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." So I grabbed this little gift box I’d put together and made my way to his place. Inside? Some slick business cards I had printed up for him—each one with a QR code that links 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, totally 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 getting drinks next weekend to keep the good vibes rolling. Obviously, I was down.

Come Friday, we met up 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 wanna stay a while. We started with a flight of beers, trading sips and swapping stories, then dove into some Big Buck Hunter like it was a championship match. Between wings, tots, and laughter, Carson even made dinner reservations for later that night.

Next stop: Olympia Provisions in East Portland. The second we walked in, it was like stepping into another world—dim lighting, plush booths, and that soft classical music that makes you feel instantly fancy. We kicked things off with an antipasti spread that was almost too pretty to eat. (Almost.) Then came the mains: I had the truffle linguine, which was pure magic, and Carson went with a wood-fired pizza stacked with prosciutto, arugula, and shaved parmesan. It was one of those meals where everything just hits. 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 the kind of energy that pulls you right in. More friends showed up, and suddenly it felt like a proper night out. The drinks were strong, the music was louder, and everyone was buzzing with good vibes. There were laughs, random stories, and just a whole 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 out 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 figured we were wrapping things up with a final round at Low Brow Lounge. Last call came and went… but turns out, 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. We're talking top-floor in the middle of the Pearl District, with floor-to-ceiling windows and a balcony that gave us a front-row seat to the entire Portland skyline. It was unreal—like something out of a movie.

Inside, the energy was on point. Music pulsing through the speakers, a perfect blend of pop and electronic, and people just vibing. Robert’s girlfriend poured me a glass of wine, and I ended up posted on the couch having one of those unexpectedly deep catch-up convos. It was chill, but not for long—once that beat dropped, we all found ourselves up and dancing like nobody was watching.

Time got blurry. We laughed, danced, told stories, and just let the night unfold however it wanted. And 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.

As I stepped out of that penthouse and into the early morning air, I just paused for a second—grateful. That night? Absolutely unforgettable. One of those evenings you tuck away in your memory for a rainy day.