© 2016 Caitlin Rain Rainy Day Drawings

I arrived at the hotel just after 10 pm. The lobby was brimming with 20-somethings in branded t-shirts tucked into pencil skirts, probably. They wore nametags slipped into nametag holders attached to lanyards, probably. They were probably putting away, by that point, their second glass of pinot grigio. Four-thousand of my closest work friends, these people were.

At the entrance, I rooted around in my bag for sunglasses or a hat or a stick-on mustache. Sunglasses would do. I ducked down, pushed through the revolving door with my forearm and swept through the lobby and up to the front desk in one continuous motion.

I didn’t claim victory until later, when I reached room 418 having said hello to no one.

The next day, I met four friends for lunch in the banquet hall. The tables were draped in white polyester and erected at their centers were cards designating which teachers were meant to sit where. There were tables for English teachers, for math teachers, for elementary teachers, and so on. There was no such designation for us, a bunch of over-the-hill-at-32 hangers-on who show up at these things for nominal speaking fees and free food and drink.

We found a table on the periphery intended for school psychologists. Cole plucked the card from its stand, turned it inside out, scribbled “VIP,” and replaced it. It was a brilliant, economical move, we all thought. Those three letters announced our rightful status and, more importantly, guaranteed our safety from the hordes of strangers and, worse, professional acquaintances who might otherwise want to join us. We’re the kind of introverts who don’t mind addressing an audience of 500 but do very much mind making small talk with strangers while sawing into herb-encrusted chicken breasts and drinking from goblets of immoderately iced water that, on that basis, smacks you in the face every time you take a sip. Our self-designated VIP status reflected some salient features of my personality, I thought (I won’t implicate the rest of them): misanthropy, self-importance, and introversion. Looking at this list of salient features now, I can’t help but wonder if it isn’t a bit redundant.


I’ve always felt that claims about personality—whether in the form of internet quiz results, drunken late-night ramblings, or the manager of TGI Fridays telling me I’m not cut out for the food service industry—were just a notch realer than horoscopes. Recently, Jay told me that even psychology research suggests that contextual factors dwarf the influence of any stable set of traits we might call personality. Still, I do nothing if not trot around the city proclaiming my introversion, sidling up to people having a terrible time at parties and finding a way to ask if they, like me, self-identify as introverts. What could be so appealing about the introvert designation that I’m willing to embrace these essentialist ways of thinking just to claim it as my own?

I’ve attributed to introversion everything from my tolerance for repetition (songs, TV shows) to my sense of grandiosity to my bad grades (high school) to my good grades (college) to my love of sitting down to my lack of Saturday night plans to my meticulous planning to my hunch that I’d be good at the drums to my tendency to hold forth to my tendency to say nothing to my lack of any sense of direction to my powers of observation to my absentmindedness. There are plenty of think pieces and TED talks (and more than a few internet quizzes) that explain how introverts are not necessarily shy and don’t necessarily have social anxiety, so I won’t bother laying out the evidence here. I’ll just say that we introverts are oriented inward.

If we can’t find the exit in the Bed Bath & Beyond, for example, it’s not that we’d prefer moving in to the Bed Bath & Beyond to asking someone for help. It’s just that we’d consider moving in to the Bed Bath & Beyond before it would occur to us to ask for help. It’s also that we very well might envision the life we would make for ourselves in the Bed Bath & Beyond, imagining how we’d make a pillow fort to live in, complete with an air mattress, a lamp, a mini-fridge, and a George Forman grill—and an alarm clock so we could wake up in time each morning to disassemble it. (OK, I’m almost done: We might also imagine how, like Natalie Portman in that one movie, we’d keep a log of what we owe Bed Bath & Beyond and find a way to compensate them for whatever we used.)


In contrast, most of my exes—notably, Jay and Two—are oriented outward. They’re classic extroverts. They make as many friends and enemies walking from the 1 train home as I’ve made in my entire life. On the plus side, these totally inexplicable investments in people they don’t know usually lasted long enough for me to quietly steal their wallet.

These extroverts can’t stomach doing just one thing. They always want more and more. If you watch a movie with Jay, he’ll pause it in the middle of a scene to show you a related YouTube video and then pause the YouTube video to tell you a related story.

