So after our near psychotic break and almost getting married in Tijuana seeing the sights in San Diego, it was time for us to head north. The Hipster had a friend living in Venice Beach and said friend kindly agreed to let us crash for a couple nights. We decided to drive up the meandering, inefficient, coast because hello convertible + road trip = swoon, Romance.

Somewhere along the way we stopped to get gas and The Hipster spotted a Tower Records or Virgin Records or some other relic brick-and-mortar entity that sold culture in tangible formats. Two CDs (CDs!) had just come out that he needed to get us. His eyes twinkled as he unwrapped the cellophane and Michael Jackson and The Streets quickly became the soundtrack for our trip. With the top down we glimpsed the glittering Pacific and talked about our jobs and our students and how much we wanted to help them, but also how happy we were to be the hell away from them. (Because, ugh, KIDS, amirite.)

We met The Hipster’s friend at Mao’s Kitchen and they caught up on each other’s lives. Watching The Hipster tell a story was its own spectator sport, so I listened happily, basking in that mischievous smile and husky unrestrained laugh. After dinner and a couple beers, The Hipster and I were ready to Go Out. (Haha duh.) The Hipster’s friend wasn’t going to join us. He needed to wait at home for his girlfriend who was returning from a trip. So, two New Yorkers who knew virtually zero things about the City of Angels took very many expensive cab rides to bars far away from Venice, to explore Los Angeles.

On the Sunset Strip we drank bourbon at the Whisky a Go Go and talked about music, about The Doors, because how could we not. At Rainbow Bar we tried to figure out if anyone in the sea of Mötley Crüe leather pants wearing types was in fact anyone from Mötley Crüe. At The Viper Room, in direct contrast with the jaded Hollywood elite drug-overdose vibe of the club’s legacy, we listened to a band, clad in Hawaiian shirts, whose name we didn’t know, but we instantly dubbed The Polynesian Happy Band. Maybe bolstered by the infectious, cloyingly upbeat tropical music, The Hipster leaned in and told me how happy he was that we had taken this trip together. Same, same.

It is perhaps (PERHAPS) possible we staggered back to his friend’s apartment in Venice a little too late and a little too loud. I have a vague sense that there was a skosh of tension, and that maybe The Hipster’s friend’s girlfriend wasn’t so stoked we were there? Honestly I don’t truly remember why, but we ended up getting a hotel room for our second night in LA. During non drinking hours daylight, we drove Mulholland Drive and ate tamales at a farmers’ market in Santa Monica. That night we found a Travelodge or something that seemed innocuous enough. Upon attempting to check-in, we were checked-out by the Indian hotel manager who (rude) asked if we were married. First of all: Noneya. Second of all: Like, omg Mister, lemme tell you about the other night.

A bit subdued and out-partied, we ditched our stuff in the room and headed to The Dresden. A mainstay in Los Feliz, the decor in The Dresden hasn’t changed since the Rat Pack was sipping old fashioneds at the dark wood bar. Marty and Elayne, the long-standing lounge act, were off that night so we sat in the dining room and nestled into the white banquets to eat a civilized meal. I probably ordered a dirty martini (whyyy), but The Hipster ordered a drink called the Blood and Sand. It had Scotch in it (blech) and it sounded manly and gritty, he said. It was hot pink. The waiter had barely put it down on the table before The Hipster was asking me to trade drinks. I categorically refused, he survived, and after our steaks we went back to our den of premarital sin hotel room for an early night in.

Curled up in bed — both secretly happy to be in, alone and without agenda — we flipped channels on the TV. When A Bronx Tale came into view, I put my hand over his, stopping the flick flick flick of the remote. Watching Chazz Palminteri drive in reverse down one way streets and rough up motorcycle gangs, I felt homesick for New York. We hadn’t been away that long, and Calogero’s New York was certainly not my New York, but New Yorkers have a funny relationship with LA. In the dusty, smoggy sprawl of lights and on-ramps and cars, ranches and stucco, we often feel at sea. Its vastness is alarming. I want to go home, I said. Not yet, he whispered, pulling me in closer, our California adventure isn’t over quite yet. And it wasn’t.

