The Business of Dating

Hi Divas and divettes.

This is probably a prickly thing to share on a blog, but the backbone of the Hot Literati brand was built off of me blogging about clubbing and dating, so I figure it's time to return to my roots. I've always said that I think the best writing is honest writing. So much so that I have "be honest" tattooed on my left wrist.

"Have fun" is underneath "be honest."

I feel that I'm getting so much advice, warranted and unwarranted on my artistic life and professional life.

Some people in my corner are trying to get me to fundraise, which would mean giving away part of my company (and the Hot Literati brand) in turn for capital to help it grow faster. To be very clear, fundraising would make my life a lot simpler in the short term. I would pay myself a pretty normal salary and be able to spend more on getting the word of the brand out there.

But in my mind, the end goal is to create more Hot Literatis which can also be done word of mouth. And that brings my mind back to when we held a scavenger hunt in Washington Square Park and these sweet 19 year old girls told me they paid for our Substack and even had their professor analyze one of my essays in there class.

I guess my problem is that I like to skip to the end of things, like reading the last page of a book before reading through the full story. And if the end goal of fundraising is to get more Hot Literatis in the world, then to that I say , share it with your friends and do the scavenger huts in the latest launch together and submit your writing and art. Right? But maybe I'm naive. I probably am, but like Myshkin in The Idiot, I think naiveté can be a great skill sometimes. What do you think?

So, Instead of confronting the very real, very imminent questions, I am going to -- for the girls -- give you all a brief history of my dating history and how it led me to entrepreneurship.

I saw Isabel Timerman (?) post about how she wasn't afraid to overshare on the Internet and now she's publishing a book of essays. I, happily identified as a crazy woman with my peers, am not afraid of anything but God.

So instead of money we're going to talk about men, with a little loose advice woven throughout for the teenage girls reading the blog :*

MIDDLE SCHOOL

I wasn't allowed to date until I was sixteen, so of course a boyfriend became like this magical thing to me. I thought it would be everything like the movies. And then I had one at 13, even though I wasn't allowed to. There was this big special eighth grade dance and I missed it for ballet and he danced with another girl and broke up with me the next week. Cue the beginning of my trust issues.

HIGH SCHOOL

Fast forward to high school. I had lots of crushes but none of them ever wanted me. And then I won Miss Kansas Teen USA and all of a sudden, some of them wanted me.

Then I had these funny, reticent flings. I went to the homecoming dance with a French foreign exchange student who lied to my father in our living room, telling him that he believed in Jesus Christ. As he drove me from the restaurant to the school, he looked at me in a borrowed sports car on the highway and admitted that was a little more existential. We had fun, he slowed danced with me to all the songs, even the fast ones. But I ghosted him a few weeks later. It would take me a long time to learn how to not ghost people.

A little while later, I had a fling with this sweet guy who would drive around three hours to spend the day in town with me. He lived in a small town. We had our first date in Kansas City. I wore a tight, brown dress and I was so nervous. He took me prom, but I quickly found out that he was a kleptomaniac because he slipped some of the fake candles into his suit jacket. He was so tall and sort of looked liked Jimmy Stewart (who, fun fact, was in the same eating club as me at Princeton).

When I won Miss Teen USA, I remember him sending this message that said something like "I'm afraid I'm never going to see you again." And then, I'm not proud to say, I ghosted him. But that was a message that made me feel a certain type of way, you know? I can't describe it, but you get the feeling??

PRINCETON

So then, I'm Miss Teen USA and I'm about to go to Princeton. On and off all summer I'd been messaging this guy who grew up there and was going into the same year. He'd found me from the facebook group of incoming students and would send me these long, dreamy messages quoting all sorts of authors.

When I went to New York for my media week, he took me to a restuarant in the meatpacking district and then we kissed on the highline and snuck into the terrace of a hotel to finish the bottle of wine he'd been keeping in his backpack.

He had to go back to Princeton that night, but at some point I remember him trying to convince me to let him come up to the Miss Universe Apartment. I was such a goody, there was no way I was doing that. But a few days later, I took the train to Princeton and we got crossed in Prospect Garden. Meandered down to the train tracks and saw a deer.

We stayed up all night, but the next morning I couldn't stop crying. I felt defiled, even though we didn't... you know? I cried the entire train ride back. I probably scared the living daylights out of him. Moreso when I got to campus and saw him having coffee with a girl who looked a lot me. I remember showing up at his door one night very drunk and very sad as his roommate, who was very cute, actually, looked at me sleepy and confused. I was such a mess.

But even among the mess, I was extremely ambiitous and very passionate. I always wanted to do things authentically and in my own way. Like in high school, I forgot to tell you guys about my first boyfriend. How did I forget that ???? I was sixteen. He wrestled and was a little younger than me. A couple months or so. He went to a different school and I can't remember when or why we broke up, I just remember crying before ballet class the next day or the day of. But a little while after, he sent me this really beautiful message on Twitter about how I changed him. Made him get more serious about his own life. I think about him sometimes and I hope he's doing well.

