This Might Be Too Personal: And Other Intimate Stories

By Alyssa Shelasky

A frisky, feminine, funny, and profoundly genuine essay collection on relationships, sex, motherhood, and finding yourself, by the editor of New York Magazine's Sex Diaries.

Alyssa Shelasky has a lot to tell you.

In this hilarious and intimate essay collection, Alyssa navigates life as a wild-hearted woman and her thrilling career as a sex, relationship, and celebrity writer in New York City. From double-booking an interview with Sarah Jessica Parker and an abortion appointment and unsuccessfully quitting sex and men entirely to have a baby via an anonymous sperm donor, to hooking up with a hot musician while eight months pregnant and then finding her life partner but vowing to never get married, Alyssa's essays paint a deeply genuine, romantic, and uproarious portrait of a woman who craves both love and lust, and refuses to settle or sacrifice her fierce inner-spirit, sometimes to her own regret and detriment. And she's not afraid to give you every single beautiful, messy, embarrassing, and emotional detail of her bleeding heart and busy bedroom.

This Might Be Too Personal is like having (several) drinks with your best friend who has seen, heard, and done everything. Literally, everything. Told in a refreshing candor with jolts of humor, undeniable relatability, and irresistible energy, Alyssa’s book is the ultimate meditation on living an authentic life with big feelings, hard decisions, and the small victories and painful mistakes of motherhood, womanhood, and profound independence.

• Language: English
• Publisher: Macmillan Publishers
• Release date: May 17, 2022
• ISBN: 9781250810892

Alyssa Shelasky

ALYSSA SHELASKY is the editor of New York Magazine's Sex Diaries and the author of Apron Anxiety. She is also starring in and producing the Sex Diaries docuseries on HBO. She has written for numerous publications including the New York Times, People, Town & Country, Women’s Health, Refinery29, Cosmopolitan, and Glamour magazine. She lives with her family in Brooklyn Heights.

Book preview

one

Are You Okay?

I wasn’t sure if I’d make it across the West Side Highway alive.

Everything about my body and mind was unsteady as I stumbled ahead—and the traffic was coming. I had no shoes on. My eyes were blinded by octagons of tears and particles of cobalt-blue mascara. It was somehow too much to carry my crocodile clutch (fuck clutches), my strappy heels, and the heavy, clunky wedding present in the glittery gift bag, especially because my hands would not stop shaking. So I consolidated the bags, chucked the shoes in the street, and dragged myself to the other side.

That’s when my left ankle gave out. It does that sometimes. There is nothing more undignified than gracelessness. I fell to my knees on the sidewalk. My long, silky blush slip dress ripped, revealing my scraped and bleeding legs. But I got right back up and kept on going.

If I turned back—which I would not—I could still see Chelsea Piers, and the big fancy wedding I was running away from. It was not my wedding that I was running away from. I had called off my wedding—which would have been much more indie bride style—the night before. This wedding was for my now-ex-fiancé’s friends, where my now-ex-fiancé was the best man. He was, indeed, the best man: the best man I would ever be in a relationship with, even though I still couldn’t marry him.

I had broken his heart the night before while sitting on our beige Pottery Barn couch in our beige one-bedroom rental, in a beige high-rise building in the Flatiron District. After five happy-ish years together and one large diamond ring (which I picked out myself and definitely did not hate), I told him it was over for no reason other than not loving him enough. That’s all I had, really. I didn’t love him enough or desire him enough or need him enough or want him enough to lock into a lifestyle together forever. I only said the love part, though—why make things more complicated than they had to be?

Whatever words I used or didn’t, the breakup was brutal. He was young and sweet-natured and untarnished, and had yet to develop the coping skills for life’s cruelties and disappointments. (Neither had I, really, but I was built tough yet tender. It was my brand from birth.) We both cried all night and I was surprised by how hard it was on my heart, given this was what I wanted. I did love him, and I was going to miss him: his sparkling green eyes, the way he would get ridiculously excited to introduce me to a new restaurant that he hoped I’d think was cool, how he playfully called me My Loony Lys whenever I’d start to unravel without explanation. My Loony Lys would always make me laugh and temporarily defuse things.

