The Time I Went to 5 Bars in One Night

It all started on a lazy Sunday when I thought, “You know what? I’m gonna surprise Carson today.” I grabbed a little gift box I’d put together and made my way to his place. Inside were some slick business cards I’d printed for him—each with a QR code linking straight to his Instagram. Super clean, super clever. He lit up when he saw them, totally hyped, and we ended up chatting about his latest art pieces like no time had passed.

Then, on a whim, I told him I wanted to buy one of his paintings. Without missing a beat, Carson—being the absolute legend he is—gave me a sweet birthday discount. We stepped outside to snap a few pics of me holding the piece like a proud new parent. Somewhere between the shutter clicks, he threw out the idea of grabbing drinks next weekend to keep the good vibes rolling. Obviously, I was in.

Come Friday, we met at Low Brow Lounge in northeast Portland around 6. The place had that chill, unpretentious vibe—craft beers on tap, cozy corners, and that lived-in energy that makes you want to stay a while. We started with a flight of beers, trading sips and swapping stories, then dove into Big Buck Hunter like it was a championship match. Between wings, tots, and laughter, Carson even made dinner reservations for later.

Next stop: Olympia Provisions in East Portland. The second we walked in, it was like stepping into another world—dim lighting, plush booths, and soft classical music that instantly made you feel fancy. We kicked things off with an antipasti spread almost too pretty to eat. (Almost.) Then came the mains: I had the truffle linguine, pure magic, and Carson went with a wood-fired pizza stacked with prosciutto, arugula, and shaved parmesan. Every bite hit. We capped it off with tiramisu that could only be described as divine.

After dinner, the night was still young, so we rolled into Interurban—a two-story bar with an energy that pulls you right in. More friends showed up, and suddenly it felt like a proper night out. Drinks were strong, music louder, everyone buzzing with good vibes. There were laughs, random stories, and just a lot of love going around.

To close it out, we wandered over to the Crow Bar. Total dive, but in the best way. We played pool, jammed to the jukebox, and just enjoyed being around each other. Carson, of course, cleaned up at the pool table like it was his second job. By the end of the night, we stumbled out a little buzzed, a lot happy, and grateful for one hell of an adventure.

We thought we were wrapping things up with a final round at Low Brow Lounge. Last call came and went… but the night had other plans.

That’s when Robert—one of Carson’s friends—hit us with an invite to his penthouse at the Louisa Apartments. Top-floor in the Pearl District, floor-to-ceiling windows, a balcony with a front-row seat to the Portland skyline. Unreal—like something out of a movie.

Inside, the energy was perfect. Music pulsed through the speakers, a mix of pop and electronic, and everyone was just vibing. Robert’s girlfriend poured me a glass of wine, and I ended up posted on the couch, deep in one of those unexpectedly real catch-up conversations. Chill—but not for long. Once that beat dropped, we were all up, dancing like nobody was watching.

Time got blurry. We laughed, danced, swapped stories, and let the night unfold however it wanted. Before I knew it, the sun was hinting at a comeback. I pulled the ol’ Irish goodbye, slipping out quietly while the party was still glowing.

Stepping out into the early morning air, I paused for a second—grateful. That night? Absolutely unforgettable. One of those evenings you tuck away for a rainy day.