8 New Yorkers Who Nearly Convinced Me Love Was Dead

Illustrated by Sydney Hass.
Dating in New York City is not a game for amateurs. Like any sport, it requires appropriate attire (a.k.a., an outfit that makes you look better than Amal Clooney), a strategy (developed over brunch with your friends), and a coach to keep you sane (your best friend, your roommate, or a trusty colleague). And, sometimes, if your pals become sick of hearing your dating woes and horror stories, you take drastic measures: You hire a recruiter — that is, a matchmaker.

Last year, I took on the interesting role of professional matchmaker, searching the city for eligible singles to set up with my clients. The job was incredibly intimate; I spent hours each day asking strangers prying questions about sexual attraction, commitment issues, infidelity, and painful heartbreak. Some people were a joy to work with. Others were lonely, bitter, and desperate; with their approach to dating, they're bound to be single forever.

See, I’m an optimist. I really want to believe that there's someone out there for everybody. But, these eight people managed to challenge my faith in love. If you're not coupled up this Valentine's Day, don't mourn your loss. Life could be worse — you could be dating one of these duds.
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Illustrated by Sydney Hass.
The Bollywood Star
One of the perks of matchmaking was that I met fascinating characters every day. When I had the chance to interview a Bollywood star — he was an actor, television host, and philanthropist — I was intrigued. Our conversation was, unsurprisingly, fabulous. He was charming and extroverted, told hilarious stories, and fit many of my client's preferences.

As he spoke, I went through the photographs on his Facebook profile and noticed that, in every single picture, he was flanked by young, hot girls. Not women. Bright-eyed young things with the kind of abs only seen in Hollywood-depicted sorority houses.

He was in his early 40s.

I politely waited for him to finish listing the international charity projects he was involved in before asking what age range he preferred to date. “You know, there are some very mature 18-year-olds.”

I just couldn't help but stare at the ones in his photos. They looked young enough to be his daughters. Pass!
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Illustrated by Sydney Hass.
The Serial Dater
“She should be tall, thin, breasty, 5'7" or above, and under 38," he rattled off without hesitation. “Implants are preferred. And, she should make a good salary on her own, unless she works in fashion or is a model, in which case, I wouldn't mind supporting her.”

Did he understand that I was a matchmaker, not a madam at a high-end escort service?

He was pasty white, sported thick-rimmed black glasses, and worked in private equity. Since his divorce six months ago, he had been on 150 dates, sometimes scheduling in three or four women on Saturdays. He'd give the “coveted" — as he described it — Saturday-evening spot to the best-looking one.

When I told him that none of my clients was up to his standards, he took it as a compliment to his fine tastes. Let's guess that he's probably still single.
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Illustrated by Sydney Hass.
The List-Maker
We all have a list of things we're looking for in the perfect partner: a sense of humor, a love of literature, the body and soul of Eddie Redmayne, right? Sure, it's fantastic to have a general sense of what you're looking for (common interests, shared life values), and you probably know that the person you’ll ultimately end up with is bound to deviate a little (or a lot) from your checklist.

After our extensive first meeting, the list-maker emailed me a five-page document detailing her dream man. A week later, she sent me another, slightly updated version. Two weeks later, another. There were five in total, with 12 sections, headings and subheadings, photo attachments, and a list of 31 potential hobbies (which included acrobatics, charity galas, and gardening) that she'd like to share with her match.

Date number one was with a guy I believed to fit an astonishing portion of her list. She wanted an accomplished skier who had lived abroad and made more than $200,000 a year? No problem — I set her up with a ski instructor turned hedge fund manager who spent a year living in Tokyo.

No good, apparently. He hadn't skied regularly for several years and had only lived abroad as a child, she told me. Dates two, three, and four went similarly, before I broke it to her that I was a matchmaker, not a man factory: I couldn't create her dream match out of thin air.
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Illustrated by Sydney Hass.
The Shallow Flake
It’s 2015. Before you go on a date, it's so easy to stalk the other person's Facebook, Twitter, Instagram, LinkedIn, Vine, and more. The prospect of going in totally blind is ludicrous. But, that’s exactly how the dates I set up worked. If you go in without any preconceived ideas or expectations of your match, you're forced to actually pay attention to what they say and ask thought-provoking questions.