In the interest of efficiency, we drove through cow country (sweet jesus that smell) and made our way to San Francisco. Our first stop was the Mission where we met some of my friends at Casanova. As we played pool, they got to know The Hipster and I reveled in my worlds colliding. The Hipster had his crew back in New York, but here we were in the middle of mine. These were/are/will be always and forever My People; the stand in traffic jump on a plane at a moment’s notice no judgement ever kind of friends that make it possible to survive the muck and bullshit of this whole bizzare Adulting freak show LIFE Situation we got happening here. I wish for everyone that they experience this level of friendship at some point in their adult lives. It is like having access to extra oxygen. And, duh, My Friends are devastatingly smart, searingly funny, strong AF and just like the Most Fun Ever. You’d for sure want to hang out with us. And, yes, I was in a sorority, thank you for asking.

Talkative Friend and Very Tan Friend moved to The City after we all graduated from Berkeley and were our base of operations for the SF leg of the trip. So after Casanova, The Hipster and I parked Jezebel in a garage and installed ourselves in TF and VTF’s living room. Prone to being um, completely rambunctious a bit playful, when I’ve been drinking, I remember seeing him walk toward me down the long hallway and tackling him. Me straddling him on the floor of the hallway, clad in our standard-issue Lower East Side uniforms of ripped denim and faded black, both hysterical laughing, Talkative Friend took one look at us and declared us the most New York looking couple she’d ever seen. A higher compliment could not have been given. Into the unfailing airy mellowness that is Northern California we had brought the raspy whiff of bourbon, smoke and havoc.

On a whim, The Hipster had decided that he wanted a mohawk. So, at the Walgreen’s on the corner we bought clippers — and also saw Scott Speedman buying deodorant (omggg hi Ben Covington, hi). We set The Hipster up in the kitchen, and he handed me the clippers, but as soon as I got close to his scalp, I balked, fearing I was way too tipsy I’d disfigure that beautiful head of his. So, Take Charge Friend, nonchalantly whisked the clippers out of my hands and gave The Hipster his faux-hawk. TCF is quite possibly the least mohawkiest person I know, for sure the West Village to our East Village, so that she effortlessly ratcheted up The Hipster’s punk rock quotient in the middle of what may as well have been a sorority house, was just absolutely perfect. Him, newly shorn and me, in my second home, we spent the next couple of days doing what any self-proclaimed beatniks would do: strolling through Haight-Ashbury, wandering around Berkeley and hoping for a Ferlinghetti sighting at City Lights.

For New Year’s Eve we had all bought tickets to a club (ahahaha A CLUB!) called DNA Lounge. TF and VTF had psychotically graciously offered to host the whole messy lot of us for getting ready/drinks before and a find a spot wherever there is space sleepover after. So, basically, college again. Everyone was assigned a key buddy, the person they had to stick with for the evening no matter what because let’s be honest, who knew where everyone would have scattered to by 12:01. I had the disastrous brilliant idea to provide tequila for the pre-party. My only taker was Legs For Days Friend who humored my claim that shots would be omg so fun. (Narrator: They were not so fun.)

Upon arriving at The Club, Legs For Days Friend promptly vomited. Like a lot. It was awful. We had to tell the staff that someone (SOMEONE) had been ill in the ladies room. (Okkk soo mayyybe the tequila hadn’t been the best of ideas.) Your typical New Year’s Eve bacchanal ensued. We lost people, gained people, drank things, danced things. The Hipster’s suit jacket came off, collared shirt unbuttoned to expose the CBGB shirt underneath. A sweaty mess, my makeup melted off. Then, as midnight struck it was as if the generic gray club had faded away and the veil to an enchanted wonderland had been lifted. Club kids en masse appeared as if from nowhere. All of a sudden Marie Antoinette was on a platform above me and a butterfly was gyrating next to me. Spinning drunk, I was instantly overwhelmed. The Hipster, transported right back to his chaotic steeped in lurid excess didn’t want to ever relive them Limelight days, told me it was time to leave. Few things ever unnerved The Hipster, so when I saw the look on his face, I knew that it was, in fact, time to go.

