Illustration by Dan Page
Illustration: Dan Page

Something about the place just wasn’t right.

It might have been all the neon, which gave the room a disquieting reddish hue. Or the tatted-up bartender, who was so attentive it bordered on insincere. Whatever the reason, despite its killer burger and an impressive beer selection, when I left West on North on a Wednesday evening last September, I knew it would not be my local bar, the place where everybody would know my name.

For two years, I’ve been on the hunt for a new favorite tavern. My family’s move to the western edge of Bucktown took us barely two miles from our Ukrainian Village condo. But when it came to watering holes, I was in a different world.

After more than 15 years in my old hood, I knew exactly where to go there if I wanted to, say, hang out with Polish third-shifters or day-drink with day traders. I knew which bars had decent jukeboxes, which ones poured stiffer-than-usual cocktails, and which didn’t take their karaoke too seriously. Now I felt rudderless. I didn’t want an anonymous booze hall. Nor did I need to go full Norm from Cheers. I just wanted a place where familiar surroundings and interesting characters could help me briefly escape the perils of adult life.

It was proving harder than I’d expected. Green Eye on Homer Street, with its candlelit tables and cool artwork, was a little too hipster. Floyd’s Pub on Oakley had potential, but its yuppie clientele and overall cleanliness lacked edge.

Then, as I strolled down Western one unseasonably warm November afternoon, I spotted a sign with an Old Style logo. Beneath it, a petite 30-something woman was pulling open the creaky, accordion-like security gate of a ramshackle red-and-black storefront. I took it as a signal: time for a drink.

“Come on in!” said the woman enthusiastically.

Who was I to argue?

She led the way into O’s Tap, an unmarked dive on the border of Bucktown and Logan Square, and flipped a couple of switches. A pleasant glow illuminated the bottles behind the handsome wood bar.

I plopped down on a stool and soaked up my surroundings. The place reminded me of my favorite wayward uncle’s basement rec room. There was a pool table squeezed in the back and one big (but not too big) TV in each corner. The musty smell of the previous evening’s spilled drinks still hung in the air. It was just about perfect.

The bartender introduced herself as Kat. Her eyes were friendly, but something about her steely gaze told me she didn’t take any shit.

“It’s Thursday—all our draft craft beers are four bucks,” she said.

Within seconds, I was sipping a You Got Yr. Cherry Bomb, a sour from Mikerphone Brewing in Elk Grove Village that was one of half a dozen inviting options scrawled on a blackboard. I took a swig and “Gimme Shelter,” my favorite Stones song, kicked in.

It might have been my slight buzz, but two beers into my first visit I knew this was the place where I belonged—or, at least, where I wanted to belong. But to become a regular, I had to lay the groundwork. So every time Kat gave me change, I tipped her generously. (And when I left a few hours later, I casually dropped a fiver. I might not be a Pritzker, but I’m no skinflint, either.)

It was easy to make conversation with Kat because I was the only one there. But I didn’t patter on about my problems—I kept things upbeat. I told her I was from the neighborhood and what kind of beer I liked. Our conversation seemed natural. After an hour, I almost felt like a regular.

Then a young dude with a hipster mullet strode in. Without saying a word, he was greeted with what I can only assume was his usual: a tall PBR draft. Kat gravitated to him, and they kibitzed like longtime pals. I went to the bathroom, and when I returned, the music was off and the two of them were giggling at It’s Always Sunny in Philadelphia reruns. I laughed along, but it was obvious where I stood in the pecking order.

Before I left, Kat whipped up a drink of her own creation—she said it tasted just like Skittles—and walked right past me to deliver him a free shot. Could I ever become that guy?

I returned a few nights later and claimed the same barstool, figuring repetition would breed familiarity. But Kat wasn’t working. Jasmine was.

“Do I know you?” she said as I ordered a Lagunitas Pilsner. Not yet, I thought.

The staff change threw me off, but the casual vibe at O’s was starting to feel comfortable. Within minutes, I was deep in conversation about Al Franken with a lanky 60-year-old fellow nursing a Miller High Life and a manic bald guy in his 40s who claimed to be a former standup. That’s what a good bar can do: bring strangers together. And when I noticed the mulleted guy sitting nearby, he raised his glass and gave me a nod.

A few beers later, I felt energized by the camaraderie. And my steady tipping and polite banter inspired Jasmine to give me my last beer for free. Score!

Several weeks passed, and one December night things started to fall into place. My pace quickened as I saw the Old Style sign. I craved the reassurance of my usual barstool. It was Thursday, which, as an aspiring regular, I knew meant $4 craft beers. Kat gave me a big smile when I walked in from the cold.

“Welcome back,” she said, and proceeded to pour me some samples. When I casually mentioned how much I loved the Stones, she fired up “Gimme Shelter.” Coincidence? I think not.

Then, during an intense discussion about season 2 of Stranger Things, Kat noticed my glass was empty.

“Like another beer, Rod?” she asked. The fact that she remembered my name made me downright giddy, but I played it cool. Absolutely, I would.

There was a crowd in O’s that night, and two women, no more than a few years out of college, hovered behind me.

“Wow, you seem like a regular,” one of them said.

Not quite. But I’m getting there.