Meanwhile, Two couldn’t simply eat at a restaurant. He needed a garrulous Sardinian bartender and a wall full of liquor to quiz him about. That’s why he insisted on eating at the bar. I always assumed that he needed more and more to distract himself from the sinking feeling that everything is nothing and that, no matter how many handmade shoes one buys or how many pisco sours one drinks, we’ll all wind up dead one day anyway.

I don’t know. Do I call myself an introvert because it gives me license to act weird and quiet when I feel like it, because apparently it gives me license to be whatever I claim to be?

It could be that. Or it could be what we five learned that day in the hotel banquet hall: that absent any other suitable category, we are the people who invent one of our own. Then again, maybe that’s just the misanthropy and self-importance—the introversion—talking.

Then again…


Breakup Advice

A very wise person on the internet once said, “A relationship is an expensive way to watch someone like you less and less.” It follows, then, that a breakup is a cheap way of liking yourself more and more.

As a person who has been left by many men, I have developed some expertise in the art of overcoming a breakup and, in doing so, liking yourself more and more. I share it with you in flow chart form. Happy breaking up!

Relationship Advice

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October 2015

I’ve always thought that Two and I were at our best in extreme weather.

The Heat

When it was hot out, Two would leave first thing for a three-hour run. While he was gone, I’d sit in front of the AC unit and text him links to websites that explained how he’d probably die running in such extreme heat.

I’d inspect my mosquito bites from the night before. Without him there to scold me, I’d scratch them until they bled. When he’d return, I’d act normal, tucking my legs up under me so he wouldn’t see the welts. He’d give me a cool, salty kiss and head for the shower. I’d resume scratching.

Later, we’d set out for the beach. He’d grab his bike and find me some janky old one with the seat set way too high. My eyes, blinking from the sting of sweat and sunscreen, were useless. I’d have to pedal along toward the sound of his voice, which I could occasionally make out over the clanging of the bike chain.

He loved lying about how far we had to go. “Just another three miles,” he’d call back to me. And I’d groan and drop all my weight onto the pedal, swerving probably into the beach traffic, but who knows. By the time I righted myself, he’d already be standing there near a patch of reeds, dismounted, laughing at me.

One time in Argentina, it was too hot to do anything other than pose for photos in my silk sundress. In one, I scowled at a catcaller. In another, I stood in front of a statue of Pope Francis, his hand outstretched. Two arranged the photo so it would look like the pope was touching my boob. That one was his favorite. Lucky for me, he got his kicks just threatening to post it on Facebook and didn’t actually do it.

That afternoon, we stopped for a drink at a sidewalk cafe. I left him with my stuff for a few minutes to go see about a restroom. When I returned–quietly and from behind–I caught him scrolling through the dozens of selfies he had apparently taken on my phone in the few minutes I was away. He was just testing the camera, was his defense.  

I won that round of our ongoing game of “Who’s less vain?” But when we got up to leave, my victory was subverted when Two observed that I had sweat through the back of my dress. It’s hard to feel like a winner with a visibly sweaty ass.

The Cold

Two knows how to dress for the cold. The man loves his knitwear. In the winter, we’d squeeze into the entranceway of his apartment to suit up. He’d try out several hat-scarf combinations before settling on the same one every time. “This hat’s kind of interesting, no? No?” We’d prop ourselves up on each other as we pulled our boots on. He’d warn me that I needed a hat, scarf, gloves, a heavier coat. He’d offer me one of his, a formless olive green thing, and I’d reject it on the obvious grounds of not wanting to look formless and olive green.

Outside, predictably, my ears would redden in the cold, and, at each corner, as we waited for the light to turn, he’d cup his hands over them to keep them warm. If he got bored, he’d kiss me.

Once, a blizzard grounded us for three days. The city shut down public transit, so I couldn’t get home. Before the worst of it, he took me to Citarella to stock up on blizzard provisions. Typical stuff: Marcona almonds, burrata, anchovies. He dragged me from cobbler to cobbler to find the right mink oil to protect my new Christmas boots from the coming storm. The man knows how to protect his leather goods. I dragged him from shop to shop to find some fresh underwear for the next day.

That night, we wound up at a shitty bar with his friends. It was just dark enough and everyone was just drunk enough for me to get away with slumping down in the booth, resting my head on Two’s shoulder, and just watching the night happen.