Exiting the club into a new day and a new year, we discovered that it was absolutely heaving can’t see across the street raining. We also discovered we had no idea where we were. (Perhaps we should have been key buddies with people who were actually familiar with San Francisco? Maybe? Ugh, anyway.) Back in the olden days with no smartphone and no Uber, what were two drunk New Yorkers to do? Get on the first bus driving by? Sure, that sounds like a good idea. After the bus driver kindly informed us we were traveling in precisely the wrong direction, we disembarked and somehow found a guy in a car looking to make some money who thankfully didn’t kill us black gypsy cab that probably cost The Hipster a grand to take us like a mile. Miraculously, we all found our way back to the apartment in varying states of dress and undress and distress.

On New Year’s Day we had a disheveled brunch with my friends and then it was time for us head to the airport. Our California adventure was, in fact, over.

But, wait! Not before we got into at least one stupid couple on a vacation fight!

Hungover and gloomy about vacation being over, we shuffled to the parking garage to pick up Jezebel. When the attendant asked for the ticket, The Hipster looked at me expectantly. Yes? Can I help you? asked my answering look. The ticket? he asked. I, VERY confidently, told him I had no such ticket and since he had been driving he def had it. He, VERY confidently told me that he remembered handing it to me. The parking attendant watched as we both swore on all things holy that neither of us believed in that the other ABSOLUTELY had the ticket and hurry up find it because we are going to miss our plane. He watched as we verbally eviscerated each other tore our suitcases apart. He watched as we turned to him in defeat, pleading in our eyes, and told him that the ticket was gone and could he pleaaasssseeee do us a solid and let us have the car. After The Hipster paid him off raking us over the coals a bit, the attendant relented.

By the time we got through security we were speaking again, bemoaning the tragedy of impending work and winter. Never wanting to face reality, we landed and promptly took a cab to Schiller’s, suitcases in tow. (Never say die! Keep the party going!) Over New York Sours and cuban sandwiches we rehashed our favorite nuggets from the trip. The adventure was over, but it felt good to be home, back on the Lower East Side up to our same old bullshit and wondering what the winter had in store for us.

A week later I found the parking garage ticket in the back pocket of the jeans I had allegedly been wearing when we parked the car.

Before our late winter excursions with rockstars and to emergency rooms, The Hipster and I spent the week after Christmas in California. After our Thanksgiving break-up, I immediately made plans to visit my college friends during winter break. When The Hipster and I got back together after one drunken night of mayhem discussing our like, feelings and needs and stuff (those are the things, right?) it was decided that he would come with me. So what had previously been an eat drink eat pray love I am v sad single person best friends please console me trip, became an omg we are real couple road tripping like v beatnik free spirits I am happiest girl ever trip.

We flew into San Diego and planned to make our way up the coast over the course of the week. The only commitment we had was New Year’s Eve in San Francisco. I was too young (lolol too young!) to rent a car, but The Hipster was old enough my knight in shining armor so he rented us a convertible, which we promptly named Jezebel. There is nothing like the euphoria of taking off in gray bleak December New York and five hours later standing in sunny palm-treed San Diego. We were absolutely giddy.

After doing some wholesome things like walking on the beach and taking a tour around the high school I graduated from, we headed south. Because, really, what else is there to do in San Diego except go to Tijuana and ruin one’s life see the culture? I mean San Diego is beaut, but TJ was exactly the kind of Kerouac-ian debauchery adventure that appealed to us. We stayed at some human trafficking rendezvous point motel close to the border. Once I discovered the burn marks on the worn-out green carpeting (me, hopeful and naive: iron? him, somber and definitive: crack pipe.), I made him stand at the door to watch me retrieve whatever I had forgotten in the car. It would have been très unromantique to have gotten kidnapped in the parking lot.

Sixteen years ago it was relatively easy to cross the border. I’m assuming it’s nightmare now. Because, really, what about our government isn’t an unmitigated disaster? Ugh, anyway.

