Olive You Forever: A Dirty Martini Odyssey

Behind the bar, I found purpose again—by caring for others when I wasn’t sure how to care for myself. In this work, I’ve learned how the smallest details—a chilled glass, a folded paper plane, a mezcal pairing board—can make ordinary moments extraordinary. But this year, for my partner Rebecca’s 30th birthday, we took that care on the road. Or more accurately, on a barstool. 

We called it the Dirty 30 Martini Tour. 30 dirty martinis, made by 30 different bartenders, across 30 different bars. What started as a cheeky idea became a six-week celebration of flavor, friendship, and the culture of bartending in St. Louis (and Chicago, too). But like all good stories, it didn’t begin in a bar. 

The First Dirty Martini 

The first time I ever had a dirty martini—truly had one, not just a sip—was at Rebecca’s house. I was wary. She had been steeping jalapeños in vodka for an untraceable amount of time and described her concoction as a “spicy dirty martini.” I was scared it would burn my eyeballs off. Worse, I didn’t even like olives. 

But I liked her. And when someone makes you a drink with that much intention, you drink it. 

That gesture wasn’t about the cocktail. It was about connection. Rebecca has always extended thoughtful hospitality in the smallest ways, even before that drink. Our first date started with homemade coffee before a trip to the farmers market. It’s how she shows love: attentively, generously, without pretense. On our first date, I actually cried because of how at home I felt with her. Later, she told me that she liked how comfortably vulnerable I was with her and she wanted to do anything to preserve that. 

Over time, dirty martinis became a staple in our home. And when it came time to celebrate her 30th, I wanted to create something memorable, not just one big night out, but an entire odyssey. 

Making the Tour 

As a bartender, I don’t get many weekends off, so our martini tour happened in between service shifts. Sundays, Mondays, Tuesdays, and the occasional post-shift detour. I made a master list of bars based on where our friends worked, classic cocktail joints, and places we hadn’t yet explored. Some stops were planned; others were spontaneous. 

We introduced ourselves with a little speech:

We even brought scorecards, created with a rubric inspired by Difford’s Guide and Cocktail Codex. Nerdy? Absolutely. But it added structure, intention, and respect for the craft of each bartender we met and allowed us to standardize our judging. Some were nervous, some were excited, and others went full throttle. 

As Rebecca later reflected: “We gamified the service experience but gave the bartenders full control—something many in the industry don’t often get to enjoy from patrons. It became a way to co-create, not just order.” 

We brought a rubric to every bar, but what we were really bringing was a chance for bartenders to play, flex, or surprise us. 100% on their terms. 

Why Our House Dirty Martini Works 

And on our own drink, Rebecca noted with a grin, “A third of the bartenders said it was the first time anyone had ever ordered the wet, spicy, dirty with gin and mezcal martini we were asking for. That felt… significant.” 

So here’s our evolution of the classic: a bold yet polished riff that honors the Martini’s timeless structure while layering tension and contrast in every sip. Built on the foundation of spirit, modifier, and seasoning, each element plays a deliberate role: 

• Gin brings a bright, juniper-forward base with citrus structure — crisp, aromatic, and grounding. 

• Mezcal offers earthy, vegetal depth with a subtle smokiness by adding dimension and tension. 

• Serrano-Infused Vodka elongates the base while delivering clean, focused heat and a tingling mouthfeel 

• Dry Vermouth acts as the bridge and offers subtle sweetness, acidity, and herbal complexity that ties the base spirits together. It softens edges, lifts aroma, and creates continuity. 

• Olive Brine provides umami-rich salinity, the classic dirty element that deepens and grounds the drink. 

These ingredients work together because they resonate on the flavor wheel. It’s green, briny, and resinous. The sweet acidity of vermouth rounds off heat, the aromatics mirror the complexity, and acidity lifts the richness of brine. Like pairing a sweet wine with spicy food, it’s all about balance through contrast.

At its core, this martini is structured, savory, and stirred with intention. A little dirty, a little fiery, and undeniably ours. 

Hospitality in Action 

Every stop taught me something new about what makes a martini great and what makes a bartender special. Whether it was Jeff and Alex Henry’s unintentional spring huarache and martini combo, or Rowda at Monteverde in Chicago slipping us a skewer of 6 hand-stuffed blue cheese olives without being asked, we felt seen. 

Rebecca observed, “By engaging thoughtfully with bar staff, we found that our service was consistently above average. We weren’t just ordering drinks, we were exchanging ideas.” 

