Dating Tips for the Unemployed and Unsuccessful

Illustration: Superman by Eric Fischl, Sag Harbor, oil on glassine, 1978.
Dating Tips for the Unemployed is an excerpt from Iris Smyles's 2016 novel of the same name.

You are unemployed, at best very unsuccessful. Yet you go to parties. Parties where you meet people who ask, “So what do you do?”

You live with your parents. You share a one-bedroom with three roommates. You consider ramen a food group. You update your Facebook profile daily.

Your job has no title. You work within a department. You’re an unpaid intern. You’re assistant to the intern.

You stop people on the street and ask them if they like comedy, then push ticket packages to the “best comedy club in New York!” You stop them and say, “Excuse me, may I ask you a question about your hair?” You hand out free soap samples; nobody wants your soap samples.

You don’t read the newspaper; it’s expensive and the news is never good. Instead, you pick up the free alternative weekly. You skip straight to the comics and read without laughing. You could do better, you think. That is, if you drew. You blame your parents for not recognizing and encouraging your artistic potential early on. You remember when you were ten, you’d sketched some pretty realistic-looking horses. You skip to your horoscope: “Inside you is an untapped power source, Pisces. Tomorrow, Libra, a great opportunity will present itself. Be prepared, Gemini, the rest of your life is about to begin. Leo, stop living in the past, the future is right in front of you!” You throw the paper away before you get home and forgive your parents for not buying you pastels—they did their best.

You call your mom, and she asks you about the weather. You lie and say it’s colder than it is. You want to say something interesting. “We’ve a wintry mix today, Mom.” When she says, “You sound depressed,” you say you got a flu shot yesterday, just as she instructed, that it might have infected you. You feel so tired all the time lately. “Wear a hat,” she says.

“I’m wearing one right now, Mom!”

“Hold on, I’m going to put your father on.”

“Drink plenty of liquids,” he says. “And cheer up!” he commands, before hanging up.

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You take a job answering phones in a husky voice. It was funny at first, and all your girlfriends had a good laugh. You told them, “I’m going to learn what men want and then share it ALL with you!” After your first day, you met them for cocktails and they asked you what you found out. “Men want sex,” you said, too demoralized to go into detail. The reality wasn’t nearly as funny as the idea. “They never call in to talk about art or politics,” you joked. But no one laughed, something about your tone. You lie and tell your parents you’re a cold caller for the Ballet at Lincoln Center. You tell them all your friends are jealous because they let you work from home; you say, “A commission is even better than a salary, Mom!”

You log on to Facebook and update “favorite movies.” You take out Rocky. Put it back in. Then take it out. Then you add Rocky I, II, V, IV, VI, and III in that order. “Rocky IV gets priority and could switch places with V, though V is actually a superior film, as IV has a sociohistorical significance and represents in many ways the apotheosis of the Cold War experience in America,” you’ve been known to say on first dates. “You will lose,” you once said in an Ivan Drago accent, to a guy just before he kissed you, before he didn’t call you back.

You log on to Facebook and scroll down your ex’s wall.

Your college internship comes up at Thanksgiving dinner. Your mother says, “Why don’t you apply there, honey?” You can’t tell her that you’ve dated everyone in the office, that you can’t possibly go back now, what with Jed, Field, Gibb, and Markus all over the place. You’re too pretty or too easy, have low self-esteem or a superiority complex—you’re not sure what’s wrong with you, why you did what you did. You dated Jed because he said you were beautiful. And then Markus had kissed you after you drank too much at the holiday party. Gibb you went out with because Jed dumped you, and then Field after Gibb because you could do whatever you wanted, because you were above caring anymore. You say, “I’d like to try something different, Mom. Maybe teaching.” You tell her about the ads in the subway about making a difference.

