4 | The Hipster: Tenth Avenue Freeze-Out

A few days before Thanksgiving, The Hipster broke up with me. Hahaha. Of course he did.

Unsurprisingly — to literally everyone, including myself — he balked at the breakneck speed at which he had jumped out of one relationship and into another. We had gone out for pizza (that he never respected the sanctity of pizza really should have been the dealbreaker) and afterward, sitting on his couch, he had become noticeably withdrawn. It was a lot of blah blah and then some yadda yadda, a little more blah blah, the sum total of which was: you’re great, this is great, I want to be with you, I can’t be with you. Cool cool cool.

I couldn’t face going home, pathetically deflated and alone, so I spent the night there. Just thinking back on how emotionally excruciating that sleepless night was, I’m sad for my 22 year old self. I lay awake, looking through the breaks in his shitty venetian blinds — the ones that came with the apartment and he had never bothered to replace — staring at the crystalline curves and sunbursts of the Chrysler Building. (Insert here: trite Sex and the City metaphor about how He was My Chrysler building. Ugh, anyway.) Saying goodbye the next morning wasn’t awkward at all. Sure. My despondence was almost less about the actual heartbreak, and more about being daunted about how boring my life was about to get. I was like too bummed to even cry.

In the following weeks we saw each other regularly at our grad school classes. It was Torture. I mean, for me. Pretty sure he was already banging dating other chicks. I pretended to be cool with being “just friends” (or whatever), but, in truth, I really was heartbroken. I’d see him and his delicious butt in those skinny jeans and my heart would leap into my throat. While I was supposed to be learning about differentiation, I’d just spend class thinking about all the Best Nights Ever that I was surely SURELY missing out on, actively putting my energy toward not (ugh, god, vom) thinking about whatever much cooler than me heiress he was surely SURELY falling in love with.

And then, about three weeks after we broke up, we got back together. Hahaha. Of course we did.

We celebrated the reunification of this psychotic chemical attraction love for the ages by taking off to California the day after Christmas. We road tripped from San Diego to San Francisco over the course of a week, visiting friends of his, friends of mine, making a detour in Tijuana (haha sure sure, v smart and completely sane idea for the two of us) and generally just running amok on a different coast. For reasons that will hopefully (hopefully!) make sense later, I’m going to save the story of this trip for The End, because, well, it would end up marking The End for us.

So anyway, when we got back from California, it was a New Year and a New Us. Lololol jk jk, same old us, same old bullshit. Even after we became a (somewhat? maybe?) real couple, much of the time we spent together that winter was basically one big dare. It was very hard for us to Slow Down. It didn’t matter if it was like a Tuesday and we were both secretly Exhausted. If either one us intimated that maybe we did want to possibly check out That Thing or That New Place, the other put on their big kid skinny jeans pants, laced up the converse and grabbed the bourbon. Neither of us would admit to being normal human adults who just wanted to go to bed at a reasonable hour the weak link. Before FOMO and YOLO were cultural touchstones emptily bemoaned in hashtags and gifs, we were the actual human avatars of those acronyms.

One Friday, however, I got to his place after work and he told me that he didn’t care, he was tired and beat up and didn’t want to go out: he told me he was putting his beautiful brown foot (possibly my words and not his, who’s to say, really) down and we were Staying In. This was Unprecedented. However, I readily agreed, because for me, the benefits were twofold. One, and most importantly, I got him all to myself. Two, that weekend one of those polar arctic something-ageddon vortex snaps was happening and it like hurt to blink if you were outside. So, we over-tipped our overworked delivery people and hunkered down. It was intimate. It was slothful. It was glorious.

On Saturday night one of his friends came over with red wine and dominoes — the game, not the “pizza,” how dare you. The three of us played for hours, shunning the sub-zero weather and The Scene. Not to sound, like, a thousand years old but the standout memory from that night is simply how simple it was. We definitely had music on, something like St Germain or Ali Farka Touré, but that was it. There was nary a Boomerang of a falling domino to be found. I am the queen of The ‘Rang, I’ll readily admit it, but it was easier to be anonymous then, easier to disconnect if you wanted to. All these years later I remember being so happy and having so much fun in the minimalism of that night.

Cut to: Sunday evening. By that time the sparkling novelty of our insanity-free Norman Rockwell wholesomeness had worn off and we were officially Stir Crazy. We were, after all, 20-somethings and certified lunatics. Thankfully, someone in his crew called to say they were going out, and we were saved, from our sloth and ourselves. I already had my coat on by the time he replied to his friends to tell them we’d meet up. The Hipster’s friends were (still are) a super tight Crew, and they were forever doing something on Sunday nights so as to stave off “Sunday scaries” (again, before that was even a thing). Ice-ocalypse or shine, they could always be counted on for a good showing and a bit of mayhem.

