mailboxKnox, me and my boyfriend are in a long distance relationship of one and a half years, and I can’t shake the feeling that he’s cheating on me. What’s worse, he’s applying for grad schools and I’m waiting to see where he gets in, and then we’re going to decide where I’m going to follow him to move, and I know it will work out once we’re in the same city, but I’m not sure if we can hold out. Do you have any advice?

Continue reading ‘ask Knox: long distance is the wrong distance’



I have no comment on this song. Just listen and try not to let it make you too sad.


knoxSo Margot didn’t or couldn’t want me and I knew I had to get over her. But I couldn’t help but submerge myself in guilty feelings of unrequited love a little bit longer. A couple weeks after her final rejection I left a long message on her voicemail.

“Hey Margot; it’s me again. Sorry to bug you.  I know you’re probably freaked out by the calls and I want you to know I understand. It took me a while to understand. I didn’t show up to work a couple times because I was so torn up, which, I know, is crazy, because we don’t know each other that well.

margot5“It’s weird. But I just feel like I need closure with you, which is unlike me.  Frankly, I haven’t really been myself since I met you. So anyways, I’ve been camping out on the coast for a couple days. Drinking a lot, but it’s given me a fair degree of clarity. I dunno, I guess I was just feeling trapped in my old relationship, and I met you, and you’re such a rare person. It just shook me.

“But listen.  I get that it’s not going to work. I know it was a mistake for you to go home with me. It bums me out, Margot, but it’s OK. And guess I just had to call and say that. It’s going to be OK. And—“

Right then, I was cut off by her answering machine. I thought about calling back to finish the sentence, but realized I’d said what I needed to.

Continue reading ‘Margot, the elusive (part 5)’


knoxMargot’s words of rejection following breakfast sank beneath my skin like a hot cattle brand, but I still tried to play them off all cool and calm.

“I admire your candor, Margot, but you didn’t quite answer my question. I didn’t ask if you wanted me. I asked what you wanted to do with the rest of the afternoon.”

margot4“I’m sorry?” Her brow furrowed, a puzzled look set in across her face.  I had clearly confused her, which had been my intention. By doing so I was able to buy myself some more time.

“No, please don’t be sorry it’s quite alright.”

“That’s not what I –“

“This weather,” I grabbed Margot by both her hands, “It’s fucking glorious! Look!”

Together we both turned our heads, and her hands began to relax in mine. They were warm and soft, slightly damp.

Continue reading ‘Margot, the elusive (part 4)’


knoxWaking next to Margot in her bed I couldn’t describe the feeling – something between shock and schoolboy glee. Like winning the lottery. It’s rare when you roll over to see a girl’s messed up hair and smeared mascara, pillow lines in her face, feeling that awful pounding in your stomach from a night of drinking, and all you can think is: oh-fucking-yes.

Margot3

It’s odd, but most of the time, when there’s a girl so beautiful, intelligent, confident and interesting, I act like a bumbling moron who can’t even conjugate verbs. But every so often there’s a woman like Margot who inspires me to say all the right things at the right times; to hold my liquor; to write epic love letters that are smart and funny – hinting at an endless reservoir of deep feelings and sentimentality – and even romantic comedy-esque silly bullshit that you won’t voice because you have some modicum of taste and restraint and sensibility. This is what happened with Margot. She made me perform at 110 percent.

I had run into her the night before at an open mic and we got to chatting about how much we both hated most acoustic guitar music. She asked me if I played. I said yes. Then she wandered off to talk with some friends. Just as I was about to leave dejectedly, the MC said, “And next on our list, we have Knox Dupree.”

Continue reading ‘Margot, the elusive (part 3)’


knoxI waited outside Margot’s work a couple times, but she wouldn’t speak to me. I knew I was drifting into restraining order territory, so I backed off. I’d given up a good relationship of a year to chase after Margot, but my pursuit had been complicated by the fact that my ex was Margot’s old roommate from Oberlin. They still talked, I guess.

margot2So I waited it out, pondering why I liked Margot so much – after just one evening of conversation. There was something about the way she carried herself. It reminded me of women I’d known at a younger age, when we were all still curious and optimistic. You’d explain your ideas to her and she’d listen intently, staring you in the eye. As she began to comprehend your point, a slight smile would creep across her face.