Some nights we were joined by friends. Other times it was just us, sitting at the bar, sipping slowly and eating snacks to pace ourselves. We documented ingredients, took photos, and always, always tipped well. 

Our favorite moments weren’t the fanciest. They were the most human: 

• Haley, who split one martini into two glasses to make it easier on us to share a martini.

• Ben, sharing off-menu stories, special liquor picks, spice ratios, and candied & pickled serranos. 

• Osito, with a surprise pairing of chicatana ants and salsa macha alongside a smoky, pine-forward martini. 

It wasn’t always perfect. One bartender shook our martini with one hand while cashing someone out. A couple of spots had a meal requirement to sit at the bar, so we left those behind. We wanted martinis! But even the bumps reminded us why this industry thrives on connection and why bartenders deserve more flowers. 

“What stood out to me,” Rebecca said, “as someone not in the industry, is how much influence travels bartender to bartender, not brand to brand. The most meaningful trends don’t start with corporations, they start when one bartender shares something new with another.” 

Chicago Chapter 

We extended the tour to Chicago. 30 martinis, 30 oysters, 30 flowers for Rebecca’s 30th birthday. It felt poetic. Our favorite martini there? Rowda at Monteverde: a stunning Ford’s gin to olive brine ratio (3 ½ ounces to 1 ½ ounces) and the most generous blue cheese-stuffed olives. At The Office, Haley’s glassware was royalty, and her special pour of their house amaro (on tap) was deliciously bitter. At Bisous, Hannah achieved the cleanest dilution we tasted. 

While Chicago certainly has an elevated martini culture, Rebecca also noticed, “Many bars no longer list dirty martinis on their menu, so it opened up real conversations about how their regulars like them, or how the bartenders themselves learned the classic. We weren’t trying to disrupt; we were here to learn, observe, and connect.” 

Chicago’s bar culture felt more fast-paced, but also deeply intentional. I felt inspired. Every time I travel, I come back with a different lens. Not just as a bartender, but as a guest. 

The Final Dirty Martini Tour Stop 

To end the tour, we hosted a house party for about 40–50 people. I prepped our house dirty martini, hand-painted a photo booth backdrop, and invited every bartender we’d met. Non-alcoholic options flowed freely, and yes, we even served a dirty N/A martini. 

At 8 p.m., we hosted the Dirty Martini Awards Ceremony, co-judged by Rebecca and me. Here are the bartenders that go above and beyond and received bonus awards: 

• Osito at Monstera Mezcaleria for the Dirty Legacy Award: the most unforgettable experience of the whole tour. 

• Evelyn at Sado for the “Olive You Forever”Award: the one you’d go back to again and again. 

• Dave at No Ordinary Rabbit for the Smoothest Operator Award: for most confident, polished, and fun bartender.. 

• Jeff at El Molino for the Past Last Call Award: going above and beyond in hospitality.

• Eric at Vicia for the Dirty Royalty Award: earthy elegance with a dirty grin. 

We laughed, we sipped, we sang along to all the bartender classic songs and lots of reggaeton. And just before the night ended, Mr. Executive Martini shouted: “So who’s throwing the next party?” 

The Dirty Truth 

This tour wasn’t just about dirty martinis, it was about making time. About turning simple moments into something meaningful through care, curiosity, and connection with one another. 

It reminded me that hospitality is an act of love, whether it’s behind the bar or across a shared cocktail. That bartenders don’t just make drinks, we hold memories and forge connections. And when you really love someone, you find every excuse to celebrate them…sometimes even with a six-week tour, 30 bars, a scorecard, and a martini in each hand. 

From the first jalapeño-laced sip to the final toast in our apartment, this journey was flavored by something bigger: 

• A deeper understanding of my craft 

• A renewed appreciation for savory cocktails 

• A clearer sense of what I value, both in a drink and in a relationship 

It taught me that love, like a good martini, is built on balance, contrast, and intention.

It’s wild that olives and vermouth brought me closer to the person I love. That brine and boldness helped me live more honestly. That this thing I do behind the bar continues to shape who I am beyond it. 

And through every pour, every olive, every rating, we got to say it again and again: olive you forever.

Daniela Pedraza is the bar manager at New Society in St. Louis and serves as The Forum’s Food & Beverage Editor. This is the first part of her series exploring the culture and ritual of drinking and mixology.

She was recently named the Best New Bartender in America by VinePair, a national honor recognizing her inventive spirit and bold approach to modern mixology.