We met everyone at Ace Bar, which effing miraculously still exists, and it was absolutely dead. So, we took over the tucked-away back part of the bar, draping ourselves over booths and readying the pool tables. I was tasked with heading to the bar to pick out some tattered board game or another, again attempting to add that whimsical touch of wholesomeness to our alcoholism impromptu Sunday cocktailing. Turns out, the only other degenerates brave souls who felt the sirens’ call of cheap booze on a frigid Sunday were two older men posted up at the end of the bar. One had white hair and looked like an extra from The Sopranos. The other was slack-jawed and paunchy, wearing a trench coat and looked a little bit like a cartoon villain. Naturally Paulie Walnuts and Boo Radley start to chat me up.

Now, I say Naturally, not because I’m gorgeous conceited but because this is just what happens to young girls in bars, especially in the vicinity of older men. More often than not these flirtations are unsolicited, uncomfortable and it feels like you need Seal Team 6 to run a special black ops extraction mission in order to get you out of the haltingly polite conversation you feel contractually obliged to have when you really want to just be back with your friends. Ugh, anyway. Despite my exaggerated aloofness and intense concentration focused on picking out the perfect board game that none of us would actually play, Boo Radley really kept trying to buy me a drink. Now, I’ve accepted many a drink in my eon, I mean, day. However, I’ve always done so with a bit of w(e)ariness because a. these oh-so-generously offered drinks are never free; they cost your soul time and patience and b. like, OMG old man in trench coat, you are literally the exact caricature of who I was warned about talking to when I was 12 and in D.A.R.E.

As broke as I was (was? am? always, constantly, whyyy), I didn’t feel right taking the drink and just bouncing to go back to my boyfriend and friends, so I declined and managed to extricate myself from the conversation, fake smile plastered onto my face, stupid board game under my arm. As I sat down in the booth and started tell The Hipster my Get a Load of This, These Guys at the Bar story, Paulie Walnuts and Stranger Danger sauntered over to the pool tables. I elbowed The Hipster to be like See! That’s the Guy, but he wasn’t paying attention because at the exact same time someone else at the table was stealing my sanctimonious thunder, saying: Holy shit it’s Steve Van Zandt.

Oh hahaha lololol neverrr mindddd old homeless man hitting on me was v famous rock star and television actor false alarm it’s kewl. Being the only people in the bar, we quickly became fast friends. And, so, on a frigid Sunday night we played pool and shot the shit with the rockstar and the consigliere — both of whom, incidentally, turned out to be very nice.

3 | The Hipster: Fall

The beginning of our relationship was all fits and starts. We almost called it about 17 times during those first few weeks. I mean, I can’t imagine why. Some business about him not really being ready to emotionally commit to someone, long term roommate something something red flag whatever whatever. Every few days, it felt like, we’d agree to “slow things down” and then Friday would be its minxy saucy self and all bets would be off. At this stage in our lives (me, him, BF, Everyone) we were all always Out. There wasn’t ever any possibility that one would call the other to be all like HeyWhereYouAt and someone would answer Nah, man, sorry, I’m in for the night. Lololol. Home. Like sane people. Right. So because of this and because of the absurdly awful auspicious timing of this burgeoning battle royale relationship, at first, The Hipster and I never actually Made Plans. (See aforementioned Green Light near-fiasco.)

I tried to pretend I was like totally cool like super evolved whatevs I’m chill. He tried to pretend he was totally single like you are def not my gf I am toats single ok. So, we’d collectively pretend that maybe sure we’d all meet up later at some point cool yeah give me a call or like we’ll run into each other or… but the reality was, we just wanted to be together by the end of the night. So whether it was 9:30 or three (three!) in the morning, we’d weave our way toward whatever drinkery the other was at. Him: somewhere impossibly cool with models and bottles, where I totally TOTALLY fit in wearing my ripped Johnny Cash t-shirt. Me: some hepatitis den where I could drink cheap bourbon and dance my leg-warmered heart out. I lived (lived) for the nights when I’d be out with friends and all of a sudden look up to see him dancing toward me, huge smile on his face. The rest of the bar would fade away and it was just him and I in our Converse, skanking to Madness. Those moments were magic. And, so, even though, as a Unit, we made No Sense, those moments, those nights, quickly gained traction, and it was with enviable naivete, that, we Jumped.