I made her a mixtape but didn’t have the nerve to send it. I walked through the neighborhood where she worked but never saw her. I imagined what our relationship might be like, crazy, project-based, and quietly sexy. Waking up Monday mornings and each of us calling in sick to work, so that we could lay in bed with each other all day, smoking grass and listening to old soul records.
Continue reading ‘Margot, the elusive (part 2)’


knoxMy girlfriend took me to see Margot, a friend of hers, perform in a one-act at an old Supercuts-turned-experimental-theater in North Portland. I’d never met Margot before, but I could tell my girlfriend didn’t like her very much, even though they were ostensibly good friends. It was something about my girlfriend’s tone as she reported news of dear Margot:

Margot - photo by Todd Gehman (http://www.flickr.com/people/pugetive/) used under CC License“My friend Margot is going to Barcelona in a couple of weeks, which is so dumb, because it’s not even that nice there this time of year.”

“Margot once threw a dress-as-your-favorite-song party, but didn’t even dress up herself, because she said she realized it was ‘too heady a theme.’”

“God, she’s such a cunt.”

The play was about a stuntman who became terrified of leaving his house to go to work. Margot played his wife, who every morning fights and fights with the guy, telling him to go do his damn job. It would have better if there were some actual stunts, but it was a fine production.

At the after party I found out why my girlfriend felt competitive with Margot. You see, Margot was just better. She had better posture. She was more impulsive. She had better luck. And as we chatted over Trader Joe’s wine at the director’s apartment, I realized I actually liked Margot better than my girlfriend.

It was a revelation. I didn’t even feel guilty about it – just surprised. We had a good time that night, the three of us, staying up until 4 a.m. As Margot shared stories and ideas, I listened closely and thought in the back of my mind, “Wow, I am really dating last year’s model.”
Continue reading ‘Margot, the elusive (part 1)’


mailboxHey Knox,

I’ve been dating this girl for about seven months and I’m really into her.  I think she’s into me and we’ve both implied that we’d like to try to get deeper into our relationship. The trouble is, she’s way more experienced than I am and I can’t get it out of my head. I’ve only had one serious girlfriend in the past and haven’t had too many other women. Meanwhile my girl has slept with 30 or 40 guys. Every time we bump into a guy she knows I can’t shake the voice in the back of my head asking, ‘Did he fuck her? Was it better? Would she do it again?’

Subconsciously, I think it’s caused a lot of arguments, and I know that my girl isn’t cheating on me, but I just can’t shake the jealousy. What should I do?

Continue reading ‘ask Knox: experience’


mailboxI recently discovered your blog through a friend. My boyfriend and I broke up this week (yes, it took a whole week to actually end) after 6 wonderful months together. We love and care about each other so much. The problem is that he has a highly stressful job that has required 80-hour work weeks the past few weeks – he’s a major player in most of the front page stories you see in the WSJ and NYT. I work in the same financial sphere, so I understand his stress and the importance of what he does. We decided that being in a relationship is just not conducive to his crazy work schedule. The break-up was very sad and very amicable. We really want to stay close friends and talk frequently. I don’t see a problem with this at all since we obviously want to stay main characters in each other’s lives, and who knows what will happen down the road. Maybe we will date again. After all, we were both thinking long-term here. My mother completely disagrees with me – she thinks I should cease contact and move on. My friends are somewhere in the middle. We each have no interest in pursuing other people – his work just became a major stress for us both.

Not being able to talk or be friends would almost be devastating – we are just great together and have become such big parts of each other’s lives. But I’m interested in a second, impartial opinion – I look forward to your thoughts.


Continue reading ‘ask Knox: high pressure breakups’


This piece was sent in by Brendan Byrne, creator of theorphan.org.  The quote, “The Orphan is incomplete, unpublishable, moloch-less, disrespected, bizarre and roundly rejected.”  Though based out of New York City, Brendan does a fair amount of traveling, as illustrated in the story below.  His stories have been featured on flurb.net, and he has number of novels in the works. The story below is a sad, somewhat eerie account of both a woman and a city.  As I’ve said before, there’s something irresistible about comparing the twoBut I’m not sure “romantic” would be the word I’d use to illustrate this tale; it’s more haunting – a story about loss, decay and giving up.  Certainly a heartbreaker.  I hope you all enjoy it as much as I do.

nezaThere were cripples in the street.  Old men, young women, university students: they had frozen knees, stiff gaits, double canes.  I was in Vienna, in Europe in general, to get away from cripples, away from death.  My father, who suffered from CP, had finally committed suicide at the age of 56, leaving my mother with medical bills and a long political-historical treatise, which will probably never be published.  I’d spent the last few months hanging out with him in Providence where he was recovering from serious hospitalization.  I didn’t blame the old man in the slightest.  I’d just had enough of cripples for a while.

