Alright children, gather round – Cuffing Season is upon us, and we must prepare.

For the uninitiated, Cuffing Season is a wildly cynical (yet apt) term for the millennial tendency to “couple up” at the onset of fall. You may have been bumping Drake’s “Nice For What” at the club all summer, but once the leaves start to turn, conventional wisdom dictates that it’s time to willingly handcuff yourself to a partner and hunker down for the winter.

While the efficacy of the Cuffing model is somewhat up for debate, there’s no question that fall is an appealing time to lean in to the trappings of coupledom: pumpkin patches & hayrides, harvest-themed weddings, cozy nights in, lazy Sunday afternoons spent watching football.

But what then becomes of the Un-Cuffed amongst us? For those who work more than they date, the coming of fall can sometimes feel like a perverse inversion of the parable of The Ant & The Grasshopper – having danced all summer, the Grasshoppers are now coupled up and cozy, while The Ants are left to trudge alone through the cold.

If you find yourself in that latter camp, this playlist is for you: twenty-odd tracks of mellow, feelingsy shit in the grand tradition of FridayNightsAlone. Some of these tracks are real old, some are brand new, and many of them are from local artists here in Portland. So put in your earbuds, zip up your jacket, and head into the woods with me. There are no cuffs out here.