For our First Official Date, he invited me over to his place. He wanted to cook me dinner. You may be thinking Swoon! Romance! Nope! I was having a low-grade panic attack. For a somewhat (god, ok, fiiinne: very) picky eater, this scenario is A Nightmare. The prospect of having to tell the man you just started dating, who you adore — and who you are dying to impress with your coolness — that whatever he’s making or has made makes you want to vom is just, god, no, dating horror. When he told me he was going with Italian, I exhaled slightly, because barring like tripe or scungilli (but seriously, why would you eat those) anyone can hang with Italian food. Plus there’s pretty much always red wine involved soooo we good, we good.

Thus, on a Friday evening I found myself on the 40th floor of a luxury apartment building in Murray Hill, not believing that I was actually in his kitchen, watching him pour me a glass of red wine and that we were on a Date. As he made a show of prepping things, he told me the story of how he had gone down to the grocery store Little Italy to buy fresh pasta. Wandering the streets, looking for the perfect spot, he met a stooped old Italian nonna who didn’t exist just happened to be standing at the entry to the deli case her cold water flat. She beckoned him upstairs, where she handed him a package of Butoni just happened to have batches of fresh ravioli that she sold only to people who proved their worthiness with a story deserving of the ravioli. So he told her all about the girl he had just met who he wanted to impress; about her blue collar roots and altruistic nature and —

Lololol. Wut. Stahhppp. Just boil the water already, Scorsese.

Even in my heart-eyed-emoji state, I was not completely blind to the apocryphal nature of his story-telling. It was epic. It was what drew people to him. It was what made his eyes light up and incited that throaty chuckle to come rumbling up from his toes. It made every night seem like it had the potential to be The Best Night Ever. It was also, eventually, our undoing. But the thing was, he actually did enough crazy shit, enough of the swoony grand gesture crap, to keep you investing, wanting to believe, in the Legend. E.g.: One night, at a burger joint near his apartment, so wrapped up in the conversation was I that I didn’t realize I had slowly leaned closer and closer to him — over the table, over my dwindling plate of fries. At one point I sat back and he just looked at me and laughed: I had ketchup all over my, shall we call it, bosom. I tried to play it off and laugh, but I was mortified by my own clumsiness. He simply looked at me, still laughing, shrugged and wiped a streak of ketchup across the chest of his white shirt. In those sparkling moments, etched so clearly in my memory, the stories — the good stories — came to life. And, those moments sustained some of the truly shitastic garbage that went down.

Because, duh, it was not all Matthew McConnaughey rom-com bliss. At the beginning, things were messy. Halloween weekend we were supposed to meet up. (Kill Bill theme: I was dressed as Gogo and BF was O-Ren Ishii. We nailed it, obvs.) After not hearing from him once (ONCE) all weekend, he texted me Monday to tell me that he “forgot” his phone “at school” for the ENTIRE WEEKEND. I mean really, go eff yourself with that one. Now, lest you think I’m a total schmuck, of course — of course — I knew this was 100% Absolute Bullshit. And it wasn’t that I didn’t care or wasn’t hurt, rather, I was 22 and had yet to experience the I Can’t Unsee This kind of emotional scarring that catalyzes self-preservation. (Don’t worry, we’ll get to that one later. That’s gonna be a REAL fun one, you guys. Ugh, anyway.) So, as all people in love do at some point in their lives, I explained it away reassuring myself it was fiiiinnnneeee and it was all good, right? (RIGHT?)

Oh, but wait. Then there was the time that I’d summarize as: We all got pizza. All Hell Broke Loose. After dancing our faces off at Niagara one night, The Hipster, BF, some college friends of ours and I went next door to eat some pizza, as you do. I was amidst hostile negotiations with one lactose intolerant friend who was adamantly insisting we had not allowed her to eat pizza. While I was frantically assuring her she had already eaten her slice (seriously, she scarfed it, record time), I noticed a disturbance in the force over toward the curb —  and The Hipster stalking off up Avenue A. Pulling my lactose/memory-challenged friend away from the pizzeria and toward the other two, I felt panicky. This was not an unfamiliar feeling, clearly. The first couple months of our dating I was always convinced the bubble would burst and that it would all end.

Surrounded by throngs of drunken revelers, my friends told me how a girl had walked up to them, she and The Hipster had had an awkward conversation, and upon her leaving, he turned to them, threw his pizza on the sidewalk (fucking blasphemy) and stormed off. One guess who it was. Ding, ding. Ex-Roommate. The drunken, emotional back and forth, (his apology, my martyrdom, his guilt, my reassurance, his baggage, blah blah) that followed is unnecessary to recount in granular detail. All I know is that at my heart tugged that small whisper of Knowing; that he wasn’t ready and I had no idea what I was getting myself into. Still, as The Hipster and I hailed a cab (and Lactose Intolerant pushed BF into a bodega flower stand and then took off running), we committed our bourbon-soaked selves to this enterprise.