It was savage to hurt the nicest person in my life like this. But it was worse prolonging the pain. I wasn’t coming home at night. Some of his friends had seen me out at clubs and off the rails. My life was full of moral ambiguity, but I couldn’t bear to make a fool out of him.

My new job as a reporter at Us Weekly and my new crowd that liked to party kept me fluttering around the city till the sun came up. The nightlife was all heat and sting and it felt like exactly the place I wanted to be, doing exactly the things I wanted to be doing. It was like: double dates and sake bombs with Cornell frat boys turned starter bankers, or drinking and smoking all night long with celebrities, supermodels, and rock stars? You tell me.

Every other night, I was either messing around with Thomas, a womanizing photographer with whiskey dick, or Trevor, a feral musician with a trust fund. There was Jax, just out of jail, who took me on an erotic date to a car wash in Queens. And Paul, from upstate, who liked to go downstate. I was twenty-five years old and it was safe and consensual sexual experimentation—which I found profoundly pleasurable. But I was engaged. And the fact that I wanted to be with everyone but my very square fiancé was an issue. Honest conversations about ethical nonmonogamy and open relationships were not yet a thing for most mainstream couples, and if they had been, maybe we could have found an arrangement that was right for both of us. Though, he was a traditional guy and I semiconsciously did not want to be a wife, and those parameters were pretty well fixed and very much competing.

The morning after I ended things, with our faces chafed from tears and our eyes stinging from sleep deprivation, my ethics suddenly kicked in and I didn’t think it was appropriate to be a last-minute no-show at this stupid wedding. We had to go together. By the time we arrived, everyone knew we were over. He had told his friends everything the night before so that no one would wonder why we were being weird.

At the pre-ceremony cocktail hour (a phrase I hope to never use again), everyone was gossiping about the breakup, which didn’t really bother me, but it was unpleasant for him. The murmurs and whispers were practically echoing off the harpsichord. When I went to the bathroom, I overheard two girls, who I’m sure were elliptical thin with epic memories from Montauk, talking about me. From the stall, I could only see their perfect pedis in ballet slipper pink. One of the girls was detailing how I once discussed pornography with her boyfriend, which she found to be grossly inappropriate, and the other one added that I was kind of a whore. It was painful to hear, but I told myself I deserved the social punishment.

Everyone made it abundantly clear that I was the persona non grata, and though it was an intense hour of my life that left some nasty scar tissue, I ultimately respected their loyalty to my ex. These were the people who would get him back on his feet with fantasy baseball leagues and Rosé All Day and hookups with cute interns from Merrill and assistant buyers at Bloomingdale’s, and he needed them. I never belonged there anyway.

I assumed, however, that I could get through this timelessly elegant wedding with poise. It was miserable and alienating, but … that’s what passed champagne and deviled eggs were for, right? When I sat for the ceremony, the only people who wanted to sit next to me were relatives with names like Rhonda and Mordi—and even they weren’t so sure about me, energetically. Kind of a whore clanged in my head, but I tried to shake it off and hold my shoulders back like a lady. But when I saw my ex walk down the aisle so defeated and embarrassed and exhausted, in the classic tuxedo we had purchased for him, hand in hand, with his first-year bonus check from the investment bank, it was impossible to hold back the tears.

The dam burst open. My whimpers turned into weeping and the weeping turned into sobbing, and suddenly I was fighting for air. I felt so overwhelmed by emotions that I was choking on them. My wailing was loud and appalling and I could not stop. As if I hadn’t already caused enough unnecessary noise, my unrelenting shrieks were now ruining the whole ceremony. The more I tried to control them, the more the sobbing and choking were amplified. I was crying myself to death and causing a very unfortunate scene. There was no other option but to remove myself entirely. So, mid-vows, I stood up rudely and inharmoniously, ran toward the emergency exit, and busted out of there. Like a nut. Like a drama queen. Like the dangerous person they’d all warned him I was.

Out on the street, gasping for air, I was stunned by what had just happened. Stunned! But I was free. I had hardly floated away like a pretty little petal, but I was free. And that was goodbye. Loony Lys was out.

