A Modern Matchmaker On True Love, Tinder, and How to Talk to Strangers

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Matchmaker Amy Van Doran is not herself today. Despite wearing a psychedelic print minidress, a pair of mod oversize glasses, and her signature neon orange bob (yes, it’s her real hair), something’s off, and within half an hour of my arrival at her East Williamsburg apartment, I find out why. Like many of her prospective clients, she’s going through a breakup.

Unlike the rest of us, however, Amy is in the business of love. She's the founder of the Modern Love Club, a matchmaking service for New York City's cool, creative class. Like its name suggests (it comes from the New York Times' popular Modern Love column), the Modern Love Club is somewhat of an antithesis to the traditional matchmaking construct, in which an older, rich male client seeks a woman who's—well, as long as she's under 35.

Instead, Amy handpicks 18 clients from the hundreds of letters she gets a day based on who she'd like to hang out with. "I'm a little bit in love with all my clients," she jokes. At the moment, those clients are mostly tech-y startup guys, fashion designers, a "hip surgeon lady" ('hip' as in 'cool,' not like the bone), and a professional poker player.

We spent an afternoon with Amy in her East Williamsburg home (and later at the nearby Fortunado Brothers bakery for cannolis), where she discussed everything from the impossibly high standards of New York men and her unique upbringing on "a junk yard in Florida," to how to chat dudes up on the subway.

I want to start with the name "Modern Love Club"—what makes a modern matchmaker?

Most matchmakers don't work with women, for one. Men hire them, and matchmakers go find girls based on what the men are looking for. The clients will often go, "I want a lady who's stunning, Ivy League–educated, five-foot-seven and size zero." I think that the other matchmaking companies tend to be more based on appearance, and though I definitely try to work with people that are marketable, they're maybe not marketable in the most obvious way.

"I’m always stuck in the sixties—you know, French New Wave films and Brigitte Bardot and that stuff. I’m happy if there’s a lot of color around. And clowns."

How do you go about picking them?

I mean, I’m a little bit in love with all my clients. That’s why I picked them! I get about 200 emails a day, and pick nine girls and nine guys that I think are amazing. I work with them for six months, and they date until they fall in love. Some people fall in love with the first person, other people fall in love with the seventh person, and some people go on 72 dates. And then, some people think they want a relationship, but they don’t actually want a relationship. It’s really interesting.

How do you spot the ones who aren't really in it "for the right reasons," to use a very lame Bachelor cliché?

If someone is extremely picky or if they’re on one level and are aiming way above what they can actually get, that seems to me like a defense mechanism. Even someone is like, "I’m too busy!"—if it was important, you’d make time. All I can do is introduce amazing people to amazing people. I try to pick people who are relationship-oriented. But then sometimes, people just don’t want to work with me—they'll say things like, "Oh my gosh, all your girlfriends are so cute and amazing, how am I going to pick one?" They’re always going after the next thing. That’s very much where people are at now, where they'll go, "That’s great, but what else do you have?" They’re not being present.

The standards of men in a city like New York are crazy. I’m like, 'Yo dude, you’re like 60 pounds overweight. I can’t get you what you can’t get in real life.'

Everyone is so worried about what they’re looking for that they’re not thinking about what they can actually land or who will be harmonious with them. They're thinking, "What’s the best thing I can do?" and "I see this hot girl. Therefore, I deserve her."

The standards of men in a city like New York are crazy. It seems like every single one wants a supermodel of a girl. No matter what physical form they’re in, they think they deserve the hottest, smartest, coolest girl. I’m like, "Yo dude, you’re like 60 pounds overweight. I can’t get you what you can’t get in real life. I can introduce you to cool people, but if they don’t want to date you, what am I supposed to do?"

I’m not in the business of trading good looks and youth and beauty for money. I cannot be involved in that. That’s why what I’m doing is different. It’s a pure form of matching people up—it’s not about "You’re young and hot, and you’re rich." Who wants to be loved because they have money? You can land the dopest 40-year-old who will appreciate you!