But, of course, it was May.  Paris-Madrid-London-Berlin-Prague, all on hostel cots, with bloodshot eyes, mine and others, none of them suited me.  Too cheery, too lovely, too wonderful.  Too full of life.

Vienna, however, was different.  In the hot spring sun, everyone still wore black.  Their faces were pinched, their paintings were fierce and fucked-up, they all smoked, even the infants.  Even better, they were polite to a fault, which was good because I wasn’t looking for human interaction.  The city was beautiful, but its soul was ugly.  It suited me perfectly.

Continue reading ‘Death in Vienna’


knoxOne thing I’ve realized since beginning the Heartbroke Daily is that it’s impossible to compare the different times I’ve had my heartbroken to one another. You can’t say which time hurt more because they always seem to find a different part of your heart to wedge the pain into. That being said, revisiting Connie Converse this morning got me thinking that there’s a special place in my tattered heart for the women who have left without a trace. Something about the lack of closure really hits you in a different way than, say, having it end in an explosive argument or with a well-crafted I-never-want-to-see-you-again letter. Because with any real relationship, the woman becomes a part of you (well, for me, at least) and when they vanish with no warning, it’s like getting sideswiped.

So with that in mind I thought I’d share some of the best (or are they the worst?) stories of women who have disappeared on me. It also occurs to me that some of you might disagree. Some might rather have a loved one simply go, without knowing where or why. That it might make it easier for you to cope if you don’t know what happened. Please share your thoughts in the comments, because I’m curious to know what you might think.

Laila, the phantom itch

lailaThe cold, empty side of the bed. The twisted sheets. Laila always insisted that I make her bed each morning.  She had a 9 to 5 at the time and I just barely slid by with my laptop and a few gimmicks.  So I got to sleep in.

“Just lock the door behind you,” she’d say.  “And make my bed; you thrash like crazy—it’s like you’re trying to tie bowler knots with the sheets.”

“That’s only when you’re not in bed with me,” I’d say.

And it was true.  In my sleep, after my body sensed she was no longer there, I’d thrash about in the depths of my subconscious, searching for Laila.

read the rest of ‘Laila’

Laura, the confidence artist

Laura, the confidence artistKansas City, I wind up playing blackjack next to Laura at an underground casino. I was up about a grand, because I know the game and the limits of my own luck. She was up twice that, because she was counting cards. When I realized what she was doing, I leaned in and whispered, “Listen dollface, when the house gets wise to your math skills, they’re gonna do more then ask for their money back.” She played if off cool – lost the next couple of games on purpose, then headed to the teller to cash out.

A couple of days later, I ran into her at my hotel bar, waiting for some out-of-town businessman to offer her a drink.

read the rest of ‘Laura’

Continue reading ‘digression: disappearing day’



connie-guitarIn August of 1974 Elizabeth “Connie” Converse disappeared. She wrote a handful of goodbye letters to friends and family and packed most of her belongings into her Volkswagen. In her brother’s garage she left behind a haunting body of recorded music that would remain virtually unheard for the next 35 years. She also left a filing cabinet full of photos, tapes, journals and letters. She drove off and was neither seen nor heard from again. No further record of Connie’s life or death exists. She simply vanished.

In 2004, two longtime friends and audio engineers, Daniel Dzula and David Herman heard one of Connie’s songs broadcast on David Garland’s Spinning on Air. Afterward they got in touch with Connie’s remaining friends and family, heard more of her music, and learned more of her mysterious story. In 2008 they formed Lau derette Recordings to ensure that Connie’s music would be preserved, and that the quiet, melancholy beauty of her songs could be recognized.

Continue reading ‘heartbroke audio: One by One, by Connie Converse (1954)’


AA Meetings. Home Depot. The Episcopalian Church. Good God, where else?

