I called my high school buddy Paul and told him my constraints. He laughed. He thought a minute. He was in.

We met at 6 at a chic bar in Logan Circle, where our quest began -- with beer.

Paul, his co-worker Richard and I each ordered a beer on the patio, which has multicolored lights strung up overhead and is filled with couches, curtains, metal tables and, for some reason, garden gnomes.

Even though, in the District, Pabst Blue Ribbon is holding its own as the hipster swill du jour, I can't help laughing when I see that blue and silver can brought out on a neon tray at Helix. Part of the Kimpton hotel empire, Helix has high-rollers lodging upstairs who mix with office types like me from the neighborhood, who pop in for its happy hour's half-price beers. Once I saw three women in bikinis posing for a photo shoot by the Magritte-esque mural out front. Around here, you never know what you're going to see.

The three of us sat and watched people come and go as we each hashed out our current existential crises. Maybe the world is coming to an end . . . but right now, let's get another round.

By 7:30, I'd spent $4 ($1.50 per beer, plus tax and tip), and happy hour was long over (it's from 5 to 7 on weekdays). It was time for Ben's Chili Bowl.

Now, let me explain something. Richard had just moved to the area. He said earlier he'd go home after Helix, but when he asked, "What's Ben's Chili Bowl?" I knew he couldn't leave yet. "You're with natives. We have to take you to Ben's," I insisted.

We paid the bill and took off up 14th to U street.

Richard got a little wide-eyed on our walk. Paul pointed out the new Storehouse Furniture (a clear sign of gentrification), while across the street, the social services center, Central Union Mission, implored "Come Unto Me" in huge block letters painted on the side. The street's practically a definition of incongruity. As we walked, the light had that perfect sundown softness, making the construction sites look like monuments to Logan Circle's transformation.

Passing the Black Cat, Richard asked, "What is that?" as he nodded at the long line of people snaking against the storefronts. There was obviously a popular band playing, but Paul and I were stumped. When we got to U Street, we heard music and people talking in the jazz clubs and restaurants. Across the street was the awning of the Lincoln Theatre next to the golden arch of lights framing Ben's doorway, the storefront trimmed in jaunty red and yellow.

I like to take people to Ben's, partly because I like the food -- the hot dogs are grilled so they're crispy on the outside, soft and juicy on the inside -- but also for the restaurant's history, its symbolism. I like to remind people that where we're chowing down was once the eye of the storm during the riots of '68, the event that turned U Street's "Black Broadway" into junkie central. Through all the neighborhood's hardships, Ben's stayed open for business, a true survivor.

We walked in and hung back in line for a few minutes. Paul and Richard had given up on the $10 challenge by then, but I was still reading the menu on the wall and totaling my options. I settled on the chili dog, which was $3.10. Paul got one with cheese, which sounded too good to resist, so I went for the Velveeta, too. It cost an extra 35 cents, but it was totally worth it.

We sat for a while in the booth we'd snagged. It was near the door, so we watched people come in. A young couple, looking dazed in sweats, tried to maneuver a huge stroller holding an impossibly tiny baby. A trio of middle-aged women stood outside the plate-glass window, looking in, trying to decide whether to take the caloric plunge. Then a stringy young guy burst in, shirtless, and one of the waiters shooed him out till he put a shirt on. That's the thing about Ben's -- you get all that entertainment for free.

I didn't have a Weekend section in my bag, so we snagged a City Paper from the stacks by the doorway. I wanted to see what famous band was playing at the Black Cat, why all those people were lined up outside the door. I looked it up; none of us had a clue. Paul usually knows all the good bands, and I think I should, so we both lost a little steam, thinking, How had we gotten so old, so fast? We are so out of the loop! Well, at least we had chili dogs in our bellies, and I still had $2.55 in hand.

Paul and I pointed Richard to the U Street-Cardozo Metro stop and walked back to Black Cat. Outside the club, the line was just as long as it had been more than an hour ago. It seemed like every teenager in town was going to the show. That's what I liked about Black Cat back in high school -- with its all-ages shows, you could just drop by and see a cool band any night of the week, even if you weren't 21.

Well, now we're a bit older than that, and we weren't there for the show, which cost more than $2.55. So we casually strolled to the front of the line, peeked in at the bouncer and said those magic words: "We're here to play pinball." We showed him our IDs, he stamped our hands, and we strolled into the Red Room to get our game on. The Black Cat's downstairs bar has a pool table, two pinball machines (Bram Stoker's Dracula and Elvis) and a machine with your choice of Ms. Pac-Man, Frogger and Galaga.

It's possible to go far in the Red Room with $2.55. A more coordinated person could play pinball for hours, racking up points with skillful flicks of the flipper. But not I. I downed 50 cents on a game of Bram Stoker's Dracula and lost within seconds of figuring out where the start button was. I got in a few satisfying thwacks, watched the ball roll, hit some bumpers and made the lights flash, but then the ball would shoot down the middle, right through my flippers. That was a warm-up, I thought, so I tried again. Twice. Losing more and more pathetically each time.

Right. So pinball's not my thing. I thought I remembered how to play Ms. Pac-Man, but it wasn't till I saw Paul strategizing that I realized I was out of my league. So we took a break and scoped out the scene.

Maybe it's from my year in Paris, where people-watching is practically a registered sport, or maybe it's because I'm lazy. Paul does it brilliantly, having honed his skills in Vienna (Austria, not Virginia). We just leaned against the bar and took in the action around us: the indie rockers in black huddled around the jukebox; the goth girls wearing wow-that's-short skirts; people milling around with a lot of tattoos, a few odd piercings.

I got a second wind and dropped my last four quarters into the machine, and Paul and I went head to head on Frogger. Judging from my performance in Frogger, I shouldn't be allowed to cross the street alone. But I wasn't far from my apartment, and, thankfully, I made it there unsquished.

I spent $4 on beer, $3.45 on dinner and $2.50 on arcade games. I had a nickel left and I kept it.

HELIX LOUNGE -- 1430 Rhode Island Ave. NW. 202-462-9001. www.loungedc.com.

BEN'S CHILI BOWL -- 1213 U St. NW. 202-667-0909. www.benschilibowl.com.

BLACK CAT RED ROOM BAR -- 1811 14th St. NW. 202-667-7960. www.blackcatdc.com/redroom.html.

As a teenager, Christina Talcott, a regular Weekend contributor, frequented the Tastee Diner, the Montgomery County Thrift Shop and La Madeleine French Bakery & Cafe (abusing their free bread and bottomless-cup-of-coffee policies).