And now a meandering, self-indulgent tale that will no doubt warm your hearts and bring a tear to your eyes. Shanna, my undergrad-aged sister, has been dating a guy named "William" for a while now. He turned 21 over Memorial Day weekend. For some strange reason, they didn't immediately hit every single drinking establishment in and around U of O to celebrate. Instead, he remained bar celibate until last Saturday when he could get up here to dive into Portland's plethora of booze holes.

So where do you take a bar virgin from a small Oregon burg that's never set foot in so much as a Red Robin lounge before? Into the heart of the city during Rose Festival for a dose of maximum culture shock.

10:45 PM - The kitsch-drenched paradise that is North Interstate's Alibi Tiki Lounge seems like an ideal first stop. Will's first drink in bar, ever, is a Mai-Tai with cute little yellow umbrella. He's slightly amused by the place but not impressed. Portland's bar scene will have to double the culture wattage.

As we wait for the bill, a mysterious, middle-aged man in a suit plops down at the table next to us. He looks like a balding Agent Cooper and chain-smokes as he stares. I accidentally leave an $8 tip that's quickly whisked away by the waiter. Outside, another mysterious man with a cigarette case lingers on the sidewalk near our vehicle. Two words come to mind: "white slavery."

11:30 PM - We park near the park blocks and hike up to a yuppie Chinese restaurant next to the new Henry's Tavern. There's a gigantic fortune kitty attached to the wall but not a single Asian person in the place. Their Hot and Sour soup is full of mushroom and is quite tasty. Will claims one of the beers tasted like apples. It does not taste like apples.

11:50 PM - We somehow find ourselves in a crowd of bar-hoppers all dressed in mini-skirts. Leering frat-types lean out of the windows of early-90s SUVS covered in dents and blast their approval at them/us. The mini-skirts keep walking and stare straight ahead.

12:00 AM - Somewhere near 4th and Oak they suddenly pour out in a gigantic wave: what seems like hundreds of nude people on tiny, tiny bicycles. Most are men and all of them are wearing florescent helmets and knee pads. They shout and honk bike horns. One drunk guy "asses out" in the middle of the intersection and struggles to hop back on. He's completely nonchalant and acts like riding nude down a downtown street is the most tedious activity in the world. I check the screen on my digital camera. The pictures are blurry and it's hard to tell if the figures in it or dressed or not. See above.

Shanna is delighted. Will sighs solemnly. I want to grab the cuffs of his Columbia Sportswear jacket and shout, "ARE YOU NOT ENTERTAINED?"

12:15 AM - The Shanghai is loud, smoky and crowded. Our table is covered in wet rings, empty gin glasses and a yellow box of American Spirits. We order gin and tonics and wind up with gin and gins. Ozzy rolls out of overhead speakers as hipsters look as disinterested as possible.

12:45 AM - What do you get when you try to enter the City Grill near closing? A pointless but super fun elevator ride. We climb in and our ears pop all the way up to the 30th floor. The box stops and we hear the sounds of laughter and jazz leaking through the doors. Then we go back down. We ride a second time before it dawns on us that the place closes early.

We head for Dante's. Maybe a fire pit and that black-velvet painting of Eve is more Will's style. As we pass the Chevron, two men almost fall out of an ancient Ford while making kissy-faces at Shanna. "I think they like you," I say. She kicks me.

1:30 AM - William's boredom has reached catastrophic heights. I'm running out of time. I may have to comandeer a parade float or destroy a Corvette. We're at the Veritable Quandary and Will looks like he's about to slip into a ennui coma. "Midnight Vultures" is cranked somewhere between 10 and 11. A guy in a suit smokes an endless cigarette and macks on a blond-haired woman. He's got a major case of diarrhea of the mouth and she nods a million times.

2:30 AM - Closing time. I drag them back to 2nd Avenue. I've got one last chance to find something to make Will's night memorable. Downtown Portland has become a Navy-sponsored Pirates of the Carribean. Throngs of drunks pour out of century-old doors and the streets clog with Rose Fest sailors. One has his arms wrapped around two girls in sparkly dresses. He turns to another and shouts "I'M TAKIN' 'EM BOTH HOME, MOTHERFUCKER!" A Gap model bumps into me and starts making strange cat noises. His attention quickly drifts from me to Will. This is sure to make his expression change from 100% boredom to at least 92% boredom, 8% terror. The model raises the pitch of the cat noises and tries to hug him. Will quickens his pace to get away from him. Somehow, he still looks like he's stuck in the waiting room of a Jiffy Lube.

At Voodoo Donut, a guy makes bets with the staff that no one in the room can eat 10 donuts in an hour. No one believes him but is unwilling to take the bet. I mention that it's supposedly impossible to down a gallon of milk in an hour. The guy claims he's done this but even he can't handle to awesome power of ten donuts. I buy a glazed donut the size of a toilet seat and Shanna goes with a Coco Puff donut.

2:35 AM - We join the exodus. The sailor/pirates are making their way to downtown apartments with their "booty." A sailor piggy-backs a girl about to pass out. He has taken the district's shanghai theme a little too far and wears the expression of a marauding Viking. Someone babbles my name a dozen times. I turn around and see a face I haven't seen since middle school. He's wearing a reggae hat and a goatee. I ask him his name, he tells me and he waits next to an open cab door for a response. I can't think of anything so I raise my thumb and say, "You're [deleted]? Really? That's all I got to say, man."

2:40 AM - Back in the car I get glaze all over myself. Sailors, drunks, ambulances and cop cars fly around us in all directions. Will yawns. I begin to suspect he leads a double-life as a spy, a millionare playboy or a combination of the two. Or maybe I'm just easily amused.

Mission not accomplished.