On playing the lottery

She’s so lucky she’s a star but she cry cry cries...

(timid) Hey..….

I’m sorry I haven’t posted here in a while… (lying) I’ve been busy… well, I’ve had a boyfriend, and I don’t know how other people pursue love and art simultaneously, but I find it hard. I’m always worried my vulnerability will give my lover the ick… a vulnerability some readers have called “shocking”... a vulnerability that implicates said partner… perhaps in a way that’s unfair? Or is this a cope? Am I insecure? Or just lazy? Shall we gloss over the fact that I’m more comfortable being vulnerable to strangers than a beloved trusting partner? Can we please? Needless to say, the relationship is no more … so… let’s all say welcome back, Olivia!

The breakup is Update #1. But let’s start from the beginning, from when I updated you last:

In August I went to South Carolina with my family. I came home on August 17th and got plastic surgery on the 20th - a chin implant and rhinoplasty - the latter procedure unbeknownst to everyone except for my boyfriend and roommate.

I spent my healing period alone, very alone. The solitude peaked my depression, as did getting really into The Smiths and painting paintings that are objectively and technically bad, and yet all I had at the time, so I would fantasize that they were good; I would fantasize about selling them for millions of dollars; I would fantasize that The Right Person would see them and inform me that I’m a genius

As soon as I finished antibiotics I started taking antidepressants.

The movie I starred in finally premiered after three years of (nonconsecutive) filming. The Paradise theatre on Bloor sold out (200+ people showed up!) and everyone was there - I introduced my boyfriend to my family. My mother sat him next to my father (“they can get to know each other!”) and side by side my boyfriend and dad watched me get raped on the big screen! (I didn’t get any sex scenes… just a few rape scenes….close enough!)

I was sober for three months and the experience was more transformative than the plastic surgery. The antidepressants helped, too.

The movie was featured at a film festival in Tucson, Arizona and I travelled there with the director to be part of it. I relapsed on a coronarita and don’t regret it. We got all dressed up and watched the film with just two other people in the theatre, one of whomst was sleeping. In our post-film Q&A (all of the questions, of course, asked by a moderator) I admitted (without prompt) which scenes I was high during

I found out that what I thought was swelling was actually a botched surgery. I got surgery again. I healed - less patiently - again.

I flew to British Columbia to meet my boyfriend’s family and then to Punta Cana with my own, where I had a bunch of precious jewelry stolen

My US working VISA got approved

My brother and sister got pregnant (with their separate, distinct partners, to be clear)

I performed at a few festivals, rebooted my podcast, gave up on my podcast, and started a part time nannying gig

I had my three month follow up to the second surgery (meaning I’m now more than half a year from the first one) and pointed out to the surgeon a gripe I’ve been too exhausted to honestly confront: the chin is still not centered. The surgeon told me he could do a third tweak, and though I want the chin to be perfect after all this time, pain, and money - I can’t even fathom going under again, taking more time off to heal, and letting this healing period stretch to nine months, to the better part of a year. I also just don’t really have time to do it before I move to New York, which I’m planning on doing in June.

I couldn't bring myself to berate him, per the suggestion of my craziest friends. Despite all of the botched procedures, I still like my surgeon. He’s a gentle and handsome man with kind eyes; kind eyes which clearly do not work

So instead of overtly blaming him, I tried to evoke a little sympathy (covertly blaming him) instead

I told him I couldn’t get any more time off from my nannying job

and he looked at me in a way that made me acutely aware of my error in judgement:

Pity - his kind eyes read pity.

Ugh. I forgot. I forgot that I am fucking thirty, and that Crying Broke isn’t cute anymore.

The surgeon didn’t know what to say. I guess he hadn’t considered that he had accepted so much money from a poor person, and now he was experiencing some combination of remorse and pity.

It made me think that there needs to be a department that determines eligibility based on income and mental well being before you engage in behaviours associated with addiction, like alcohol or gambling or plastic surgery. You should have to prove, somehow, that you aren’t an addict chasing your death drive; that you have or make 100x the money that you’re spending (like when you apply to rent an apartment) so as to not take advantage of addicts.

Such a bureaucracy wouldn’t inhibit me, btw, i'm actually literally fine! I’m rich and stable!! I only got the nannying gig to begin with because I had spare time and if I’m at a job making money, then I’m not out spending it (I also have a shopping addiction… can the government please for the love of God get involved?? )

Such a bureaucracy could never exist, though, because these industries all bank on the out of control remaining out of control

Nannying is another thing that isn’t cute at thirty. Instead of raising your own kids, or focusing on your own career so that you can one day afford to have kids, you’re watching another woman’s kids so that she can focus on her career.