Dating for us was less about activities per se, and more just various beverages in an array of locales. Over beers, at Chumley’s, we shared stories of family. His: Indian and strict. Mine: Irish and a little crazy. We recounted high school. Him: sneaking into the city to party at Limelight. Me: s’mores and mooning over the guy who worked at Starbucks. (So, samesies, really.) Over coconut martinis, at Pravda, we made travel plans. Over bespoke cocktails, at Milk and Honey, we discussed literature. After first impressing me by pulling out the business card with the unlisted number for the members-only bar, he then tried to also impress me with his knowledge of Hemingway and Fitzgerald. As I sipped my custom drink, I remember watching him get a little annoyed that I could not only hang in a conversation about the Lost Generation, but that I could best him on a few points. I enjoyed watching him squirm, and finally he conceded that what made me simultaneously terrifying and attractive was that I just might be completely legit.

One day we found ourselves at McSorley’s, telling our September 11th stories. He hadn’t wanted to go in. Right after the attacks, he said, he had been with friends and the very blue collar, very Irish bouncers wouldn’t let him in. Staten Island native, 2nd generation Irish, daughter of a firefighter, niece of three cops, I’m sure, even though he’d never actually say it, I represented to The Hipster exactly the profile of people who might call him — had called him — “towel head” or “sand n—ger” or “camel jockey” when he walked down the street. Appearance alone couldn’t tell you he was a kid from Long Island who liked The Cure, drank like a fish and thought the only God that existed was Nabokov. (I mean those jeans were real tight though, so that really should have been some kind of tip-off.) New York City in 2003 was still very much a post-September 11th city. I think we always will be, but then it was still very palpable. The summer I moved home it had not yet been two full years since the terrorist attacks ripped our hearts out on that temperate Tuesday morning. Our commutes were still messed up, purple and black bunting still hung from firehouses — we were still scared. Our experiences of that day were very different, but there we sat over our lights and darks and found that it didn’t truly matter. We both harbored an unconditional love for this city, one that largely informed our own fledgling love affair.

My relationship with The Hipster was far from perfect, but man was it fun. It was messy and raucous, genuine and manic. We were in constant pursuit of, well, everything. Everything that love offered, everything that New York offered. And that fall while I fell in love with The Hipster, I also learned how to love this new version of my city, one that was a little broken, very scarred and gorgeously imperfect.

2 | The Hipster: The Kiss

The first time we kissed, I was barefoot. In Greenwich Village. In the late-summer. This is: Disgusting. However, I could have been standing in a puddle of bubonic plague and giardia for all I cared; all I knew was that he had me pressed up against the side of a building (It was NYU. It was classy, ok.) and he was finally FINALLY kissing me.

That night had begun as all nights during that era did: Best Friend and I eating Thai food and getting ready at her law school dorm. Getting ready involved concocting horrible outfits, me obsessing over whether or not we’d end up Meeting Up with The Hipster, and drinking — exclusively — Diet Coke with vanilla vodka (It was Grey Goose. It was classy, ok.) I probably made us listen to a mix CD I had made that went from Cafe Tacvba to The Clash to like 112, or something equally schizophrenic cultured. Sometimes, before we headed out and she headed to bed, we’d ask her poor introverted roommate (soz we were lunatics, Ellen, our bad) to take pictures of using an, ahem, camera — the pictures from which we actually printed out. Like actually took film to an actual drug store. Wild.

On the night when the stars aligned, I was wearing an “outfit” in the genre I like to think I pioneered myself: punk rock hoodrat. The foundation around which this masterpiece was built, was a white t-shirt, men’s, that BF and I had ripped apart, cut up, and tied TIED back together. There may or may not have been a ribbon involved. IDK. I wore this off-the-shoulder number, with its “sexy” peek-a-boo holes down the side seams, over a purple bra, paired with jeans and a pair of her heels that I proceeded to baby-deer in all night. My hair was in a side-part, slicked back ponytail, accented with a fake flower, and very large gold hoop earrings. In complete aesthetic harmony, the pièce de résistance was my studded belt. Oh, wait, did I mention the lip liner? Dark lip liner, silver lip gloss, natch. BF was wearing a pink mesh MESH muscle tank that she had “like picked up in Europe” accented by a silver Tiffany’s choker and super scrunchy gelled hair. So, obvs, we looked super schizophrenic hot.

