She's In Portland (2020)

College buddies are the best, or at least they are most of the time.  You get to meet up at reunions, weddings of old friends, and you get drunk and reminisce about the good times.  Well that is unless both of you are envious of the other one and think each other has it better, then you just compare and contrast lives.  For the married with children, house in suburbia, stuck in an office job that he hates Wes (Tommy Dewey), he can't get far enough away from the things he holds dear, or thinks he holds dear... For his best friend from college Luke (François Arnaud), who is aimless, unemployed, can't keep a woman in his life, and spends most of his time drunk on the couch in his one bedroom shithole, he can't get far enough away from himself...  Two guys with basically the exact same background, living two completely opposite lives, thinking the other one has it better; the grass is always greener, so to speak.  When Wes decides to go surprise Luke with a visit to try and reunite him with his long-lost love in Portland, they go from SoCal to Oregon on a journey that has them discover more about each other, the skeletons they are keeping in the closet, what they want for their future, and whether or not long-term fidelity is sustainable, but She's in Portland...  So the only way to find out if true love exists for Luke, is to get up there and see if she's feeling the same way.  Along the way though, these two college buds get into some severe shenanigans, including Wes getting rolled by a sexy grifting duo, which includes some whale tail action from Augie Duke!