Wes and Luke, who have been friends since college, feel like they are both stuck in their lives. Wes is married with kids and has a demanding job, while Luke is an artist who feels unfulfilled in his personal and professional life.
One day, Wes extends a work trip to Portland and convinces Luke to tag along. Luke's former flame, Thea, lives in Portland and he has always wondered what could have been with her. Wes sees this as an opportunity for Luke to finally let go of the past and move forward.
As they road trip to Portland, they encounter a cast of eccentric characters and meaningful experiences. Throughout the journey, Wes and Luke both confront their own personal issues and reflect on their friendship and what they want out of life.
When they finally arrive in Portland, Luke reconnects with Thea and they attempt to rekindle their relationship. However, Luke also realizes that he may have been holding onto a past version of Thea and that they may have grown apart.
In the end, Wes and Luke both return home with a new outlook on life and a better understanding of themselves and each other.