Our first stop in Mexico was the bar adjacent to the bus station. Because why wouldn’t that be a good idea? Right. As we crossed the threshold into the narrow, dark, very much locals only dive, it was exactly the record scratching to a halt moment you’d imagine. I was absolutely the only woman in there, and I’m pretty sure I was only allowed in because I was with a man. Always arrogant enough to at least act like there wasn’t a room in the world in which we didn’t deserve to be, we ordered our tequilas and drank them politely while also silently communicating that we 100% needed to leave. Perhaps not as actually back-alley gully as we’d have liked to believe we were, The Hipster and I moved out of the dark shadows of those quiet streets onto the fluorescent shitshow of Avenida Revolución.

There were many stops on our journey that night. I remember snapshots: sitting ensconced in 1970s velour booths and discussing Salinger while listening to a jazzy lounge act, eating chips and salsa in a place that was dead but beautifully tiled, dancing for five seconds in some horrifying display of American teenage drunkenness club on Revolucion before escaping to the curb where people were trying to sell us drugs, but I only had eyes for the man making and selling tacos out of a shopping cart. The Hipster wouldn’t dare touch the the street meat, but while I navigated taco procurement, I remember him looking at me with That Look. The one that says Everything: that this moment is perfect and unexpected and ridiculous and doesn’t make sense and is an isolated bubble of happiness and love and longing and we are meant to be together and have adventures like this and

Halfway through my mad cow taco, The Hipster asked me to marry him.

Reader, I married him.

Lololol jk jk CAN YOU IMAGINE? I mean, had there been a church or justice of the peace open, or if the taco guy had produced, from the depths of his shopping cart, a cocktail napkin with the word “ministro” scrawled on it, come on I would have def married The Hipster, obvs. Clearly we were 347 sheets to the wind tipsy and this was a moment of the whimsical Kerouac-ian grand gesture disregard for convention we were predisposed to, but in that moment I was blindingly in love and looking at a man who was looking at me like I was the only person in the world. Lucky for us, and our parents, and their respective lawyers, it was the middle of the night and the only thing to do was head back across the border.

That winter, other Big Things happened too: The Hipster got a faux-hawk and I got bangs. (Uhm, yah, hello, told you we were Cool.) As if I didn’t already want to jump him the second I saw him, man, that faux-hawk put me over the edge. So effin hot. On Valentine’s Day he woke up earlier than I did and went out to get us coffee. We, of course, obviously, duh, had no actual plans for Valentine’s Day because ugh lame how relationshipy conventional, but he returned to the apartment with an iced coffee in one hand, faux-hawk perfectly tousled, sunglasses on and a rose between his teeth. He handed me the rose, pulled me in close and whispered, “Happy Valentine’s Day, baby.” It is, without a doubt, my favorite mental image of him.

Blissful as these moments were, the real world was (gawd, rude) lurking outside that highrise door. In the midst of dining on Moroccan food amongst the rose petals at Chez Es Saada, and colonizing Williamsburg (Black Betty!), we did actually (sigh) go to our places of employment. I spent many a very early morning on the Q train (back when the 2nd Avenue subway was still a laughable urban legend), headed into deep Brooklyn, clutching a coffee and everything bagel in a vice-grip, whole body locked up in a bourbon induced rigor mortis, simply trying to fend off my most certain and imminent death by Jack Daniels. Because, obviously, who doesn’t go to APT until 3 in the fucking morning on a Wednesday when you have to be at work — IN SHEEPSHEAD BAY — by 7:45 in the fucking morning? Like I can’t. I exasperate myself. But, yes, I was a v responsible and well-prepared 6th grade English teacher, thank you for asking.

After we finished our summer “training” — there’s only so many times you can be told “Don’t smile until Christmas” before you tune out entirely — program, we all got down to the actual work of teaching in the city’s public schools. This is not a task for the faint of heart, just FYI. No, but like for real I can too easily identify the scent of radiator-charred mouse. Gross. Sure, sure, teaching includes many vacations and that is super kewl. Teaching also includes trying to: get kids to care, teach kids to read, socialize children who have absent parents, care for children who have abusive parents, protect children who have helicopter parents, make ends meet by getting a second job, teach kids to write, redirect adolescent anger, defend oneself from aforementioned anger, beg for supplies, buy supplies when there are none, survive petty administrators, survive ignorant fellow “professionals,” prepare students for standardized tests, attempt to instill creativity and critical thinking as innate modes of being, possibly carve out time for lunch because cool cool this was all before noon and oh, I also mentioned the rat luau right? So, right, the New York City Department of Education is a dumpster fire.