One sneaky client broke my cardinal rule. With the limited information I had given him (her first name, industry, and neighborhood), he was still able to find her online. Fifteen minutes before they were supposed to meet, he called me in a panic: “Hannah, I can't go through with it. I found her Facebook. I'm not attracted to her at all.”

No. I did not interview dozens of prospects, arrange a time that worked for both of their insanely complicated schedules, and plan a creative date, only for him to back out. I put on my cheeriest voice and told him he must be looking at the wrong profile.

His voice shook. “I can't do it. She's not attractive. I'm not going to go.”

That's when I realized: A man's worst fear is being on a date with a woman he doesn't deem attractive enough. It's slimy, wretched, and disgusting — and, considering that women are often forgiving of a few extra pounds or a receding hairline, it's grossly unfair.
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Illustrated by Sydney Hass.
The Sleazy Cheater
One of my clients was a willowy woman in her early 50s who wore glittering diamonds head-to-toe. She was beautiful, easy to talk to, and owned a successful company; she was a total catch. But, when we met for our initial consultation at a bar, she fidgeted with the straw in her frozen margarita and quietly asked, “Do you really think there are any men who want a woman my age?” Then, she told me her story.

After 25 years of marriage, her husband left her for a girl half her age (barely older than their own daughter). She was devastated. She said she didn't even know any single men in their 50s, much less any men who would be interested in an age-appropriate woman. Her confidence was shot.

All summer, I set her up with men who swore up and down to me that they hadn't slept with a 20-year-old since they were in their 20s themselves. She met men for drinks, museum dates, and romantic walks through Central Park. For a woman who hadn't been on a date since Pretty in Pink was in theaters, that was no easy task. I'm proud of her.

But, as for her cheating, slimy ex-husband? He wasn't a client, thankfully, but I'll never forget him. Why bother setting someone like that up in the first place, I found myself wondering, if they're only going to end up cheating decades from now?
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Illustrated by Sydney Hass.
The Modelizer
If you didn't think modelizers existed outside of that episode of Sex and the City, welcome to New York: Some particularly deluded men — who happen to be well-connected, arrogant, and filthy rich — believe the only women worth dating are...models.

I don't even mean beautiful women. I mean six-feet-tall, leggy brunettes who don bikinis in Sports Illustrated's swimsuit edition and have Kate Upton on speed-dial. The modelizer I knew was a hopeless case; if you put a model in front of his face, he'd order her hundreds of roses, bathe her in compliments, and brag about how well-endowed he is. (Whether that was true or not, the model would never know. His bravado tended to repel them.)

I tried to set him up with one of the most gorgeous women I knew. She wasn't a model, but had dated her fair share of famous men. But, when I pulled up her most attractive photo, I watched his face contort in disgust. “You want me to date that cow? Never.”

Secretly, I was glad he wasn't interested — I would never wish anyone to have to spend an evening with him.
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Illustrated by Sydney Hass.
The Princess
Matchmaking was a crash course in how people view the intersection of dating, gender norms, and etiquette. I approached my job with the notion that the location and time of the date should be mutually convenient. When one person lived on the Upper East Side and the other in Williamsburg, for example, I would have them meet in Union Square.

The Princess rolled her eyes at that. She refused to plan a date a week in advance on the off chance that she might decide to go out with her girlfriends...even if she didn't have plans that night. When my client asked to move the date to a spot closer to his apartment in the East 80s, she called off the date. “If he can't come to the East 60s to see me, he's not worth my time," she said.

I think it's safe to assume she's still waiting to find her Prince Charming.
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Illustrated by Sydney Hass.
The Scarlett Johansson Fan Club
In news that will surprise absolutely no one, I discovered that your average New York man wants to have sex with Scarlett Johansson.

Let me be more specific: I interviewed hundreds of men. Most of them were Caucasian, in their 30s to 40s, and held a career in finance, law, or at a tech start-up. And, without fail, almost every single one told me that Scarlett Johansson was their dream girl. (Note: Variations included “Scarlett Johansson's head on a yoga-instructor body,” or “Scarlett Johansson's smile with Kim Kardashian's ass.”) There were days I interviewed ten men in a row and couldn't be bothered to write out her full name over and over in my notes — instead, my paperwork would be covered with "SJ...SJ...SJ."

Look, she is stunningly beautiful. I get it. But if every New York man is longing for ScarJo, they're going to be single for a very long time.

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