"For my bedroom, I wanted to do a mermaid-haunted-beach-brothel. Over there are some buffalo testicles I'm using as a plant holder. My friend Sara gave me the swan—she’s kind of witchy, and she blessed it in the moonlight someplace in New Mexico. An ex-boyfriend gave me those tiny jars. They're little human ear bones because he’s an ear, nose and throat surgeon. My mom’s deaf, and so as a gesture of love, he drilled out ear bones from a skull he was practicing on and jarred them for me because they’re the bones that my mom was missing in her ear."

Do you tell people this to their face? Like, do you say, "Um, hi, look in the mirror"?

I'll say something like, "You want to bring it? Okay, let’s bring it, but you better start going to the gym, and you better start wearing better outfits." If you want someone who is totally banging and in shape and successful, I'd hope that you’re the same. Whenever people try to outsource something and say things like, "Opposites attract! I can be really artistic but my partner has to be logical because I can’t do that." Well, no. Everyone constantly needs to be working on things and not say, "I’m just going to find a partner who can do that." It’s so funny—people come into my office and tell me they want someone with a sense of humor, but no one wants to date clowns or comedians. That’s another example of people setting themselves up for failure.

Do you give your clients any dating etiquette rules?

I have some guidelines. At the end of the day, any person is a reflection of me, so don’t be flaky, don’t cancel dates, show up on time, and treat it like an occasion. Wear an outfit. Don’t come in your gym clothes, find your positive attitude before you show up, be present, no cell phones out—that’s so rude! If you’re meeting for drinks, maybe don’t have more than two on an empty stomach, because we can get along with anyone when we’re drunk. Literally, I could fall in love with a street pole. But then sometimes I’m like, "Just get drunk and meet someone!" to someone that’s in a rut.

If it's through me, I prefer that people don’t hook up the first time they meet, because that period of lusting after a person for a long time makes it even better, then when you’re finally together, you’re like, "Yes!" It takes a little while to get that slow burn and that satisfaction. Don’t get me wrong, I think a quick fix is great, but it’s not the same as falling in love.

What gets me out of a rut is wearing silly shit and having a cute dog and lots of color around. And jumping around in the morning. Sugar helps.

Has your business changed since the popularity of Tinder and other instant matchmaking apps?

Maybe The Modern Love Club is busier because I’ve just been doing it longer, but the amount of people that are coming in is way more than at the beginning. I think it's because the number of people that are winning at Tinder is a small sect of the population, and a lot of others are getting ignored. I like Tinder, because it's similar to real life when you're thinking, "Oh, that person looks interesting, I want to meet them!" But some people are just better at taking photos or use Photoshop.

Originally, the people that were coming to me didn’t like using the Internet, and now, I'm getting people that are using the Internet too much and have burned out. I think matchmaking is becoming a lot more mainstream as people are realizing, "I just want to meet someone who someone else can vouch for." Online dating can be dehumanizing, because often it's just judging, judging, judging.

"I’m always on the search for a new caftan. I always wear this one—it started last summer, and I just kept cutting it."

Have you ever tried Tinder?

I tried it. Well, I swiped to the end of Tinder because I was having some insomnia, and also I was so curious. I interview nine people a day and hear their life stories, and it’s beautiful, but it’s also a little draining. So getting off of work and then sitting down and being like, "Tell me about yourself!" I was like, "Wait a second, I’ve been doing this all day!" So that was kind of weird.

Did you have a Tinder strategy? My friends who use it say not to talk to people for too long.

I didn’t talk to them a lot. My reasoning was that even if someone wasn’t for me, I could set them up with one of my clients. I still will bring people into the office if they look cool on Tinder or if we need a specific kind of match. I don’t care where the matches come from, I just want to find the best ones.

Originally, the people that were coming to me didn’t like using the Internet, and now, I'm getting people that are using the Internet too much and have burned out.

What about other dating apps?

I used Happn, too. It’s good! It sets you up to have gone on dates with all of your neighbors, so soon enough you'll be like, "I made out with you, and you, and you!" But it’s nice, because you date people that are close to you. I’m too lazy for OKCupid. And then other matchmakers have set me up, too. They weren’t setting me up with people I would normally go towards, which was okay because I can get along with anyone. I was being set up with finance guys—that sort of thing."