I don’t truly remember the set-up, but I’m sure The Hipster and I had made some vague too cool non-committal whatever it’s fine I’m breezy plan to “meet up at some point.” He was, after all, now Single. BF and I decided it would, of course, be better to wait until later to reach out to him so as to be all stone cold fox about it. Sure, sure. I just needed to be drunk enough to have the balls, let’s be honest.

Back then every Night Out felt like possibility and adventure and Ohhh what’s going to happen? Where will we end up? Who will meet? (As opposed to now where it’s all like Who will we meet? Us, the people we came out with, no new friends, clearly. Where will we end up? Home, in bed, at a reasonable hour because I want to go to the gym in the morning, obvs.) So we left her roommate in peace and set out for god knows what. I don’t remember all the stops on our tear that night, but I do remember it was after dancing at Parkside Lounge that we decided, for our respective reasons (me: antsy AF, her: we needed somewhere else cool to go next) it was Time to go, ahead, do it, call him.

It is important to remember that this was the Land Before Time iPhones. (See aforementioned daguerreotype situation.) We had cellular devices, sure, but we barely texted and we certainly didn’t Google anything. So when we wanted to be all like Heyyouout? we more often than not — wait for it — called the other person. With our actual spoken words and inflections and pregnant pauses and nervous laughs and meaningful…sigh(s). There was, I’d argue, so much more spontaneity. So when I, on my piece of shit silver flip phone, at 100 V. Vodka Diet Cokes o’clock, stalked called The Hipster and he yelled through the phone, amidst the din of Saturday night bar crowds, to meet him at “the bar with the green light,” I thought: that is a completely manageable task.

Now, I don’t know if you know this, but there approximately Eleventy Fuckton Million bars in New York City. And This Fuckin Guy gives me the color of a fucking lightbulb as the ONLY distinguishing feature of where I’m supposed to meet my destiny, I mean, him. A true testament to insanity love, neither BF nor I balked. Can you imagine what four-square-yelp-google-map-location-pin-air-drop-box-geotag fuckery would ensue now if someone did this to you? But, nope, we were just like dope, another layer to the Adventure. We had lit-er-ally (and I’m using that correctly for once) no idea where we were going. Well, ok, we knew it was below 14th street, because, duh.

So, off we went. I have no idea what time it was or how many places we stopped in on the way. I do know that I had already broken one martini glass (and would go on to break two, yes two, more that night) because I for sure definitely needed to be drinking martinis all night. Wut. Gross. But lo and behold, an hour or seventeen later, we turned a corner and nuh-uh, no way: a bar with a green light. As we entered the dark Alphabet City dive, I thought, surely, this had to be, please sweet jesus let it be, OMG THERE HE IS this is the place. Twenty-two, drunk and in love, this was not coincidence, or the consequence of only sketching around the same neighborhoods. Nay, NAY, this was MOTHERFUCKING FATE. The gods, all of them, (The Hipster was Indian, so I was kewl with being Hindu now, duh) had blessed this trainwreck union.

Shenanigans! Mayhem! Drinking! Dancing! Ensued! From No Malice Palace (the name of which I didn’t learn for years) we went to Joe’s Pub, which at the time had super exclusive club nights that were impossible to get into. (I have no idea if they still do because I know zero things about being out after midnight anymore.) Naturally, The Hipster got the three of us in. Naturally, I broke another martini glass, tried to take my shoes off, got yelled at by the bouncer because of the aforementioned broken glass, and was just all kinds of ridiculous. At some point in the merry havoc we lost BF to sleep, a slice of pizza, a dude (all three?) and we were deliciously alone.

Because at some point the bars do actually close, soon he was walking me home. It should be mentioned that for that first year after we graduated, home was technically my parents’ house (SO much has changed. Ugh. Anyway.), but I spent my weekends between BF’s law school closet dorm room with her sweet twin bed and The Hipster’s more adult than me apartment in Murray Hill. Anyway, after hours (hours) of traipsing around all the Villages in the land I could no longer deal with the death traps shoes I was wearing. So I took them off as we strolled, slowly, taking each other in, proceeding to cut my foot (that was my cue to put my shoes back on). The Hipster, under the guise of making sure I was ok, told me to stop walking, leaned me up against the building (Remember: NYU. Classy.) and leaned in close.