You attend a birthday party. The host brings out Milton Bradley’s Operation, and everyone cheers when she extracts the spleen. You fail to extract anything. Later you overhear someone ask her in the kitchen, “What do you do?” You watch out of the corner of your eye as she replies unselfconsciously, “I wait tables.” Perhaps you, too, could wait tables, you think the next morning, as you stand still for thirty minutes, naked before an NYU drawing class, a class you took yourself a few years ago, before you graduated early. What was the rush?

You found your own T-shirt company. You are president and sole employee, and your apartment is filled with the unsold stock from the street fair where you ran into an ex and a former professor all in one day. They fingered your goods and neither of them bought anything. “I was in your class! I make them myself!” you said too quickly. Your ex said he liked the one that said “Second Base” and was trying to gauge whether or not it would fit his new girlfriend. He got her on the phone to ask her size, but then she didn’t want one after all, he explained, before winking at you and saying he had to go.

You get a job at a trendy restaurant you once went to on a date. You thought it would be fun to work at a place so chic. But your uniform is not chic and the wait staff, they correct you on your first day, must enter and exit through a special door in the rear. An older waiter who always gets the best tables, an actor who’s worked there for twenty years, takes you under his wing, shows you tricks with the ice machine, and tells you not to worry, that you’ll get used to it. You thank him with a mixture of gratitude and horror. You don’t want to get used to it.

You type forty words per minute, you lie. You believe you can learn PowerPoint. On days between job interviews, you smoke pot and watch Jerry Springer, Judge Judy, Judge Joe Brown, Dr. Phil, Oprah, Tyra, because “it’s so bad, it’s good,” you tell someone at a party. You call your parents to ask for more money. Your life, you think staring at Dr. Phil, is so good, it’s bad.

You avoid your friends. The successful ones make you feel ashamed, and the unsuccessful ones avoid you, too, for fear that all together you give off too strong an odor of failure. You prefer the company of strangers, those middle-aged drunks at the bar around the corner from your apartment, about whom you’ve decided to write a novel. You have the title and the last line already. Nowhere Is a Place. “Because you can’t leave nowhere unless nowhere is a place.” It’s about desolation and redemption at a bar around the corner from your narrator’s apartment.

You check your email: nothing. But then, a message from your parents: “We just got email! How’s the weather?”

You think of responding with a link to a weather website, but then worry it might throw off the delicate balance of your relationship with your parents. What would you talk about? “Mild with a chance of rain,” you write back. You want to write something hopeful, some bit of good news, something they can feel proud of. You want to tell them that things are looking up, that they shouldn’t worry. You type, “I got one of those new Sonicare toothbrushes you told me about. It’s revolutionized the way I clean my teeth.” You sign it “love” and press Send, unable to shake the feeling that your mom thinks you’re a loser. And no, it shouldn’t matter. But it does. It starts to.

“Getting a date,” a woman says on morning television, “is just like applying for a job.” This makes sense; no one will go out with you and no one wants to hire you.

You’ve heard a rumor that there is someone for everyone but are starting to worry that the one for you is ugly and stupid. What if you don’t like the one for you?

You’ve begun to take seriously magazine articles offering dating tips, when you come across an article entitled “Dating Tips for the Unemployed and Unsuccessful.” You read:

Singles are comprised of two distinct groups: the Miserable and the Non-Miserable. Recognizing to which category the object of your affection belongs is the first step toward a healthy romantic life.

Rule #1: Never date someone more or less miserable than you.

Your ideal partner is just as miserable as you are, though early on this may be difficult to discern. For in the beginning, you’ll both put on a good show, disguising your misery with a sprightly off-the-cuff wit (this has been rehearsed). And charmed by one another’s astonishing élan and the unusual receptiveness you’ve found with no one else, you’ll both begin to fall.

Now, having successfully tricked one another into believing you’re both happy, laughing persons, one of you will suggest that you share that happiness exclusively. You eagerly agree and are thrilled to find yourself the object of a love you suspect you do not deserve. She/he is just so great! you think, until you discover that your partner, whom you’d thought was way out of your league, whom you’d thought you’d stolen from the high shelf, was only faking it, just as you were. He or she, it turns out, is just as miserable as you. At first you are angry, but then anger gives way to relief. At last, you can share everything, including your misery. That is until one of you (you pray it’s not the other) achieves some modicum of success and leaves you even more miserable than before. But don’t despair—there are plenty of other miserable fish in the sea!