And who wants to date a finance guy?

I kind of do! I’ve been dating the sweet, artist types, which means that I have to be the practical one, and I don’t want to be practical. At one point I was like, "Maybe I'll just start dating my friends!"

How'd that go?

Probably one of my worst ideas ever. I should know better than this, but I don't. I've been dating, which has been interesting, since I've been in the single lady world. It's the first time I've been single in ten years—I was in a five-year relationship and then another five-year relationship. I'm like, "How do I date more than one person at a time? How do I negotiate that?" I'm obsessed with being honest with everyone, and so [the guys I date] are like, "You're just not supposed to tell us!"

"My friend installed this picture on my wall that she painted, and she said 'I think you’re the only person who will understand this painting.' I’m not sure that I understand the painting!"

Have you ever wanted to date one of your clients?

I’m not going to date anyone who comes into my office, even though those are the best people. It’s the same thing as your therapist hitting on you.

What's the best way to meet someone, then?

I think it's good to use the internet—just don't stay on the internet. Instead, say, "Oh hey, you just walked by my favorite cannoli shop, let's get a cannoli right now!"

What's your take on meeting people on the subway? Is that a no-go zone?

Oh god, no! You can meet people anywhere!

So... how do you go about that? I mean, for someone who isn't a professional matchmaker.

It literally does not matter. You just have to talk to people. I have one friend who's never done online dating, but he talks to more girls than anyone. He's not generically handsome—he just only pays attention to the people who say yes to him. And maybe he'll make three new friends in a day, but he'll talk to 100 people.

You just have to understand that your worth is important, and know that whoever you're approaching, you're doing them a favor. For me, before I go and talk to someone, I think in my head, "You're welcome!" It's almost like you're giving someone a gift.

Everybody says they want someone with a sense of humor, but no one wants to date comedians.

I think its becoming more difficult for people to talk to strangers. It's a muscle, so it starts with baby steps. Start with "I'm going to talk to my barista," or "I'm going to talk to this person at the laundromat," and then build up. I treat the world as if everyone is my friend. I think I'll always have a little Florida in me—that small-town mentality, where I'm thinking, "Oh, I haven't seen you around here, what are you doing here?" I act like I'm the regular at the bar, but the bar is the street. Because at the end of the day, if people are leaving their house, they want to be talked to. People don't go to bars to not be talked to.

Do you think it's easier for you, since you're already kind of a walking conversation piece?

I get to ham it up a lot for my job. I don't think it matters what a person is wearing as long as they're comfortable and happy. My favorite look on guys is a pair of nice blue jeans and a white T-shirt. Just as long as everyone’s doing what they want. I don't think being afraid has ever paid off for anyone.

Speaking of your style, I think I read something about you with a quote I really loved—you said, 'Everything you wear should have jokes built in.'

My sense of humor is getting more abstract. My philosophy lately has been that no one is going to amuse me for me. You know how clowns pull things out of their mouths? I almost want to do that. I feel like going to a party and putting jelly beans in my pocket and going like, "Oh are you looking for something?" and having jelly beans fly all over the place.

Everyone's trying to fit into the fashion world and they’re losing their sense of humor, but I think that sense of humor is everything. What gets me out of a rut is wearing silly shit and having a cute dog and lots of color around. And jumping around in the morning. Sugar helps.

"A lot of my clothes are my grandma’s [right, middle shelf]. She was from this part in Florida where everyone was in the circus. Circus performers would just live there since it was the last stop. Then she dropped out and became a barber. She went from nice girl to crazy Janis Joplin like howls at wolves and rides motorcycles."

Where do you think that comes from—your particular sense of style?

I grew up on a junkyard in Florida. My grandpa was an anarchist junk man that eventually became a circus performer. My mom, who's deaf, was too young to be a mom, so my grandparents adopted me. I didn't talk until my grandparents adopted me.

A lot of clothes are my grandma's—she was from this part in Florida where everyone was in the circus. It was the last stop on the train so circus performers would just live there. She started to perform but got sick of it, so she dropped out and became a barber. She went from nice girl to a crazy Janis Joplin who howls at wolves and rides motorcycles—and my grandpa was twelve years younger than her.