We didn’t know how long the snow had been falling when we reemerged into the night. Charles Street was empty. All distinctions were neutralized by the snow. The four or five of us rollicked through the void until Two slipped on a stretch of ice and pulled me down with him. Rolling around on the icy sidewalk, I wanted to laugh the way drunk people do when they fall, but my urge to laugh was offset by my need to pee, the way drunk people do at the end of the night. So I stiffened my body to avoid disaster, which is all one can do in such a situation. But just as one should never stiffen one’s body in the unlikely event of a bear attack–lest one make oneself easier to maul–one should never stiffen one’s body when Two is groping in the dark for something solid to lean on as he tries to stand on ice.

There we were, in the cold, caught in a web of our own contradictory urges. Meanwhile, down the street at his apartment, the almonds and the anchovies, the mink oil and the new underwear sat in silence in a pile of bags on his kitchen counter.

The Advice

I’m supposed to use this post for relationship advice, so here it is:

There will be a moment in every relationship when you’ll learn if the person sitting across the table from you can bear being human, or if they are so repulsed by their own vulnerability that they can be nothing but repulsed by yours.

Don’t worry about that moment until it comes. Don’t wait for it. You’ll go mad. No. Just bundle up and buy some anchovies and mink oil. Sit in front of the AC and scratch your bites until they bleed. Put your head on his shoulder. Pose for the photo. Pedal along.

But when that moment does come, as inevitably it will, and you can see that the person sitting across the table from you hates darkness, complexity, himself, and you: leave.

Either that or move to an extreme climate where you’ll be too uncomfortable to notice the difference.

How to Make Ravioli

Last week, I was asked to teach some of the loveliest people I know how to make pasta. There was some confusion over the meaning of “making pasta,” and, long story short, I wound up showing them how to fry up eggplant, smash tomatoes, tear mozzarella, and stir it all into preexisting pasta.

So, this morning, my mom and I made some ravioli, and I made a little pictorial tutorial out of it. Here’s how we did it:



Me and Two


April 2015

For our fourth date, I met Two in Port-au-Prince. I decided for sure that he wasn’t a murderer when I spotted him through the glass partition at baggage claim, waving at me, smiling stupidly, and generally looking like a bucket of puppies.

When people ask about our fourth date in Haiti, I tell them about our one-armed bodyguard and the pistol he tossed on the front seat of the SUV like it was a pack of Fruit Roll-Ups. I tell them about the drive across the Haitian countryside and about the weirdly strong cell signal we had out there. I tell them about how we huddled around my phone in the backseat and streamed a clip of Rhiannon talking to CNN about the video of her pit bull that had recently gone viral. I tell them about the stop we made halfway through, about the way the guard took me by the elbow and led me into the market, parting the schoolchildren who were pointing and grinning and reaching for my hair.

These are the stories I tell, but in the privacy of my memory, it was just me and Two, drinking beer on the beach, swapping stories about horrible people we’ve known.


A month later, I would be sitting on the edge of Two’s bed sobbing into my hands. It wasn’t really about the joke he’d made at my expense. It was about the why are you escalating?’s and the you’re overreacting’s and the come on, man’s that had been parading out of his mouth for an hour. 

In that moment, I could see the whole relationship unfold before me: his passive-aggressive jokes; my retreat into daydreams; his retreat into his phone; the fights that were not really about the chicken or the avocado or the book that, yes, was thrown but not thrown at him; my waiting, my waiting; all the chances we’d give each other; all of the poetry and platitudes I’d summon to rationalize those chances; the way I’d tear at the edges of my cocktail napkin when I told my friends we wouldn’t be breaking up after all; the way they’d take a slow sip before responding, “As long as you’re happy.”

I wasn’t crying about the joke. I was crying because, in that moment and in every moment of conflict since, I was experiencing the whole long, painful end of me and Two. (I guess I’m the Mozart of lots of things.)

The next morning, blinking into the flat light of early winter, we resolved to think of the whole episode as, let’s say, aberrational. As things tend to, the relationship kept going, and, as people tend to, he kept being the same.

But something else happened. As we traveled through Argentina and then later to Oaxaca, threw dinner parties together, attended his cousin’s bat mitzvah, Two became funnier and more specific. He looked handsomer every day with that down-turned mouth of his, that upturned posture. Our banter became more precise and brisker.

