Patio Three - The Girl Who Picked Up Pogo

A month has passed since I started my goal of meeting 13 strangers. After my last patio meet-up, which was a bit of a flop and something I actually hadn’t planned for, I found myself wondering, what is my ideal patio outcome? This started as a way to put myself out there, to try new patios, meet new people, but it’s becoming something deeper, a real-time lesson in what makes a friendship stick. If you looked at my bookshelf, you’d see it’s stacked with books about psychology, personalities, and relationships. I’m fascinated by the Enneagram and MBTI. It turns out, a cocktail and a patio can reveal just as much as a personality test, if not more. Side note, Sam is an Enneagram 7 too.

A Girl Named Sam

I started chatting with Sam on Bumble BFF. From our profiles, we had a lot in common, “nerdy shit”, fitness, and “cocktails on a patio” one of her favorite things. We both are here for work, both signed a one-year lease, and as it turns out, we moved in on the same day. Which made me reflect on the day I moved in. There were likely thousands of people moving into a new place that day, each with their own story. What a wonderful thought.

Lost and Laughing

Sam’s from the South and she hates the cold. I assured her this spring chill was abnormal even for the North. We met at Perch, a spot in Wicker Park I heard about through another friend group. It was perfect! The only downside was parking was a bit challenging, but hey, that’s the sign of a bustling neighborhood, so I won’t complain. Perch, with its dog menu, great drinks, and lively patio, was the perfect spot. We laughed realizing neither of us had any idea where we were in relation to home. But it didn’t matter. We were having cocktails on a patio.

The Ease of Connection

Being with Sam immediately felt like catching up with an old friend you haven’t seen in a while, conversation switching effortlessly from one story to another and back again. Just the way I like it. They say we’re the average of the people we spend the most time with. The majority of women I’ve met on this journey so far have been incredible, kind, curious, grounded. Sam was no different. Smart. Stylish. Creative. Thoughtful. Perch itself was a win. The service was great, the vibe was lively, and the dog-friendly menu was appreciated by Pogo. I ordered a Bee’s Knees, it was fantastic. Sam had red wine. Pogo had a chicken protein bowl. She ate the chicken, left the spinach and grains, and then wanted French fries, she is definitely my dog. We were there for almost three hours and had it not been so chilly, I’m sure we would have sat there even longer.

The Moment That Said Everything

About halfway through the evening, Pogo was staring at Sam, she asked if she could hold her, “of course” I said. Everyone bends down to pet Pogo and she gets a lot of love, but this girl, scooped her up and Pogo leaned right into her. It was very sweet. Some people feel a bit like magic. They laugh easily, ask good questions, and see joy in the small things. That kind of connection is the exception. But when it happens, it’s unmistakable. And it reminds me why I’m doing this. I’m not chasing the perfect cocktail or the best first impression. I’m chasing presence. Energy. Ease. Joy.

Friendship

When Sam asked, “Should we make Thursdays Annie, Sam, and Pogo day?” I smiled.

This is exactly why I’m doing this. Not for the cocktails. Not for the check-ins. For the moments like this, where something new begins.

One moment, one stranger, and suddenly the whole summer looks a little brighter.

If that isn’t a reason to stay optimistic, I don’t know what is.