During times of great scarcity, want, and desperation I have found myself turning to the most unusual places to pick up members of the opposite sex. Never, though, have I had the slightest inkling to join a book group. And after reading this story from a good friend and former colleague of mine, I don’t plan to do so anytime soon.

jane-austenSingle women looking for a man read Jane Austen novels.  That’s why I joined Jane Austen book groups.  I thought they would be a happy hunting ground.

Having recently gone through a particularly traumatic and heartbreaking separation from a woman who, at the time, I thought was my one and only true love, I signed on to Austen mania.  And it worked.  I met Janine at one discussion group.  She had long, raven hair, and I was immediately attracted to her when I discovered “Mansfield Park” was her favorite novel.  She had a sharp, sarcastic wit, and, like Miss Cawley and Becky Sharpe, we used to go for drinks after book club meetings and “abuse the company.”  Pretty soon we were dating.

Andrea, Denise and Charlotte were also in our book group.  All three of them were as mean as junkyard dogs.  Their favorite Austen quote was, “Elinor agreed with everything he said, because she didn’t believe he deserved the compliment of rational opposition.”  Their favorite novel was “Emma,” but they were no matchmakers.  Instead, they obsessed about how to break Janine and me apart.

Continue reading ‘Happy Hunting Grounds’


lovers1Here’s a band called The Lovers that, perhaps ironically, broke up.  They moved to LA, separately.  The drummer went around the bend and ended up in Portland.  Had something to do with a girl, I recall.  But for a brief time they developed a loyal following in Eugene, OR.  The lead singer, Aja, worked at a coffee cart on campus and she’d hook me up for free to keep me talking to her when business was slow.  She was always such a chatter box. By the time I’d leave to walk home I was cracked out on caffeine, my mind reeling from Aja’s stories and her massive, brown, almond-shaped eyes. Together we’d get drunk and rowdy from time to time – well, most of the time.

Anyway, this song, “Infection,” has helped me through a number of lower moments over the last five or six years.  It bleeds of drama, pills, booze, love and the bittersweetness of being gifted/afflicted with being young, drunk, talented, broke and beautiful.  Every time I hear it, I see a blue and gold sun setting as the last of the cheap red wine dries in that little ring at the bottom of a glass. I’m too young and I lost my ID, so I can’t buy more drink, so I just dream of a girl 3,000 miles away, more of an idea than a real person.


You can hear more of The Lovers here.


mailbox1

Dear Knox,

I read The Heartbroke Daily almost every day, though mostly out of utter disbelief. You’re a misogynist. You’re pathological. You’re more or less a failure. I also figure that on account of you living hard and drinking hard for so many years you must be rather unattractive these days (which would explain why you’ve never once posted a picture of yourself on your site).

Are you seeing anyone these days? How can anyone even stand you?

To answer your last question first, no I’m not seeing anyone at the moment. I am currently in the process of separating from my wife and have tried to avoid further romantic entanglements until it is over. I have never wanted to turn this project into a so-called dating blog where I detail my life in real time. Because the driving force behind the site is about heartbreak, it seems like we all have more perspective on our lovesickness with distance.

Now, I will agree that I am in many ways a failure and even pathological, but I take issue with your calling me a misogynist. I don’t hate women or girls. As we began our divorce, my wife yelled, “Dammit Knox, I don’t get it – how can you love women so much yet hate yourself?” So, if anything, I’d be a self-loathing misanthrope – but only on my really bad days.

As far as my good looks go, I never was much of an Adonis even when I was young, before getting my ass handed to me in a number of boxing matches and bar brawls; before falling into the roller coaster ride of self destruction and obnoxiously healthy asceticism. I’ve been told I had an interesting look before, but no one has ever described me as much more than that. Believe me, I’m as confused as you are.

What can I say? Life is not fair. Whatever the case, I’m so glad to hear that you enjoy reading the blog.


Cinco de Mayo

05May09

knox2I have little interest in holidays.  While I do enjoy having a legitimate excuse to get drunk and disorderly, I don’t necessarily like it when everyone else has license.  I mean, most people aren’t very good at drinking.  St. Patrick’s Day and New Year’s Eve are like amateur night across the country.  Silly, stupid hats, green drinks, frat boys and the women who love them—all gallivanting about the city, throwing up all over the sidewalk.

cinco2Christmas is less like this, of course, unless you consider my father.  One would think he’d be better at drinking after all those years, but he still always managed to drink too many complimentary drinks, drop a grand on roulette and pass out on the floor of the hotel room with his clothes on.  Thanksgiving, he’d sit at our aunt’s table and just mumble about my mom, who only left her piano behind.

