Kassandra & Jacob

Two Midwesterners now living in Portland — one from Sterling, Illinois, the other from Grand Rapids, Michigan — were drawn west by the same things: nature, food, art, opportunity... and, eventually, each other.

They met in January 2025. The chemistry was immediate, undeniable — and then, somehow, life had other plans. Instead of diving in, they spent the next six months becoming close friends, building something grounded, easy, and full of respect. It wasn’t intentional waiting... but as it turns out, it was exactly what they needed.

Choosing to date wasn’t a casual decision — it was a real one. They both knew they were risking something already rare and genuinely beautiful. They took the leap anyway.

A month later, Jacob moved in. Not long after, they found themselves at a concert by Hollow Coves, listening to Blessings — a moment that quietly, unmistakably felt like home.

From there, life picked up speed in the best way. Within six months, they bought an eight-bedroom 1890 Victorian together and set out to turn it into a mid-term rental. For two full months, their parents — Melanie, Cheryl, and Dan — moved in from the Midwest to help renovate. It was equal parts chaos, laughter, teamwork, and a lot of cooking — and somehow, it only made everything stronger.

Part way through the project, Jacob planned a quiet retreat and proposed beside a rushing river.

Friends and family often describe them as “two golden retrievers in love,” and it’s not far off. They didn’t mean to take the long way to each other — but they’re both certain it made everything that followed even better.