You are shocked to hear that it was a love-hate relationship from the outset, for all of us. The Hipster and Our Friend had, at the eleventh hour, secured jobs at a Last Chance school, teaching almost-adults. This basically meant trying to get emotionally disturbed teenagers to read The BFG, care about themselves, pass a class and not go back to/go to jail. They were in The Trenches. Like straight up Battle of the Somme Trenches. I was less so. By some act of divine intervention, I had gotten hired at a gifted and talented school (I mean one of the “talents” could be gym, but still) mere minutes before I was about to sign my contract at a vo-tech high school where, when I arrived for my interview, the NYPD officer assigned to the school had taken one look at me, shook his head, frowned, and said “No.”

While The Hipster and OF were just trying to stave off complete anarchy, I was trying to survive a principal who maintained her reign of terror order by utilizing a combination of subtle psychological warfare and very public vitriol. She was about five foot nothing and maybe the scariest person I’ve ever met. On any given day my feelings toward teaching bipolared between “Omggg I have most important job everrr John Dewey wuld be soooo proud of my Wrinkle in Time unit that nurtures multiple intelligences” to the emotional embodiment of Marshawn Lynch’s sunglasses-on-just-here-so-I-don’t-get-fined press conference. There was no in between. I’m still not entirely sure a 22 year old has any business being in charge of anything, let alone the emotional, developmental and physical well-being of 11 year olds, but like, in the end, no one died so, it’s fine.

The best thing about being is a teacher is, um, sure, the feeling you get when you, like, reach a kid, or inspire them or whatever, but also have you heard of Snow Days. As soon as the forecast predicts enough snow to maybe, potentially cancel school, the excitement in the building becomes electric, palpable and full of promise. The city is notoriously obstinate about closing school tho (dicks), so we rarely dared get our hopes up.

On the evening our story takes place, however, I left my boxing gym to find that my phone had exploded while I was getting my ass handed to me by the heavy bag. Ok I had like three voicemails. (Lololol voicemail.) On the move and jumping on the train, I heard only snatches of the messages and things like “school” “snow” “cancelled.” Omgggg COULD IT BE?? Quick someone turn on the news and see if it’s true! (The news! On TV! I know I’m three hundred years old. Get over it.) I rolled into Best Friend’s dorm like a maniac spluttering incoherent blurbs of joy and did she want to go out because of course (of course!) we were going out.

About thirty seconds later I found myself at Max Fish with The Hipster, OF and The Hipster’s crew (like I said, super tight, always game). The giddiness amongst us was tangible. We lived for this sucking the bourbon marrow out of life kind of spontaneity. The Hipster, always with the flourish, able to apply the veneer of romance to every moment, beckoned OF and I to the bar. He ordered us Jack and Gingers, no ice, and cocked his head toward the door. It was tradition, he said. Heading outside, onto Ludlow Street, we three unlikely friends filled our drinks with the highly toxic and assuredly diseased freshly fallen snow, and toasted to each other and this complicated career we had undertaken.

And then we drank. A lot. (You are sensing a theme or nah?)

Eventually it was decided that we should leave Max Fish and maraud our motley crew somewhere else. The snow was falling fast and heavy by that point, blanketing the Lower East Side. It was a Tuesday or a Wednesday and the streets were quiet. Except for us. Like banshees we ran down Ludlow, on the sidewalks, in the streets, bellowing and screeching, radiating pure joy and drunkenness. As we turned onto Rivington, all skidding and flailing in the snow, The Hipster took a header. Careening down the street, he had caught some ice and went sliding, belly to the ground, hands outstretched and ohhhh that’s a lot of blood.