After a cursory look at my foot, that was probably now a deep shade of gutter punk, he grabbed my face, pulled me in and finally there we were: sucking face at four in the morning across the street from people probably getting shanked in Washington Square Park. Always up for a public show of gallantry, in the middle of our make-out, The Hipster verbally assailed a stranger in scrubs medical student on his way home from being up all night (probably dealing with drunken assholes like us). Not letting me go or breaking our closeness, The Hipster asked him to examine my bleeding foot. I melted into him, not caring at all about the foot or the doctor, only that I could feel the heat rolling off him, feel his hands letting me know that I was his. The man/maybe doctor assured me my foot was fine and maybe, MAYBE, I should put my shoes back on.


1 | The Hipster: The Beginning

In May of 2003 I graduated college and two weeks later found myself in a baptism by fire crash course none of it helped program to become a New York City public school teacher. Teaching had never been what I set out to do, or wanted to do, for that matter, but I needed a job. I had dabbled in journalism, writing for my college paper and the New York Daily News, but my real dream was to be a music journalist. As Rolling Stone wasn’t knocking down my door, there I found myself under fluorescent lights at Brooklyn College with a motley crew of recent college graduates and change-of-career idealists who all had some delusion that we were going to change the world somehow. That basically meant teaching Hip Hop as Poetry. I’m sure your mind is blown.

Right in the center of our spastic little band of dreamers, as we all bonded over code-switching and cheap drinks, was The Hipster: holding court and being gregariously altruistic. The first time he ever spoke directly to me, we were sitting in a classroom, both pinned in by those horrible desk-connected-to-chair contraptions. The Hipster turned to me and asked, in an overly gracious manner, a. If I had any lotion and b. Did white people get ashy? It took maybe 3.25 days for me to be an absolute goner.

That Feeling: the flutter in your gut that feels like potential and unfettered-no-agenda-possibility — of the lusciously tangible Something that could happen between the two of you. It’s getting dressed in the morning with the anticipation of, hopefully, seeing him and wondering if he’ll sit next to you on the train so you can spend the ride sharing stories (yours: halting and self-conscious, his: bewitching and implausible). It’s unexpectedly running into him in the hall and sharing a hurried, whispered moment; the exhilaration of hearing his laugh (deep, throaty and unrestrained) at something you’ve said, ringing in your ears for hours afterward. And all of that building, building, picking up electric momentum into this agonizing blur of OMG maybe tonight could actually be The Night.

Tall, brown and charismatic, he wore skinny jeans before it was a thing for dudes to do. I mean, really, it is very possible they were girl jeans. Who cares. He looked delicious in them. And, once I got over my initial stuttering ima-just-stare-at-you-when-you-talk-to-me Shyness, we got on like a house on fire. We talked music, books, New York City — still the three greatest loves of my life — and we laughed. A lot. It was The Best. That summer was a blur of grad school Jack Daniels and The Hipster. Instead of mastering Delaney cards, we became fluent in the Lower East Side. We stayed out way too late, did far too little homework and flirted our fucking asses off.

It is important to remember, however, that, ALL SUMMER, The Hipster and I, our tragic heroine, were Just Friends. There was the whole nuisance business of the aforementioned roommate, I mean girlfriend, I mean, wait what? He has a girlfriend? I found out this crucial piece of information detail one day after class when a group of us were walking to the subway. Someone was mentioning how flirtatious he had been and wasn’t that weird because he lived with his long-term girlfriend. So many red flags in one sentence. So much choosing not to care. (That definitely wouldn’t come back to bite me in the ass, like not at all. Nah, surely not. Ugh. Anyway.) All I knew was how alive I felt when I was with him. His laugh was the kryptonite to my will-power.

At the end of August, The Hipster, Our Friend, and I went to at job fair at some generic hotel in downtown Brooklyn to try to get jobs. The three of us had become a crew within the crew, raising a lot of hell, shirking a lot of responsibility. (Are you sensing a theme, yet?) However, the summer was hurtling toward a close and we seriously needed some jobs.

Sitting next to him in some dull as rocks orientation about how to like talk to potential employers or something earth-shattering like that, I was aware only of how close his arm was to mine. I think I would have agreed to work in a Last Chance school in the northernmost part of the Bronx if it meant he’d just make out with me right then and there. A few minutes into the spiel he leaned over to me and whisper-asked what I was doing later that evening. (Uh it’s cool, not too much, just pledging my undying love and devotion to you.) I told him that I planned to go to the happy hour one of our colleagues had organized. He pierced my soul looked me right in the eyes and said, “Happy hour is for kids. You’re going out with me tonight.” Fucking swoon. Just let me die happy right now.