And then before Princeton, I briefly had a fling with the quarterback. We would sit in his Dodge Charger as he'd play 21 Savage. He always smelled like smoke, but he was SO handsome. I remember flat out telling him it wasn't going to work because I was too ambitious. He sent me a DM a year or two ago after one of my videos went very viral.

So back to Princeton. I eventually met my college boyfriend. He played basketball and also loves Dostoevsky. We were together for four really peaceful, dreamy years, until it ended in a mutual but very painful way. But that was my first real love, you know? It was so pure in a way I've never experienced before. I remember when we were on a trip to California with his family and we stood at the edge of a Pier. He's the person who started calling me "hailo." And we looked over the water and he looked at me and said "Man hailo. If you fell in, I'd have to jump in after you." And I think in that moment, I understood what love was. We lived in Germany for a few months together, but I had to get on pursuing my own dreams on my own terms.

New York

New York is really the wild west, you know. And I dove in head first. I was clubbing a lot with friends who clubbed and the first person I had a thing with was a man in his 40s who'd just sold a tech company for around over a billion. I liked him, but I was so heartbroken and I didn't really know how to date or do literally anything. I didn't even have a job yet, I was sleeping on my friend's couch in Bushwick.

I remember standing in his apartment as he poured me a glass of Gin and said "You're an Ivy League grad without a job," and he sounded very entertained. But even then, I always knew I was going to do something, you know? And I had such a clear sense of self and purpose that I wasn't really phased or surprised by anything and by the time I left I'd forced him to order a Kurt Vonnegut Novel that I hope he's read by now. I see him around sometimes and I still get red.

I had an on again off again thing with a few people for years. Even though I eventually learned how not to ghost, I was very bad at ending things. Some of my favorites I've already written about. Others I haven't.

Like the formerly Vine famous business owner who'd let me come over and cook at his apartment when I was really depressed. He was so great, but he wanted a wife that would just sit at home and be normal and that wasn't me which sort of hurt.

Or the British artist I was so in love with who just didn't know how to be faithful, even though I was so in love with his art because he was and is brilliant.

Or the tech founder who few to Paris for me, with matching tattoos we'd gotten unbeknownst to one another. Gosh.

I guess one story I haven't told too is the story of my first open mic in New York. I was so lost (emotionally), running a lot every day and I tried to jog to this new library but got lost (literally). He saw I was wearing a Princeton sweatshirt and asked if I'd gone there. I said yes. He had too, but he'd gotten sent away, I think.

He was very tall and very handsome and very Dominican. We exchanged Instagrams, but I didn't think much of it, until I passed him a couple of hours later in Washington Square Park. I pretended I didn't see him, but he got up and playfully accused me of following him. I laughed. He asked what I was doing later and I told him I was going to an open mic. I was so nervous.

I went home and printed out my sheet music and messaged him the venue on Instagram. He met me there. As I sat, being afraid of forgetting the words and reflecting on the song I was going to sing, Last Two Dollars by Johnny Taylor (my late Granny's favorite), he whispered in my ear that I was the most beautiful girl in the room, in the whole world, and that I was going to be great.

Afterwards we went downtown. He took pictures of me in the train station, of us, and then we sat at the basketball court off Bowery, sharing life stories. He put me on his shoulders and walked me around the sidewalk. "I know that's right" women yelled at us outside of the club.

I saw him months later, a few weeks after the tech founder had flown to Paris for me. By that time he, the founder, was my boyfriend (he isn't anymore). The Dominican guy crossed the sidewalk, smiling at me. "I was just thinking about you," he said, "It's been a while since I've had a conversation with someone smart."

I guess my last and best story happened when I was twenty-four. A guy smiled at me from his car on Canal Street as I was jogging, and then a minute or two later after I crossed the street he was right there in front of me. He'd stopped his car and left in runnning in traffic to come out and get my number. We had dinner and drinks. I drank a lot back then. The next morning I'd gone on a run and he called me bright and early and simply said "You're a genius" on the phone.

He was great, but I was much too young and insecure and I wasn't ready for anything serious. I actually ran into him a few months ago.

"8 million people in New York and I run into you," he said.

I have a pretty deep appreciation for him because on our first date, he looked at me and said "You are an entrepreneur. You're going to figure it out. And it's ok if you don't, because you don't have to."

So yeah.

I've dated a lot of people. Most casually and inconsequentially, but I think the thing I've always been looking for is for someone to hold me and say it's going to be okay. Or for someone to look out over a body of water and to say that they'll come get me if I fall in.

But my problem is that I've always wanted to walk on water and I've never believed that I couldn't, because I'm not afraid of storms. I'm only afraid of God. And you can't make a God out of people and I've tried not to make Gods of the people I've dated, but gosh throughout all of these experiences, I've always tried to see what they see in me and channel it into my work.

Sometimes I feel like the most intimate relationship I have is with the people who read my work and understand the thing I'm not able to put into words. And that's the thing about investors, I guess. You have to put something into words for them. But I feel like if you're here, then you get it. You get it and you should participate, right?

But I don't know. I really don't know. There is a reason that my favorite ending to any book I've ever read is This Side of Paradise. He leaves Princeton with this sense that he should be able to conquer the world, but all he says is "I know myself, but that is all."

xx

hailo