benson Hotel Lounge, a swank corner bar tucked into a soaring lobby the size of Safeco Field, and a sterling example of Old Portland sophistication with its stately oak and marble appointments and dozeable banquette seating. The ladies in our group opted for marionberry martinis (don’t get me started on the “what is a martini” debate, please, just this once), but I was feeling like a debonair dude and ordered a Pernod, that potent, milky, and aromatic licorice sipper favored by pretentious nitwits the world over. A couple baskets of crisp and crackly shoestring fries kept the top-shelf booze from burning holes in our guts.

All around us, well-heeled guests were buzzing in and out with bellhops bearing their trunks, valises, and other carrying cases that were in every way superior to the old gym bag that I use while traveling. We eyeballed their interactions and made up tall tales about the most striking citizens.

“She’s just murdered her third husband and now she’s looking to dally for a week or so with a starched and tailored young man who knows at least four different dance steps,” I said, pointing out an impeccably preserved middle-aged hen.

“Ooh, how about him?” Alexis motioned subtly across the room at a tan, windblown-looking fellow who appeared to be freshly decked out from a safari shopping spree at Banana Republic. “There must be some way to get them together.”

“Hmm. He’s a bit khaki, isn’t he?” Garrett offered.

“So khaki … so tacky,” murmured Jenny.

We then proceeded to make up compelling fake identities for ourselves, which I have since forgotten—save that Garrett wanted to be a lion tamer and that I was researching my latest true-crime thriller.

From the lofty heights of smart society we dropped a few rungs to Saucebox, where cubicle drones trading incomprehensible tech jargon, imperious office queen bees, and upwardly mobile slackers were ravaging gloriously hot chicken wings, happy-hour sushi rolls, and lofty drinks garnished with exotic flora.

After the strictly enforced gentility of the Benson, here was a chance to really get our beaks wet. So I pounced on a Kickboxer, one of my most cherished of local cocktails. A semilethal but innervating mix of house-made Thai chili vodka and assorted fruit juices, the Kickboxer, upon first glance, looks like a drink for amateurs, a vivid alcohol delivery system for the lush in a hurry to cast off. But that Thai chili bites deep, and its confluence of fruit and fire works wonders on the after-five psyche.

There’s a constant clamor at Saucebox that makes it hard to do much of anything aside from adding to the din with your own chatter and signaling a waiter for more of the same. A note to drinkers on a budget: the tall drinks take longer to suck down than those served “up” in martini glasses.

Here, we didn’t need to invent personas; we were much the same as everyone else present, minus the designer labels. Like the rest of the crowd, we were employed, still thanking our lucky stars for it, and almost completely bereft of leisure time. That’s why the Kickboxer comes in handy. It’s a liquid holiday that gently inflames our wage-slave senses without the need to pack a suitcase or make hotel reservations.

It was a different story across the street at Bailey’s Taproom, a landing pad for both beer snobs and the beer-curious. To pass as one of the natives here, a patron should be decisive, even in the face of two dozen or so beers you’ve never heard of. I chose the sampler, four-ounce glasses of five different brews. It’s also a handy method of determining the current state of your flavor profile, whether it’s stout, pilsner, or a malty little gem somewhere in the middle. At the moment, my heart belongs to Belgium.

“Lots of board-gamers on the premises,” Harold noted. It’s true. Bailey’s boasts a definite rumpus-room vibe, and the clientele tends toward stocky builds, unruly facial hair, and low-hanging cargo pockets. In other words, me.

And then along comes Mary’s Club, our final destination. Our party was neatly divided gender-wise, and two of the ladies were strip-club virgins, clearly nervous about confronting clothing-optional members of their own team. It was time for the ol’ coach to deliver a pep talk.

“Strippers at Mary’s look like real women,” I told them. “No added sweeteners, artificial colors, or bonus rooms. Just friendly and naked—like the good Lord intended.”

“How naked?” asked Megan the intern.

“Nothing on but the jukebox,” I returned.

The joint is family owned and run primarily by women, the daughter and granddaughters of Mary’s patriarch Roy Keller, who bought the place in 1954 and turned it topless in 1965. It was dark and cool inside and not too crowded. A redheaded stripper named Tori, whom we all promptly fell in love with and later described to co-workers as “a tattooed Botticelli pinup girl," was working the stage accompanied by Tom Waits and the Cramps. A clear throwback to slithery old-school burlesque bump and grind, Tori kept us enthralled through three rounds of Budweiser apiece and all the folding money in our wallets.

As we prepared to part company, the nudie newbies felt proud, invigorated by this ubiquitous Portland rite of passage. “I never thought I’d go to a strip club,” one of them told me. “It was actually pretty cool. I wish Tori was our friend.”

And in a nutshell, that’s the point of a Stumble Zone, venturing outside your comfort boundaries and getting a better idea of who you are, who they are, and who we are. Our little world brought that much closer together through a mutual love of cheap beer and tattooed flesh. I mean, really. Living in Portland and ignoring the strip bars is like moving to Montpelier and not being a fan of pancakes.