Archive for the ‘stories of heartbreak’ Category

When Sloan called, our three-year, scorch-the-earth relationship had been in the rearview 18 months. I’d high-tailed out of Chicago with nothing but the clothes on my back, a hotel bible and an iPod with a broken screen, that only seemed to shuffle between Huey Lewis & the News songs. Spent two weeks kicking in my […]

“Is this a one-night-stand?” she asked, as I was putting on my cowboy boots, sitting on the side of her mattress, which sat on the floor of her barely furnished sublet. If you have to ask, then that means, yes. “It doesn’t have to be,” I say, “I don’t have anywhere to be until this […]

Hilde had been an alternate reality crush when I was at undergrad in Chicago. She was an exchange student from Hamburg – who, in my daydreams where I imagined myself a wealthy, successful adult – I thought maybe I had a chance with. She was out of my league, but we were friends nonetheless, with […]

“Am I doing it right?” I asked, knowing I was doing it completely wrong. Greta looked over at my pile and acted mock horrified, eyes spread wide. “Wow. You mutilated that one. That’s, like, all stem now. Completely unsellable.” “Shit.” “It’s ok. I won’t tell Micah,” she said. She slid closer and took the next […]

I was wrong about everything but the trip. Roxanne should have come with me., But now I was here in Paris, in the stabby February cold, wrong for all the right reasons. I camped out in a rental apartment in my old stomping grounds in the 18th. I looked for old drinking buddies. No one was […]

Lara, the altar


I didn’t end up in Houston for its extracurricular charms. After 18 months trudging the Canadian tar sands, I wanted to be somewhere warm and vague. I had in mind to offset my carbon footprint by volunteering with a non-profit restoring avian habitats. I wanted karmic validation. What I got was Lara. Three weeks in […]

I sat down next to Kim on an F-train out of Boerum Hill on purpose. I’d noticed her reading Scott Pilgrim Gets It Together on the platform, and I found myself stalking her impulsively. She seemed new to the city, or maybe a tourist, the way her eyes wandered across the mostly empty train, taking […]

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First it was that god damn dos equis guy. My girlfriend said I should be flattered, but what does she know? I’d prefer these advertisers pay some kind of royalties to offset my drinking costs. Ah, well. I rather like this one, anyways.

She wanted me to kiss her that first night, when she gave me a ride back from the Country Night at the Wheel Club.  She called two days later and asked if I might want to hike up the mountain with her. On that walk, and the subsequent trip to Farrell’s ice cream parlour, she […]

I’ve spent a fair amount of time in 12 step programs. A couple tours it was court-ordered. A couple others, I felt really serious about drying myself. Not forever, I had not misconceptions about that, but just for a while and going to meetings helps focus me during bouts with sobriety. A few other times, […]

I’ve been considering replacing this blog with a picture blog, highlighting pictures of beautiful women, reading books. While I continue to chew on my book, is that something readers would appreciate? Here are some examples. (via 1 2 3 4)

A reader, who should remain anonymous, sent this letter simply to share with me, but I, being the voyeur that I am, felt it too raw not to publish. I was especially touched by writer’s profound awareness of her situation. How no resolution will come. And how much that hurts. Enjoy. Dear ex-boyfriend, Happy birthday.  […]

“How can you eat that shit? You know it’s filled with dried pig anuses and cow ankle fat, right?” She’s referring to the pepperoni stick I’m chewing on. Bozeman was disappearing behind us. I’d found a cassette of Springsteen’s Nebraska at the last Texaco. The close-to-setting sun was painting the sky a sentimental color. I […]

The door cracks quietly, as she lets herself out. It’s 5 AM. I doze for another six hours. When I awake, my head throbs. The summer heat in my basement apartment is already unbearable. I limp to the kitchen, pull a bottle of vodka out of the freezer and try to recall last nights bender. […]

Bernadette hated my guts growing up.  I suppose I can see why.  I did break up with her just before our Fall Seventh Grade Activity Night/dance.  In my defense, I was only 12 – and besides, I was really, really high on acid at the time and she just wouldn’t stop talking.  Everything in me […]

I was teaching creative writing, part-time, at a private high school down in Palo Alto. The gig felt pretty humiliating. Here I was – in my mind, one of the premier literary voices of my generation – reduced to helping the children of privilege express their petty, overwrought dissatisfactions with life or, alternately, craft an […]

Sounds at Night


Got this, interesting, anonymous post in the mail this week. Hardly a typical HBD post, but I enjoyed it enough to share with you, dear readers. Enjoy. This is a transcript of an audio recording that my ex-girlfriend sent me to the night that she left to move to Texas for a new job.  We […]

The rug business turned out to be a little more difficult than anticipated. My fixer was a ghost. The wholesaler I was supposed to sell to in Boston cancelled his order.  I was stuck in Dar-el-Beida with 800 rugs and nothing to do with them. And it was going to be such a wonderful summer. […]

All told, Daryl, Tracey’s ex-boyfriend, wasn’t such a bad guy.  Sure, he had a crippling jealous streak in him. Sure, he stalked me all the way to Madrid, hid in my closet, attacked me, and subsequently dragged me by my ankles all the way to Chueca, where he offered 50 euros to any man who […]