Rule #2: You will never fool anyone with your self-conscious quips about what you do.

Your wit will be your giveaway, as the most miserable in work offer the most creative responses. Individuals who are happy with their professional lives have no need for whimsical replies. They answer plainly, “I’m a bonds trader.” “I’m a teacher.” “I’m a doctor.” “A journalist.”

If someone answers, “I’m a blowfish,” rest assured this person is narrowly holding on. Furthermore, it will never work between the bonds trader and the blowfish. For just as you are suited to misery, the non-miserable are suited to one another. Even if you do manage a few dates with the bonds trader or any other non-miserable bachelor or bachelorette, your misery and the air of failure you’ve attempted to mask will eventually become apparent through the desperation of your wit and near-compulsive charm.

“Why must everything be a joke with you all the time? I asked you a simple question. What did you study in college?” the non-miserable boyfriend may ask during your final argument. “I told you. Theory and Engineering of Sweet Meats!” you answer devilishly, not wanting to tell him the truth: Medieval Poetry. “Why can’t you ever be serious?” he growls. “Are you suggesting my major wasn’t serious?” you purr.


Once you have disabused yourself of any notion of dating a non-miserable, the next step is learning to navigate among your miserable peers. The key to a lasting union lies in finding that unhappy single whose misery best matches your own.

Online dating sites are a treasure trove of the sad. Match, OKCupid, and Facebook are all great places to begin your search for a kindred loser. Once you’ve located a few nice pictures, scroll down their profile to where it says “Occupation.” Learn to decode these often figurative descriptions, and you’ll be well on your way to finding your perfect match. Let’s practice:

See Christine! Blond hair with a pretty smile. She has written under Occupation: “Being Christine.” This is to imply that Christine is down-to-earth, that she understands in a deep way that being herself is enough. Christine is lying. The truth is Christine hates being Christine, but feels she must get used to it; “everyone else is taken,” she once read in a fortune cookie. At the corners of Christine’s smile lie curls of defeat, but isn’t that what you found so charming in her photo?

John is smiling beside a sock puppet in suit and tie. Scroll down to Occupation, which reads: “I make toast in space.” John is deeply unhappy, so much so that he has mistaken it for happiness. He blinks a lot and is frequently confused, sometimes crying inexplicably at the conclusion of knock-knock jokes—he’ll claim he is crying because he is so happy to find “Orange” at the door. If you go to a diner with him, he will make the beaker of milk talk until you laugh out of an awkward politeness, which he’ll take for encouragement before continuing with the sugar packets.

Watch out for those who write “Secret Agent.” These charmless charmers are quick with ready-made phrases borrowed from the sitcoms and movies they favor, as a way of imbuing their steady stream of nervous chatter with the personality they fear they lack. “How you doin’?” the Secret Agent will ask you repeatedly in his best Joey Tribbiani voice, no matter how many times you answer that you are “fine.”

Longing for intimacy and eager to drop his disguise, the Secret Agent can morph into “the Real Me” in a matter of minutes. You’ll recognize the change when he begins talking of your “getting to know the real me,” as the primary characteristic of the Real Me is endlessly alluding to “the real me.” Other catchphrases of the Real Me: “I thought we were beyond that” and “I don’t play games.” What the Real Me really means is “I am bad at playing games. My saying I don’t play games is actually my best game. My Secret Agent secret weapon! ‘Yeah baby!’ Please be gentle. I’m very vulnerable right now. I can’t find a job and have had to move in with my parents.”