Why I took this couple’s shimmering wedding gift with me, though, I have no clue. I’d rather have a pap smear than a wedding present. In fact, it was somewhere near the All-Clad aisle one week earlier where I’d made the final decision to call everything off. My mom had taken me to Macy’s Cellar to register for cookware and dishware and where the hell was I? This could not be my life. My mom saw that I was having trouble functioning in the Cellar, sweating profusely, and not enjoying the experience at all. It was an anxiety attack. She reminded me that I could tell her anything, and forced me to let it out, already! So, finally, in front of the stainless-steel pressure cookers, I released all the truth bombs. Everything about getting married felt wrong. I didn’t give a shit about having a wedding or becoming a wife. I was already counting the affairs I would need to have to make me feel alive in the marriage—and I had recently started several of them.

My mom didn’t seem too surprised by any of it, and she certainly didn’t try to turn the bus back around. Hers was the only opinion I ever cared about—then and now. We were always the same kind of complex and unruly woman. She chose a traditional lifestyle with my dad that went against her wild-hearted nature because she’d had a hard childhood and valued stability above any of the whimsical stuff. I had an easy and safe childhood, so I craved trouble, and knew I could get away with it because I had unconditional love and a support system. As such, nothing was more romantic to me than a bad decision.

Without judgment, but also without any room for interpretation, my mother told me that I had to end my duplicitous life and my engagement—and fast. It was monstrous to do this to him, and that’s not who I was or how she’d raised me. Plus, she’s a Virgo, and had months of compulsive planning to undo.

In the countless breakups I would endure following this chapter of my life, this was the only ending where I truly wounded an innocent man. The rest of the breakups would be even uglier and worse—oh yeah, pull up a seat and a deviled egg—but the guys almost always deserved what they got, as did I. This person did not. And that guilt lived inside me for years to come. A lot would go wrong for me, and I would often wonder if it was karma for the way I’d treated him and the damage that I did—not just to this good person but to my own future trajectory.

So, no, I did not cross the West Side Highway into a world of rainbows and unicorns on that tough, transformative day. Not even close. Although something miraculous did happen.

I had just enough wherewithal to comprehend that I couldn’t take the subway without any shoes on, but I also needed cash for a taxi if I wanted to shelter somewhere. Since I no longer had a homeland of my own, the only place I could go was my parents’ apartment in Brooklyn, several miles away. They had recently followed me to New York from Western Massachusetts, where I grew up and where all our family and roots were. And they were just settling into a parlor-floor apartment in Brooklyn Heights, practically days before the real estate market boomed there.

Searching for an ATM, I caught a reflection of myself in a storefront window. What a wreck. Cherry-red lipstick stained my teeth. Turquoise eyeliner and orange bronzer streaked from my cheekbones to my clavicle; my hair was greasy and tangled from the sleepless night before; blood was splattered all over my limping legs. All of the above was saturated in spit, sweat, toxicity, and uncentered energy. I would have given my left tit—already hanging out—for a tissue. Yet all I could do was put one wobbly bare foot in front of the other and walk on. A Citibank had to be somewhere near Twenty-First Street.

That’s the block where I accidentally bumped into somebody. Aggressively. We literally crashed into each other. Like, Boom.

Are you okay? he asked with a kind voice, absorbing the whole situation in front of him.

I barely looked up.

You okay there? he repeated, even kinder, now slightly concerned.

I was in such a daze—a trance, really. So without any acknowledgment of this guy, I said nothing and brushed right past him. Screw it. I’m a New York woman having the worst day ever with a big bag of glittery grotesquerie and I … just … cannot … right now. He’ll get over it. And he did. He kept walking in his direction and I kept dragging in mine.

And then I realized.

That was Ethan Hawke. That was Ethan fucking Hawke!

Everyone knew Ethan Hawke was my number one celebrity crush. I was a Reality Bites superfan. If a friend said they’d choose Ben Stiller over Ethan Hawke, I couldn’t so much as look at them again. The Free Winona movement was at the core of my being. At my Us Weekly interview just a few months earlier, I told them if I could interview anyone, it would be Ethan Hawke, though I couldn’t guarantee any semblance of professionalism if I did. Was that a manifestation of sorts? And more important, Universe, how could this be happening right now? It was beyond belief that the only person who cared about me, in the middle of all this crisis, was Ethan fucking Hawke.