Trying to play it super cool and aloof (lololol) I asked him, so, like, what were we going to do. When his response was, “Crashing a Sex Pistols party,” admittedly, my first thought was, “Those guys are definitely dead. Maybe this dude is a little whacked after all.” My second thought was that, really who cared, because he could have said, “Yeah they are but we’re having a séance over Sid Vicious’s grave,” and I would have replied, “Cool cool. Sounds good. Should we say 7? You have a ouija board or you need me to pick one up?” Now, for all my rebel delusions, it should be mentioned, I’ve never really been a rule breaker. I was kind of a shithead in high school because I had the grades to be, like, out of uniform. It’s safe to say crashing a Sex Pistols party gave me the kind of out-of-my-comfort-zone-stomach-pang that was equal parts holy-shit-this-is-awesome and nerd-anxiety.

So that night, after deigning to have one drink in Brooklyn, I found myself abandoning our other friends, at their pedestrian happy hour, yawn, because I had Better Plans with rock and roll, with adventure, with Him. Of course, with him you never truly got the full story (ie: you heard about the roommate/serious girlfriend obfuscation, right? I mentioned that one?). So, ok, we were going to this party, but how exactly were we getting in? Of course, The Hipster was also the guy who Knew a Guy. He went to see about his buddy who was supposed to be working the door, and standing there alone, in front of the Hotel Chelsea, I began to feel a little less invincible and a little more like I was wearing a black tank top and Converse and that we were probably way out our league. Then, as impossibly cool Industry People filed past me, I caught a glimpse of pearls getting out a cab and about died.

The Hipster had neglected to tell me he’d also invited Our Friend. She could start a barroom brawl faster than anyone I knew, but she also dressed like a fucking Stepford Wife. My rapidly eroding confidence that we were going to pull this off was now in the gutter. This was THE SEX PISTOLS. Take your Dave Matthews Band popped collar bullshit right on home. I could have murdered and buried her right there in the piles of trash on 23rd street, bloodstained Banana Republic skirt and all. I was convinced (convinced) that if there was any reason we weren’t going to pull this off, it would not be our highly-flawed-we-actually-had-no-IN plan, no (no) it would be that floral print midi skirt.

But, that’s the thing about The Hipster: he could Make Things Happen. I don’t know who he paid off, or how much he gave them, but about ten minutes later we were at the bar, ordering whiskey and staring at chilling with Johnny Rotten. We spent the next few hours talking to the odd Pistol, sound tech, roadie, whoever, as long we were still on the Right Side of the Velvet Rope. To be in the room was enough. To feel that we had crossed some threshold of Cool was pure magic. Though, as the night wore on and the crowd dwindled, it became clear this was becoming a more intimate gathering. It also became clear we did not belong there. The security started to move in on us, but we weren’t leaving until we’d had our audience with Johnny.

The Hipster, not afraid of spectacle, took care of this. As we were being told to leave, being herded towards the stairs, he raised his glass, bellowing “Johnny!” across the bar. Standing a step above me, I looked up at him and then followed his gaze to the man ensconced in the private VIP area. Johnny Rotten looked over at us, bored.

“Cheers, Johnny!” The Hipster yelled again. The bouncers moved a little closer. Our Friend and I raised our glasses. And there where Sid had maybe killed Nancy, a punk legend deigned to toast us. He raised his glass, nodded, and went back to his conversation. Unplanned, but synchronized, we all threw our glasses down. As the glass shattered we were officially escorted onto the street. There is zero chance John Lydon remembers that encounter. I will remember that night forever.

If there had been any chance that I was going to wise up and let my infatuation for The Hipster fizzle, that night reduced the probability from Slim-to-None to Hahaha-Get-the-Fuck-Out-of-Here. That night, as we parted ways, and he said goodbye to me, he leaned in close to kiss me on the cheek. He grabbed me by the waistband of my jeans, his thumb looped right underneath the button, just barely grazing my navel. Fuckkkkk. I looked at him, inches from my face, and breathed: “You’re going to be trouble.” He just smiled and said, “You have no idea.”

A week later, he and his roommate broke up.

0 | The Intro

About a million years ago, I obsessed over dated this guy who, if emojis had existed then, I would have absolutely texted about exclusively in terms of the smiley face with hearts for eyes. He had Bad Fucking Idea tattooed in neon on his forehead. E.g.: When we first met, the person whom he exclusively referred to as his “roommate” was in fact his LIVE-IN GIRLFRIEND OF 3 YEARS. It’s possible we started hooking up dating about 30 seconds after they called it quits, and maybe she was possibly still moving her stuff out. Solid start to a relationship, real solid. Naturally, I elected to ignore the gigantic red flags and promptly fall in love.