And, all of a sudden, we could claim for ourselves shared memories from our halcyon early days. When he didn’t laugh at the excellent joke I made about his sneeze (“That was a classic of the genre!”). When we realized that two of the horrible people we had told stories about were actually the same person. When I waited on a bench outside the American Embassy while he went looking for the laptop he’d left on a bus, and I, only somewhat irrationally concerned for his safety, steeled myself to intervene and rescue him. We’d reminisce, correct each other’s versions of the stories, and proclaim, with only the most tenuous logic, that what the other said or did was just so hilariously typical.

And all of this–all of this business that, I suppose, is about falling in love and remaining in love–only made the fact that he wouldn’t change, and that I wouldn’t, that much more painful.


In our photos from Haiti, the blue is the bluest blue, and the green is the greenest green. The sky, land, sand, and sea are brimming with their proper colors. In those photos, the world looks so straightforward. I’m jealous of the person I was, the person who got to sit in that world for a while, the person who thought the worst thing about Two was that he didn’t know how to pronounce Beyonce.

Now we are the horrible people we tell stories about. And this world looks like the one I see in a portrait of him I once found tucked away in a bin with old mail and receipts. His ex had painted it. This world looks like thick, complicated strokes of muted color. It looks like Two, walking away.

Optical Illusion


January 2015, Buenos Aires

He has eyes like the sky in winter. He smells like two hundred dollars’ worth of bath products you buy in a store decorated with dead leaves and a canoe. His legs are uncompromising, like trees or fortresses. He says words like aberrational and sublimate like other people say want to see a movie? and don’t forget the eggs. In the morning, he crawls up close while I’m sleeping, puts his mouth right up to my ear, and yells, “Mr. Pickles!”

I’m in Argentina with a stranger. He’s my boyfriend. I’m in Argentina with Two.

He thinks he made pesto last night, but he did not make pesto.

He runs three hours every morning. What he never says when he comes home panting and red-faced is that he stops to eat pastries and make friends along the way.


I don’t understand Two. I mean that as a statement of fact, not as commentary. I look at him across the table every night, searchingly. I study him as I’d study an optical illusion. In the optical illusion, I can only ever see the young woman, never the old woman. And those squares look like such different colors to me, even as I learn they’re the same. The vase I can kind of see, but I can’t hold it in my mind for more than a second or two before it morphs back into two silhouettes. How does one come to understand the person sitting across the table?


He asks the cab driver to take him to the cueva, which is Spanish slang only he knows for a place to exchange money at the street rate. He thinks I close the cab door too hard. He thinks it and says it and says it and says it. He changes his mind about the restaurant mid-stride. He asks to eat at the bar.

Wisps of gray hair are starting to curl up under his ears. He looks like a founding father. He says he looks like Graydon Carter. He doesn’t understand why the founding father thing is funnier.

He thinks my favorite phrase is “I don’t know what to tell you.” What he doesn’t realize is that he always says whatever he’s saying many times in a row.

He can’t believe I never read that book. He can’t believe I never ate that food. “Reeeally?” he asks.

He speaks English like it’s his second language to people for whom English is actually their second language. “The bar is called Rosario. Is near to here, no?” He either means to or doesn’t mean to. It’s one or the other.

He purses his lips when he doesn’t have anything nice to say. He speaks in a voice like suede when he does.


The thing about an optical illusion is that when you start out looking at it one way, it’s hard to ever see it any other way. You unfocus and refocus. You tilt your head. You look away and look back.

Our brains want to organize stimuli into meaningful information–at least, that’s what I read. That’s why we tend to keep seeing optical illusions the way we saw them initially. That’s what makes it hard.

It feels radical, dangerous even, to let go of our structures of seeing, to allow those data points to blur and then sharpen again into a new image, a fuller image. I think I see Two sometimes. I think I understand why Graydon Carter is funnier to him, why he can’t stand the sound of the cab door slamming shut, why he can never choose a restaurant. I think I see him, but I stop trying for one second, and he’s gone again.


He wants to go to a diner in Koreatown in the middle of the night. If I say no, he’ll make himself pasta e fagioli and smoke weed while I sleep.

He wants more salt, more spice, less light, more room, better wine, warmer days, longer nights. He wants more me, less me. He wants it all.

He’s the strangest thing I’ve ever seen, as he runs out into the freezing-cold ocean and calls out for me.