We should have gone to the hospital. (Narrator: They did not.) At The Hipster’s insistence it was a mere scratch (Narrator: It was not.) There were to be more drinks! more carousing! the night was still young! Clearly, the logical choice of destination, if not the sanitized halls of a hospital, was Welcome to the Johnson’s. There really was a lot of blood, though so, like, maybe we should um, get a bandaid or something? Dutiful girlfriend that I was, I went promptly to the barkeep to request their finest first aid kit — aannnnd two Jack rocks splash of Coke kewl thx. (I mean, he was wounded, he needed anesthesia, duh.) Now if this doesn’t tell you anything about the Lower East Side before it became entirely sanitized by dbag Patrick Bateman wannabes, I don’t know what does: a mob of already shmagasted people bulldoze their way into the bar, one of their party is bleeding profusely, a girl slurs asks for a first aid kit while ordering drinks, and not one person in the place flinched.

Now it should be mentioned that, at this point in our relationship, there was always a bit of underlying tension between OF and I, and it had everything to do with The Hipster. OF is simply a naturally competitive person and I was always a bit insecure of my place in the dynamic. She and The Hipster had become very close, very fast. They spent far more time together since they worked in the same school and there was part of me that was always a bit jealous that they had the same war stories, grievances and successes. If we weren’t in grad school classes, they were always often at happy hour together, after work. I worked in the ass-end of Brooklyn and lived on Staten Island. I wasn’t making it to mid-week drinks in the East Village on the reg. As the romantic interest, and not the buddy, I felt my role in his life was always a bit more tenuous than hers.

So, when OF attempted to take control of the triage station we had set up on top of the Pac-Man console, I bristled and pulled the girlfriend card. I knew what I was doing (haha yeah sure ok). We would just wrap it up because it wasn’t like a piece of twisted metal protruding from a manhole cover had ripped The Hipster’s hand open at precisely the juncture where his thumb met his palm, or anything. (Narrator: That is precisely what happened.) I was going to be the one to help him and no thank you leave me alone, I will not listen to your attempts to yell at me counsel me that using gauze to stanch the blood flow and bandage his hand was the worst idea ever ill-advised.

The next morning I awoke to screams coming from the bathroom. Like, really, no scenario in which that’s a good thing. I hungoveredly limped ran as fast as I could to the bathroom, where I found a murder scene The Hipster standing at the sink, horrified: blood covered every surface, including himself. He had attempted to remove the gauze that I had so tipsily lovingly applied. I felt queasy looking at him. Was it the blood? The leftover bourbon that roiled around in my stomach? The guilt of knowing that OF had 100% completely been right and that the gauze was 100% a terrible and wrong decision? An agonizing trifecta of the three? In trying to close itself, The Hipster’s wound had started to heal around the gauze. When, in the morning, he wanted to look at said wound and see what damage had been done, The Hipster had unceremoniously ripped off said gauze, thereby eliciting aforementioned horror film screams and SVU crime scene.

We took a cab to the ER, blood soaking through the white t-shirt that wrapped his hand. To his credit, The Hipster did not blame me for the new level of heinousness this injury had taken on — at least not outwardly — even though I was assuredly at fault. Getting out of the stuffy, cologne soaked death trap vehicle, a tsunami of nausea washed over me and I faltered, holding up our mad dash into the hospital. The Hipster looked at me expectantly like hello ER, blood, Situation Happening over here. I waved him in and told him I needed a second. He could fill out the admittance forms with one hand, right? (Ugh, gawd, men, so needy, amirite)  He left me for a lost cause and hurried through the sliding doors. I promptly vomited in the curb slush. I remember thinking it’s kewl you are not complete hungover degenerate bc you outside the ER, people will just think aw man too bad for her she is v sick person. Ugh, anyway.

Sitting in an ER to begin with is awful. Sitting in an ER deathly hungover is just a really deep layer of hell I hope you never experience. After what seemed like a lifetime, I was called in to see The Hipster. The doctor was keen to tell us that of course (OF COURSE) we should have brought him in last night. He absolutely had needed stitches and because of the whole, um, gauze debacle, there would probably be some scarring now. The Hipster simply shrugged. He was not unfamiliar with scars. He had many and he wore them proudly. The stories associated with some of them were harrowing, at best. This scar would just be one more to add to canon; one that told the story of some stressed out teachers, a bit of snow, a lot of bourbon, and a nearly severed thumb.

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.

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 11^th 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, 2^nd 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 11^th 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.

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.

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 23^rd 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.

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.