When you’re a thirty year old nanny, the dad doesnt even try to fuck you, which is like, half the point of being a nanny. … to be a titillating presence…..hello???

But I never feel uglier than when I show up to nannying. It’s as if there’s a desexifying magnetic field that I cross when I walk through the door and even my glamorously worn designer bag becomes a battered and tacky looking fake

The kids don’t like me, either. Everytime I sit down to play with them, the older one forbids me from playing with any of the toys, “that’s mine” he tells me, when I pick up anything at all, ripping it from my hands.

One day, he outright declares that he doesn't want to play with me at all, he wants to play with mommy and in my head I was like …… ok…. well, mommy doesn't want to play with you, which is why she’s literally paying me to do it…. do you think *I* want to play with you…..? I’m getting paid, dumbass……

What these brats don’t know is that I am brattier. I am a former spoiled kid and a Sometimes Actress. Thrice a week I work for four hours a piece and I can barely handle it. Half the time I’m listening to podcasts and yet still I am groaning in agony, because I can’t fucking handle the easiest job anyone has ever had

I worry about my threshold for discomfort, my ability to “handle” regular work, should my creative pursuits not pan out. Because though I was spoiled, though I grew up privileged, it’s not the level of privilege that promises to take care of you for the rest of your life. It’s the kind that sets you up for inevitable disappointment

When I was younger, I found my various abject minimum wage jobs to be novel, even romantic. It’s the reality of pursuing art, I thought. Working all day at the bar, showing up exhausted to open mics, dreaming of where I’d be eight years down the line

CUT TO: Eight Years Later -

I have improved by a small margin and accomplished a few things, but I’m still doing minimum wage work and will be for the foreseeable future

I miss being five years younger and having success be expected, impending. Because the future is here, now, and I’m no longer content to live like I did five years ago, mostly because it scares me to think that in another five, it’ll still be the same. Five years of the Same is a harbinger of more Same to come. And so I hyperfocus on how to change things. I hyperfocus on money. The driving force of my life is no longer love or sex or fun, no, not since I turned 30 and started antidepressants and a teenager’s job. Now I just want money, like everybody else. I want to be rich, because to be rich in this society means being dignified, it means being safe.

So, I’ve been playing the lottery.

You know, in order to feel less pathetic?

One of the first things I said to my ex when we started dating was that I think playing the lottery is a red flag, because you’re investing in a delusion rather than in reality

Then, one day when I was down bad and hungover in a gas station, the cashier asked me if I “want lotto” and I looked up at him like he was God

“Yes,” I said, breathlessly, like this was divine intervention instead of a simple upsell. Then I walked out carrying my lotto 649 ticket, smiling like a fucking idiot

I sat in the car and Googled the draw prize. 30 million.

Thirty million dollars, I think, I can’t believe I’m about to have thirty million dollars…..though with the exchange rate, that’s closer to 20 million USD once I get to New York. I can work with that, I think, benevolently. I can’t stop smiling alone in silence, savouring my little secret: I’m fucking rich.

My passenger is still in the bathroom, and since I kind of have to go too, I walk around back and squat behind the building, laughing to myself that a multi-millionaire should be so unclassy

To be unclassy only heightens my mystique, I think, they’ll call me an eccentric!

I smile, standing up to see that I have pissed all over my Uggs. I thought I had angled away from them, but no worries, what’s a pair of Uggs to a motherfucker like me?

I still get back to the car before my passenger and when he finally joins me I have no choice but to accuse him of diarrhea. Then, to even the playing field, I shift to self-mockery. I tell him all about my lurid financial fantasy and together we laugh at the absurdity of my conviction that I should win something so improbable, something far less likely than becoming a millionaire on my own accord. When we’re done laughing, we unpause the podcast we were listening to and a couple of real millionaires babble on. I tune them out and return to my fantasy.

When I get back downtown, I go see my man, who’s in a mood because his laptop is processing at a glacial pace. I bring up the fact that I bought a lottery ticket and he teases me for sporting my own red flag

Then he helps me download the OLG app (which has been more shameful to have on my phone than Facetune and CoStar combined) and we scan my ticket together.

“Congratulations” it reads, “prize not yet available. See a merchant for more info”

We look at each other, mouths agape. I’ve won. I won the fucking lottery!!!!!!!!!!!! I become giddy, rolling around thrashing in his bed, giggling like a maniac.