The Mozart of Bitterness


September 2014

One evening, late this summer, I declared myself the Mozart of Bitterness. I was sitting neatly on the end of the couch that doesn’t get sat on. It was one way to be less hot. I felt high up, tilted. My legs dangled. I had opened the window too, but it was of no use. The air wasn’t moving.

My elementary music teacher Mrs. Jackson wore long cotton dresses with sneakers. During her first divorce from Mr. Jackson, she taught us to sing “I’m Gonna Wash That Man Right Outa My Hair,” which, in retrospect, was weird. The other thing I remember about her is that she told us that Mozart could hear in his mind’s ear an entire symphony in a single moment. Every beat, phrase, and measure, from the allegro to the adagio to the rondo. His mind could collapse it all into just one second. It was then only a matter of unfurling his masterpiece and bringing it to the page. This was the nature of his genius.

No one on the internet wants any part of this story, so I guess it was just another one of Mrs. Jackson’s pedagogical flourishes. That didn’t stop me from declaring myself the Mozart of Bitterness that evening, late this summer.

I spot a name in my inbox, and, in a single moment, I can conjure every wrong ever committed by the possessor of that name. I relive the pain of that time she stood me up at that one coffee shop with the fruit-free scones; that time she was thumbing through a stack of cropped pants at J. Crew and, just for my benefit, sighed, “I suppose I’m up to a size 6 now”; that time at the party in that warehouse when she gave me the look that I know meant I was talking too much about my ex and, further, that I’m a self-involved person generally and lucky to have anyone who’ll listen to me carry on at all. Yes, I can experience all of that in a single moment.

To be clear, my bitterness is not reserved for any one person in particular. It’s for anyone. It’s for everyone. And I conjure wrongs both big and small, both real and imagined. I relive them all.

This is the nature of my genius.


The Mozart of Bitterness. I chuckled at the thought in spite of myself. I’ve been depressed.

While I’ve always had the trappings of depression–extreme introspection, a tendency to leave rooms suddenly, a personal narrative blog–only recently did I start feeling depressed. Years ago, after my then-fiance summarily dumped me over the phone, my therapist suggested that I let myself feel sad. I tried to convince him that I simply didn’t know how.

“I don’t own sweatpants, and I don’t listen to Bon Iver,” I said.

“I can’t eat whole pints of Ben & Jerry’s. I’m lactose intolerant,” I said.

“I like Beyonce and pizza and jokes,” I said.

It seemed that grieving would be so much easier for me if only I knew how to feel sad. I dreamed that one day I would develop the depth of emotion and character to fully experience loss, to sit with it, to just be with it.

I’m here to tell you that dreams really do come true. Five years on, I’m not just an expert at experiencing loss. I’m a virtuoso. After all, I’ve managed to achieve this state of grinding hopelessness and despair in response to the most ordinary of disappointments. Friends of mine are divorcing, breaking up, falling out with me or with each other. It’s true that I’ve had my share of medical trouble, but, if anything, cancer wound up being a good excuse to start a blog and a great way to get people to show up to my birthday party. I don’t know how I got this way, but at some point in the past few months, life started to feel like nothing but an accumulation of burdens.

To wit, my mind can twist a monosyllabic text message into a grievous offense, a routine interaction with a customer service agent into a referendum on her character, a friend’s suggestion to keep a gratitude journal into cause for a 2,000-word e-mail laying out a critique of the neoliberal sham we call positive psychology.  

My imagination, once applied to daydreaming about being surprisingly good at karaoke or delivering stirring speeches before an audience that happens to include everyone I’ve ever wanted to impress, is now used to stretch my capacity to be cruel. I use my imagination to develop and refine diatribes, rants, condemnations, denunciations to suit all occasions and tastes. I select and arrange words in ways ever more punishing to their imagined target. In my daydreams, I’ve become as sharp-tongued as I was inspirational. I am, no doubt, the Mozart of Bitterness.

December 2014

Three months ago, I wrote that I was the Mozart of Bitterness. I liked the idea. It felt very me, but I couldn’t figure out where the piece was going. It needed a turn of some sort–a sign of hope. I wanted it to end with a breeze that felt just right on my forearm or a bit of sunlight breaking through the tree branches. I waited for the turn to come.

But as it happened, my life turned in the most utterly ordinary way. I was suddenly no longer depressed, and it was because of nothing grander or more poetic than 50 mg of Zoloft a day and a new boyfriend. It’s a hard thing for me to admit. I just hate to be so basic.