Continue reading ‘Cinco de Mayo’


knox1Cass met me during a calm period in my life. Settled into a lecturer’s position at the city college, I was still drinking, but not excessively. Writing more consistently. Feeling stable. Cass, who’d experienced a wild life trajectory as well (travel, addiction, success, burnout, rehab, repeat) was going through a similar phase.

cass2On our first night out, when it wasn’t clear whether or not it was a date, she summed up our matching mindstates rather nicely. “After realizing I had to keep getting further out on a limb to affect on my happiness, I decided it was just easier to keep it cool.”

“Yeah, I agree, but in my experience, you eventually snap out of it and chase the remnants of your youth harder than ever.”

She smiled.  “Yeah, maybe.”

The best word to describe our relationship was cozy. We often cooked meals, either in my modest studio, or hers. Occasionally we ventured out to my favorite dive bar for aging hipsters, but more often than not, we headed towards the local independent video store, for a quiet night in.
Continue reading ‘Cass, the cineaste’


knoxI won her in a poker game after getting out of jail – a 1985 Nissan pickup truck, faded yellow, full of dents, a disintegrating interior, a busted radio and no turn indicators. Certainly, she didn’t look like much, but that was OK.  Though I am a lover of beauty, form tends not to trump function.  And she never let me down.  Aside from minor repairs and oil changes (all of which I did myself), she didn’t cost me a dime.  Together we crossed the country six times, through 45 states.  To keep from losing my mind, I wired a stereo into the cigarette lighter, and when the music got old, I’d speak to her in Spanish and sing country songs.
07venablenissonpickup_s

It’s never been my nature to get attached to material things, and I’ve never respected fancy cars or the people who drive them.  I’m not a ‘car guy.’  But there was something different about my truck.  I mean, she wasn’t a material thing per se; no…she was my horse. Every time I went over a bump I deemed too heavy, I tapped the dash with empathy, as if to say, “I’m sorry.”
Continue reading ‘Surefoot, my truck’


Cadence WeaponGot sent this by my webmaster, Henry, who thought we need to diversify our genres for heartbroke audio a bit more.

Hey Knox,

I’ve been thinking a lot about the heartbroke audio section and I wanted to try and get some hip-hop songs up there, and thought this song by Edmonton-based hipster-rapper Cadence Weapon might be a good place to start.

See, the whole song plays out as conversation between him and his tattoo artist. He begins by talking about the tattoo, but slowly transitions to rapping about his ex-girlfriend, who may or may not be the impetus behind him getting a tattoo, at one point telling the artist, “you’re a cheaper shrink and you put something on me”. I just love songs that can hold so much duality, and it highlights the fact that reason we tell ourselves we’re doing something (i.e. getting a tattoo) might not be the actual reason.

I also love the coda he says at the end: “So it actually does hurt in the end, but I’m done writing songs about her, you know what I mean? Why would you obsess over a girl who doesn’t like you? I mean, some people make careers over stuff like that…”

What do you think, Knox?

I think I like it, Hank. You can hear more of Cadence Weapon’s music here.



knox6I can imagine her getting on the plane to meet me in Rome. She strikes up a conversation with the man sitting next to her. Smiling, listening, twisting a finger through her cropped, blond hair. Realizing that she had more in common with the stranger than she did with me. No 12-year age difference, both studying English at the same university. Maybe they even share the same sense of goofy humor I could only pretend to relate to. Maybe that’s what happened.

lucyLucy, a student at USC, worked at a café near the warehouse-office I shared with a few other freelance creative-types. She was a bubbly university student, and I was a successful older man pursuing her with all the instruments my relative wealth allowed. Expensive meals at yuppie establishments and gifts of hard-to-find records or tasteful artworks. After six months, as I was headed to a conference in Rome, I invited Lucy to come meet me. “Finally, another stamp on my passport, Knox!” she said, so excited by the offer, so enamored with her generous, slightly mysterious older man.
Continue reading ‘Lucy, the no show’



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