He laughs at the juxtaposition: “me: broken laptop…. you: wins the lottery” I laugh more. I tell him I’ll buy him a new one. What’s a macbook pro to a motherfucker like me!!!????

As we tuck in for sleep, my fantasy turns to planning. You might think that I’d be too excited to sleep, but more than excitement, I feel the absence of anxiety. I feel swathed in the promise of financial security

I knew God made me buy this ticket for a reason, I think, and begin Googling one (and fuck it, two) bedroom apartments in New York City. I bookmark a few. I imagine decor, I imagine parties, I imagine my life. I can live alone in New York City! In a good neighbourhood! I can replace my stolen precious jewelry! I can quit my nannying job, like, tomorrow!!!!!!!

I can pursue stand up comedy full speed ahead!! I can hire a videographer to follow me to every show!!! I can hire someone to promote my shows and run my social media…. shit - I can hire a writing team to refine and punch up my material! I can have a writer’s room for my act! I can get more plastic surgery and always have my highlights freshly done and overnight become the best and most beautiful comedian alive!!!!!!!

Though…. inevitably people would find out about my staff, funded by my unearned fortune - a fund ickier than daddy’s money - and scoff.

Then they’d find out I had a pool growing up and double their contempt. Any credit or goodwill I have earned through years of actual hustle will be rescinded. Nobody will take me seriously as an artist. I will be publicly mocked, ridiculed; my name will become a public punchline. I will have no choice but to quit comedy and live a life of leisure

At which point I will still be expected to be happy. Then, too, my personal relationships will shift. There will be expectations hinted or explicated that I fund and/or donate to others’ whims and/or projects. Every time a bill comes I’ll be expected to pick it up. I’ll feel too guilty to ever not, but then also, I’ll resent it, wondering what I even meant to people at this point

I’ll also have to stop shoplifting, though even as a millionaire, I’ll feel a moral quandary around spending $13 on eggs

I notice that my heart is beating fast, and no longer from excitement.

…

The next morning, I head right to Rabba to scan my ticket. My chest is tight, I guess I’m excited

“Congratulations!” it begins, “you have won another spin.” The cashier hands me my free ticket and I head to work

Before the kids get home, I cook and clean with my headphones in. I listen to all the comics in New York and LA talk about their lives, careers, upcoming show dates, and yearn to be amongst them. Every fifteen minutes the pod is paused for the same advertisement promoting a gambling app. I’ve memorized the jingle, against my will, as is the intention of jingles

I’m mad at myself for not being able to resist singing along. I’m mad that it’s even legal to promote gambling, especially in app form, to prey on the desperate and encourage delusions in an increasingly poor society, to make it so accessible, to couch one thing people are addicted to inside of another thing they are addicted to

I worry that after a certain amount of times hearing the same advertisement, I’ll succumb to it. If I see an ad enough times, I usually start wanting the thing being advertised. I’m weak-willed like that. I have been pressured into submission by many an ad; the psychological trickery seems to work on me.

After all, here I am with a lottery ticket in my pocket

I’m no longer fantasizing, though, the fantasy too quickly spirals into having to quit comedy, which makes me sad, sadder even than the notion of prolonged brokeness, of working minimum wage jobs deeper into my thirties.

The kids come home. The older one refuses to eat the dinner I’ve made, screaming that he wants a hot dog bun instead. Then, he goes over to the hot dog buns, rips open the packaging, tears them all up into pieces and throws them all around the kitchen, screaming “THEY’RE ALL BROKEN! WHY ARE THEY ALL BROKEN?!” and I’m amazed to learn how early men start gaslighting

He eclipses into hysteria, falling to his knees, scream-crying inconsolably about the broken buns. His little brother walks over and nonchalantly eats one of the broken buns off the floor, sending the older one sprinting across the room, smacking his two year old brother in the head, declaring that “{redacted} is eating all the buns and I don’t even have any!!!!! It’s not FAIR!!!!!!”

Eventually, the kerfuffle summons their father who puts the perp of HotDogGate in his room for a time out.

Now it’s just me and the little one, who’s still crying.

And me? I’m having trouble suppressing my laughter. I laugh at my dumb life and soon enough the shift is over. I head home and work on my shitty painting and when ten p.m. comes, I scan my lottery ticket and it tells me “Sorry! Please play again” and I am relieved, because I know that I won’t