People sometimes think that I'm being eccentric, but it's just how I was raised. I actually think that I came out a lot less eccentric than the rest of my family. I feel very normal. And everyone else is like, "What is this act?" and I'm like, "It's not!"

My favorite question, and the question I don’t have the answer to, is 'How do you make love stay?'

What's the best piece of advice you give to people looking for love?

Don’t wait. Don't say, "Maybe I’ll meet someone after I’ve lost 40 pounds." You’re great as you are, you just need to start talking to people. You can lose the forty pounds as you’re doing it.

I think that none of us need anything—everyone has everything that they need to face themselves and say, "Here I am. I’m great. You’re welcome." If you want to turn that thing on, there are people around you. You go to work. I’m sure someone has a crush on you there! If you’re pleasant to be around, people will want to be around you. And you only need to find one person. Not everyone has to love you.

Are there any questions you have a difficult time answering?

I think my favorite question, and the question I don’t have the answer to, is "How do you make love stay?" Because I don’t know how to make love stay. If you put people in love through brain scanners, you see the same neurological pathways as those of someone who’s addicted to cocaine. There’s no difference. If you think of love that way—that chemical kind of doped up state—know that it’s going to go away. It’ll go away in two years, tops. You know why? It's because biologically, two years is enough time to become impregnated and for the man to not leave before the baby is old enough to survive the infancy.

But the more interesting stuff is like what happens when you get really deep with a person. How do you stay in love with a person—maybe you observe them at a distance, instead of being so close. When you’re out, watch your lover or partner from across the room and re-fall in love with them. Wake up every day and instead of thinking, "Do I feel loved?" ask yourself, "What could I do to make my partner feel loved? In which ways can I find new ways to love you?" It’s almost like a creative challenge to yourself.

Another thing is not to confuse an on-and-off relationship where you're constantly anxious with love. Your hands are sweaty, your heart is palpitating, but that’s not love. That’s anxiety. A lot of people have that girl that won’t be there, that boy who doesn't call—that drama in a relationship where you think you're in love. No, you don’t love him. You’re stressed out.

For me, the feeling of being in love is the feeling of calm. It’s not mania, which is not unlike drugs. If you want that, go do some drugs. But the mania is going to go away. But if what you’re left with is someone that you feel calm and lovely around, and they have values aligned with your values and goals aligned with your goals, it’s not their job to keep you in love with them, it’s your job to figure out ways to keep loving them.

Have you coached a lot of clients through breakups?

There’s nothing worse than finding love, feeling it, and not being able to hold it. That’s part of the human condition right? It’s funny, no one wants to tell the truth about things. But for me with my last big breakup, the fact of the matter was that I cared about the person more than they cared about me. He just didn’t love me enough. And that sucks. It's the worst thing. But then at the end of the day, I have to think to myself that maybe I just wasn’t to his taste. It wasn’t right, there’s nothing wrong with me.

It’s hard. You can do yoga, you can find religion, you can smoke, you can have sex with everyone, but there’s nothing you can do to outrun it. That's just what it is to be a human being, right? Something hurts, but you keep doing it because there’s nothing more important than connecting with other human beings. That’s why we’re on this planet. Stay open, and try to be your most positive self. There’s always going to be someone else.

Do you think that everyone can find one person that they can spend their lives with?

I think so. The feeling that you can’t find someone is the worst feeling in the world. I think everyone needs to think that exists. You just keep moving forward. There are multiple people for multiple people.

That's a nice thought.

It’s a good job. I get to hear nine people’s life stories a day about the thing that’s the most important to them. I think when I first started, I was a lot lighter and more zany. And now, I’m a little bit more serious with what I’m doing. I have some theories about things. I'm more serious because love is the most important thing in the world. I just don’t think that anyone should ever be in a situation where if they want to meet someone they can’t. Being alone is hard, and it’s important that anyone who wants to find love can. Because I can’t think of anything that’s more important than that.

This interview has been edited and condensed.