Need more help? Here’s a chart:

Occupations Decoded

If someone writes this: He/She really means this:
“I breed chinchillas with the hope of one day creating a super chinchilla.” “I’m studying for my real estate license and live at home.”
“I make pasta necklaces. Would you like one?” “I’m a barista and spend my free time training my fine blond hair into dreadlocks. I’m applying to graduate programs in ‘art therapy.’ My parents send me checks weekly, but I’m always ‘broke.’”
“I’m writing a screenplay about the psychological blocks of a gifted twenty-something male with a trust fund who is writing a novel about a gifted twenty-something male with a trust fund who is unemployed.” “I’ve been in therapy since my fifth birthday party, when my psychiatrist parents diagnosed my constipation as ‘withholding.’ Therapy takes up all my time. My parents send the rent directly to the landlord.”
“I’m pursuing an MFA in creative writing.” “I like the flexible hours of graduate school. Those years I spent working were really cutting into my drinking schedule. I hate my parents. My grandparents pay my rent.”
“I’m in the book trade.” “I’m a bookstore clerk and scoff at the titles successful customers ask me to find and correct my coworkers’ grammar in order to deflect attention from my own insecurities, which you’ll find are numerous and fascinating should I open up to you. But you have to earn it. I share a one-bedroom with five strangers I found on Craigslist and resent my friends whose parents pay their rent.”
“Freelance.” “I sell knives. I call my mother’s friends and ask them if they’d like to be able to cut a quarter in half without breaking a sweat. Born and raised in Manhattan, I’ve attended all the best schools. My parents moved me into the top-floor apartment of a building they own in order to get rid of a rent-stabilized sponge. I’m just doing them a favor.”
“Somali pirate” “I plunder ships on the open seas.”
“Professional cow-tipper” “I update my Facebook profile every hour with a new fake occupation. This is a good one. Ach! I just got poked! I love it! I’m gonna bite back with this awesome Vampire app! I live in the basement.”


But back to you! “What do you do?” That is, what are you going to say when the question comes up at that party tonight?

Feeling like you can’t face it? Like you might just stay in after all? Maybe stay in every night until you finish your novel? Until you’ve diagnosed the ills of your generation and found their cure in prose, so that when you do go out again, you’ll know who you are, and it won’t matter anymore how you answer, but it won’t feel too bad either when you say: “Novelist!”

Yes, you think, looking in the mirror as you throw on a comfortable sweatshirt. Stay in, it is! But to the deli first to buy a six-pack! And then, yes, of course, to your destiny in front of the computer, to your blank Word document entitled “The Novel.”

You crack open a beer and type a few paragraphs before deleting them. You don’t know what you’re doing, what should happen next, what’s important, if any of it is. You consider making the novel about desolation at a bar around the corner from your narrator’s apartment. You finish your last beer and consider going to the bar around the corner from your apartment for some research. But then you don’t; you’re already in your underwear and, besides, that lonely five-dollar bill in your wallet needs to last the week.

You stare at the blank document, a broad open boulevard inviting you to pass through, a door to your new life. The light from the screen reflects back on you like a spotlight.

You decide to go online awhile, just a little while, and log on to Facebook, where perhaps you and I might meet.

Look me up! I’m Iris. I have long brown hair, an uncertain smile, and become nervous when questioned directly about what I do. Scroll down. Under Occupation my job is listed as “You!” Which really means: “I like writing and talking about myself in the second person. If you go out with me, I’ll tell you all about yourself.”


Iris Smyles

Iris Smyles has published two books of fiction: Iris Has Free Time and Dating Tips for the Unemployed. Dating Tips for the Unemployed is a semi-finalist for the Thurber Prize for American Humor. Founder and editor of the web museum Smyles & Fish, she edited and wrote the afterword for the cult book, The Capricious Critic by Ari Martin Samsky, based on a column she commissioned for that site. Her short stories and essays have appeared in The Atlantic, The New York Times, BOMB, Paris Review Daily, Vogue, The Observer, McSweeny's Internet Tendency, and Best American Travel Writing 2015 among other publications, anthologies, and artist catalogs. She was a humor columnist for Splice Today and lives in New York and online at