Cities to break your heart in: Portland, OR


This was sent in by a reader who asked to remain anonymous.  It’s about how a certain city can be perfect to “wallow” in after having your lover leave you for a two-bit hack of a poetry teacher.  I encourage you all, dear readers, to comment.  What city do you think is the best to drink yourself to near-death while pining over lost love?  There will be more to come on this topic next week…

3374412652_b28a5d4807The winter comes in around November and just sits on your face for the next six months.  It’s during these never-ending rainy winters that one can find dark and depressing, lovesick meaning in just about everything he sees.  Soggy McDonald’s napkins stuck to the pavement; a shoeless hobo with a cardboard sign that reads, “I just want my childhood back”; a pregnant mother smoking menthols; snobby Reed students on Burnside in coffee shops drawing sketches of coffee cups and wondering if This Feeling will ever go away; your wet shoes and socks and cuffs of jeans dragging on the sidewalk; a chest cold that just won’t go away; postcards in the stationary stores with pictures of tropical islands that exist somewhere.  This is a nice backdrop for drinking pint after pint of microbrews, listening to the hiiiissssssssss! of passing cars on the wet streets, trying to dredge up enough enthusiasm to flirt with your pointless date at The Pied Cow – the only thing you share in common is the fact that you screwed last night in a bar bathroom.  Well, that and ennui.  Yes, Portland is a great place for wallowing.  All those gray shades and weary folk who say they have SADS.  Sads, huh?  Of course.  Sads.  Is it the weather, or is it that she left you for an unpublished poetry teacher?

2 Responses to “Cities to break your heart in: Portland, OR”

  1. 1 sarah

    How about Detroit? There is something about the abandoned buildings, the graffiti, the bums, the unemployment rate soaring that just breaks your heart.

  2. 2 heartbrokedaily

    Woof. Dee-troit. I’ve had a few low moments there, for sure. I’m fairly certain it’s where they send you when you die if you were bad. Some good rock n roll has come out of there though.

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