I wanted to turn around and admire him so bad, but I was terrified to turn around too. I couldn’t look back at Chelsea Piers and what was now my past and all the chaos I had raised and all the innocence I had destroyed. They were probably just stomping on the glass and cheering, Mazel tov! at that very millisecond. I couldn’t look back. It was too shameful.

But, wait, that was seriously Ethan Hawke.

I had to turn around. Come on, I had to. So, I stopped. I wiped my eyes. I put my boob away. I turned my body around … and I swear to God, at that exact moment, Ethan stopped and turned around too. And there we were: me, the deranged lunatic, and him, my Dream Guy, as sexy and grungy as I imagined he’d be, staring at each other under the most flickering, soul-warming New York City sun.

Finally the spinning world stood still. My mind stood still. My naked feet were planted firmly into the earth. Ethan’s earth. And then, he smiled. A real, honest-to-goodness human smile that seemed to come from the depths of his being. A friendship smile. And I couldn’t help but smile, with all my bruises, with all my heart, right back.

It was an extraordinarily glorious moment in my life. Not just because my celebrity crush was right there lifting me up when I needed it most—although, amazing encounters like that are why I believe in a higher power. It was because this was the catalyzing moment in which I knew I was not a dangerous person. I was just different. And I would stay different. And I would embrace different.

Everything was about to change. I was leaving a world where I would only burn things down, and walking toward a life where I’d actually, eventually, convivially escalate lovers and friends and strangers. It was going to be crushing and thrilling and confusing, and perhaps I’d have to sacrifice having lots of babies and any money and the comforts and touchstones that wise women like my mother genuinely believed mattered. Any chance of a nice and normal life was abandoned that afternoon at Chelsea Piers, scattered in the calla lilies, sprinkled on the salade Niçoise, smashed on by Cole Haan loafers during the horah.

Heartbreak would find me all over the world and I would never be anyone’s beloved again—not like that. There was no turning back now, and though that put me on a long and lawless path alone, I never doubted for one second my decision to go romantically rogue. But what exactly was awaiting me? It wasn’t a fairy tale. But it was the opposite of choking.

Before our soul-whispering smiles lingered on too long, Ethan and I turned around and went our separate ways. But I had the answer to his question: I will be okay. I will be okay. I will be okay.

two

See Alyssa Date

He was a doctor who liked to play doctor, and I was contractually obligated to go out with him.

Let me explain.

A few years after I broke off my first engagement, Glamour magazine hired me to write one of the first ever love blogs in magazineland: See Alyssa Date. This was back in the day when Anna Wintour, over at Vogue, was still processing the word blog and wondering why it sounded so vulgar, and I couldn’t help but agree.

Word on the street was that dozens of young female journalists wanted the love blog position, so without fully researching what the column actually entailed, I immediately accepted the offer, blinded by the ego of it all. How cool! They chose me! Glamour was so glossy and influential; I felt like I had snuck into a whole new league. And it’s not like the material was out of my reach or anything. I was a libidinous, tempestuous, and rebellious twenty-nine-year-old writer who had just moved to LA to live my best life. But, in hindsight, I was also overeager enough to say yes to the gig so quickly and erroneously.

The way the column—which I later learned was interactive—worked was that I would post a few paragraphs about my love life each day, and then end each mini-saga with a question for the readers to vote on. For example, Knowing I want kids someday, should I continue dating the Texan with no testicles? Or, Can I really trust a man with a kitty named Pussy? PS Please consider the fact that I am allergic to cats. Or, Do we all agree that Rob the Slob has one too many red flags? The Internet Gods then tallied the readers’ votes, and I was meant to obey whatever the majority instructed me to do, and report back with details. If the readers wanted me to give the dude with the three DUIs another chance, I’d have a peppermint tea in Santa Monica with him. If the readers believed I should be open-minded about the creepy cardiologist, I would give it the old college try. Did I do everything they said? For the most part, I did. Did I enjoy any of it? No, I did