I was 22, invincible, totally blindingly gaga, and, just absolutely possibly, a little stupid.

Anyway, we dated, we broke up, we dated, we broke up, and then proceeded to torture each other for years afterward by “being friends.” Both fancying ourselves writers we stayed friends under the guise of creative support and being, like, evolved humans, or whatever. In reality, I was still madly in love with him and desperately hoping that over Jack Daniels, our experimental short stories, and literary criticism, our romantic comeback would be staged. He would be in awe of what a devastatingly brilliant writer I was, remember how much he missed throwing me into bed, kissing me all over and falling asleep next to me — realize, in short, how much he just absolutely could not live without me.

So, when he started sharing details (that definitely didn’t make me nauseous or anything) of the epic confessional memoir he was writing that recounted all of the great romances of his 27-year old life, I was like totally cool with that because, like, we were totally just friends, and I was like, definitely dating other people and definitely not waiting for him to realize I was the love of his life. Ugh. Anyway. The idea was to use the women he had dated as the organizing structure of the novel. Each woman would be a different chapter, and using this framework, he’d tell all his stories of grand gestures and bellowing Bukowski from the tops of bars and doing blow off of a canvas in Chuck Close’s studio and whatever the fuck hipster bullshit he was always getting after. (Ok, ok, we had fun with a capital F, let’s be honest.)

I tortured myself listening to all this because I loved him so very much, but there was part of me, as a writer and New Yorker that actually did think it could have been something worth reading. We did, after all, raise hell in New York City. We had, after all, toasted with Johnny Rotten at the Hotel Chelsea and played pool with Little Steven at Ace Bar. It was the era of Pianos and The Strokes and smoking in basement bars like Lit. We were in constant pursuit of Cool. This was our very own, bourbon-fueled, converse-wearing, sucking the marrow out of life Hungover Poet’s Society. Heartbreak and destruction were but a natural byproduct of Life, of Experience, of our 20s. And if anyone had the lying embellishment skills to tell a good story, and pull off a novel like that, well, he really did.

Perhaps picking up on the fact that I wanted to vom each time he brought the book up, he was quick to let me know that of course, of course, I was in the book. (WAIT, so, you’re saying there’s a chance?) First I was Chapter 5, then I was Chapter 3. After some shifting around I was reassigned to Chapter 6 and then, finally, I was Chapter I-Didn’t-Give-A-Fuck. After waayyy too many years of Heart-Torture and late-night Heywhatareyouupto’s, I got waayyy too burnt out on his whole Deal. It always stayed civil, but finally (FINALLY) I was Just Over It. Plus he got married, but, whatever.

If we were to use his organizing structure — and we are, thanks, appreciate it, you owe me one anyway Fuckface — then he would be my Chapter 1. Our whirlwind, drunken, roller-derby of a love-affair kicked off my dating life in New York City — that still isn’t fucking OVER. God kill me. — and what ensued in the following years, I think was always a little bit informed by him. I want, stability, sure, but I want Magic and bravery and rock and roll and someone who will jump with me. When I was 33 I met the man that I was sure was my Last Chapter. We had really and truly started to dig in and build a life together, and, then, one day, it was inexplicably Over. So, I am 37 years old, rapidly careening towards Totally Over It years old, and find myself, once again, single.

I have been dating in this city for the past eighty-five 16 years, and, I am firmly convinced that when Dante Alighieri, the lauded Italian poet of the Middle Ages, wrote his Inferno, describing in horrifying detail each of the nine circles of Hell and the assortment villains, reprobates and ne’er-do-wells being tortured for eternity, he was writing about not the mythical underworld of Tartarus, but rather of dating in New York City as a 30-something. I’ve met men in bars. I’ve met men at work. Most of men the men I’ve been romantically involved with, however, I’ve met through the fuckery known as online “dating”. I find myself somewhere I didn’t think I’d ever be in my mid-30s — Omg, wait, is 37 LATE 30s? Ugh. Anyway. I find myself somewhere I didn’t think I’d ever be: crafting witty (wittyish?) opening lines and awkwardly shotgunning drinking a glass of Sav Blanc whilst trying to determine if the Cylon man sitting across from me is even tolerable let alone desirable.

I have no answers, but I do have some stories. Some are good stories, some are bad stories. I am not bitter (fucking miraculously), but I am, obvs, SALTY AF. What follows is a ridiculous deep dive into my dating past. I can promise honesty, compassion where it is warranted, but to all the men I’ve dated: you have been weighed, you have been measured, and you have been found wanting.

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